1-(4-methoxybenzoyl)pyrrolidin-2-one [Aniracetam] by Asch

Reaxys

PubChem

eMolecules

Reactions (17)

Substances (2)

Page 1 of 1

Citations (111)

Structure

Structure/Compound Data Chemical Name: aniracetam Reaxys Registry Number: 4807205

CAS Registry Number: 72432-10-1 Type of Substance: heterocyclic Molecular Formula: C12H13NO3

Linear Structure Formula: C12H13NO3

Molecular Weight: 219.24 InChI Key: ZXNRTKGTQJPIJK-UHFFFAOYSA-N

N° of preparations All Preps | All Reactions 13 prep out of 16 reactions.

Synthesize | Hide Details Find similar Chemical Names and Synonyms aniracetam, 1-(4-methoxybenzoyl)-2-pyrrolidinone, Aniracetam, 1-(p-methoxybenzoyl)-2-pyrrolidinone, 1-anisoyl-2-pyrrolidinone, 1-(4methoxybenzoyl)pyrrolidin-2-one, 1-(4-Anisoyl)pyrrolidin-2-one Identification Substance Label (13) Label

Reference

Morofuji, Tatsuya; Shimizu, Akihiro; Yoshida, Jun-Ichi

Journal of the American Chemical Society, 2015 , vol. 137, # 31 p. 9816 - 9819 Title/Abstract Full Text View citing articles Show Details

Li, Haoquan; Dong, Kaiwu; Neumann, Helfried; Beller, Matthias

Angewandte Chemie - International Edition, 2015 , vol. 54, # 35 p. 10239 - 10243 Angew. Chem., 2015 , vol. 127, # 35 p. 10377 - 10381,5 Title/Abstract Full Text View citing articles Show Details

Available Data

N° of ref.

Identification Physical Data (11) Spectra (7) Bioactivity (79) Use/Application (61)

111

3ag

Zhang, Jian; Hong, Soon Hyeok

Organic Letters, 2012 , vol. 14, # 17 p. 4646 - 4649 Title/Abstract Full Text View citing articles Show Details

Tab.1

Naftalin, Richard J.; Cunningham, Philip; Afzal-Ahmed, Iram

British Journal of Pharmacology, 2004 , vol. 142, # 3 p. 594 - 608 Title/Abstract Full Text View citing articles Show Details

ani

Lawrence, J. Josh; Brenowitz, Stephan; Trussell, Laurence O.

Molecular Pharmacology, 2003 , vol. 64, # 2 p. 269 - 278 Title/Abstract Full Text View citing articles Show Details

Zarrinmayeh; Bleakman; Gates; Yu; Zimmerman; Ornstein; McKennon; Arnold; Wheeler; Skolnick

Journal of medicinal chemistry, 2001 , vol. 44, # 3 p. 302 - 304 Title/Abstract Full Text View citing articles Show Details

Karimi; Kihlberg; Langstroem

Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 13 p. 1528 - 1531 Title/Abstract Full Text View citing articles Show Details

Wu, X.Y.; Eshun, G.; Zhou, Y.

Journal of Pharmaceutical Sciences, 1998 , vol. 87, # 5 p. 594 - 598 Title/Abstract Full Text Show Details

Ogiso, Taro; Uchiyama, Kaori; Suzuki, Hiroko; Yoshimoto, Mika; Tanino, Tadatoshi; Iwaki, Masahiro; Satoshi, Uno

Biological and Pharmaceutical Bulletin, 2000 , vol. 23, # 4 p. 482 - 486 Title/Abstract Full Text View citing articles Show Details

Anir

Johansen, Tina H.; Chaudhary, Archana; Verdoorn, Todd A.

Molecular Pharmacology, 1995 , vol. 48, # 5 p. 946 - 955 Title/Abstract Full Text View citing articles Show Details

Merck Index 700

Pizzi; Consolandi; Memo; Spano

European Journal of Pharmacology, 1995 , vol. 275, # 3 p. 311 - 314 Title/Abstract Full Text View citing articles Show Details

MERCK 700

Hamelin; Lehmann

European Journal of Pharmacology, 1995 , vol. 281, # 3 p. R11-R13 Title/Abstract Full Text View citing articles Show Details

Tab.1,run 25(Merck:700)

Noyer, Michel; Gillard, Michel; Matagne, Alain; Henichart, Jean-Pierre; Wuelfert, Ernst

European Journal of Pharmacology, 1995 , vol. 286, # 2 p. 137 - 146 Title/Abstract Full Text View citing articles Show Details

M 700

Petitet; Blanchard; Doble

European Journal of Pharmacology - Molecular Pharmacology Section, 1995 , vol. 291, # 2 p. 143 - 151 Title/Abstract Full Text View citing articles Show Details

Patent-Specific Data (2) Related Markush Structure (RN)

Location in Patent

Reference

Page/Page column

Zaklady Farmaceutyczne Polpharma SA; Szramka, Roman; Sagol, Karol; Poojari, Krishna

Patent: EP2604592 B1, 2014 ; Title/Abstract Full Text Show Details

Cha, Albert

Patent: US2006/241144 A1, 2006 ;

11335659

Title/Abstract Full Text Show Details

Physical Data Melting Point (1) Melting Point

Solvent (Melting Point)

Reference

120 °C

ethanol

Bandoli, Giuliano; Nicolini, Marino; Lumbroso, Henri; Grassi, Antonio; Pappalardo, Giuseppe C.

Journal of Molecular Structure, 1987 , vol. 160, p. 297 - 310 Title/Abstract Full Text View citing articles Show Details

Density (1)

Density

Type (Density)

Reference

1.35 g·cm-3

crystallographic

Bandoli, Giuliano; Nicolini, Marino; Lumbroso, Henri; Grassi, Antonio; Pappalardo, Giuseppe C.

Journal of Molecular Structure, 1987 , vol. 160, p. 297 - 310 Title/Abstract Full Text View citing articles Show Details

Conformation (1) Object of Investigation

Reference

Conformation

Bandoli, Giuliano; Nicolini, Marino; Lumbroso, Henri; Grassi, Antonio; Pappalardo, Giuseppe C.

Journal of Molecular Structure, 1987 , vol. 160, p. 297 - 310 Title/Abstract Full Text View citing articles Show Details

Crystal Phase (1) Description (Crystal Phase) Crystal structure determination

Comment (Crystal Phase)

Reference

β=94.5 grad, a=17.06 Angstroem, b=9.56 Angstroem, c=6.67 Angstroem, n=4. Method of determination: Single Crystal X-ray Diffraction

Bandoli, Giuliano; Nicolini, Marino; Lumbroso, Henri; Grassi, Antonio; Pappalardo, Giuseppe C.

Journal of Molecular Structure, 1987 , vol. 160, p. 297 - 310 Title/Abstract Full Text View citing articles Show Details

Crystal Property Description (1) Colour & Other Properties

Location

Reference

yellow

supporting information

Zhang, Jian; Hong, Soon Hyeok

Organic Letters, 2012 , vol. 14, # 17 p. 4646 - 4649 Title/Abstract Full Text View citing articles Show Details

Crystal System (1) Crystal System

Reference

monoclinic

Bandoli, Giuliano; Nicolini, Marino; Lumbroso, Henri; Grassi, Antonio; Pappalardo, Giuseppe C.

Journal of Molecular Structure, 1987 , vol. 160, p. 297 - 310 Title/Abstract Full Text View citing articles Show Details

Electrical Moment (1) Description (Electrical Moment)

Moment (Electrical Moment)

Temperature (Electrical Moment)

Solvent (Electrical Moment)

Dipole moment

2.69 D

30 °C

benzene

Reference Bandoli, Giuliano; Nicolini, Marino; Lumbroso, Henri; Grassi, Antonio; Pappalardo, Giuseppe C.

Journal of Molecular Structure, 1987 , vol. 160, p. 297 - 310 Title/Abstract Full Text View citing articles Show Details

Interatomic Distances and Angles (1) Description

Reference

Interatomic distances and angles

Bandoli, Giuliano; Nicolini, Marino; Lumbroso, Henri; Grassi, Antonio; Pappalardo, Giuseppe C.

Journal of Molecular Structure, 1987 , vol. 160, p. 297 - 310 Title/Abstract Full Text View citing articles Show Details

Partition octan-1-ol/water (MCS) (1) log POW

Location

Comment (Partition octan-1-ol/water (MCS))

Reference

0.27

7.4

supporting information

aq.buffer

Gunaydin, Hakan

ACS Medicinal Chemistry Letters, 2016 , vol. 7, # 1 p. 89 - 93 Title/Abstract Full Text View citing articles Show Details

Solubility (MCS) (1) Solubility

Saturation

Temperature (Solubility (MCS))

Solvent (Solubility (MCS))

Reference

0.10962 g·l-1

in solution

25 °C

phosphate buffer

Alelyunas, Yun W.; Empfield, James R.; McCarthy, Dennis; Spreen, Russell C.; Bui,

Khanh; Pelosi-Kilby, Luciana; Shen, Cindy

Bioorganic and Medicinal Chemistry Letters, 2010 , vol. 20, # 24 p. 7312 - 7316 Title/Abstract Full Text View citing articles Show Details

Space Group (1) Space Group

Reference

Bandoli, Giuliano; Nicolini, Marino; Lumbroso, Henri; Grassi, Antonio; Pappalardo, Giuseppe C.

Journal of Molecular Structure, 1987 , vol. 160, p. 297 - 310 Title/Abstract Full Text View citing articles Show Details

Spectra NMR Spectroscopy (6) Description (NMR Spectroscopy)

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

Frequency (NMR Spectroscopy)

Chemical shifts Spectrum

chloroform-d1

Chemical shifts Spectrum

13C

Chemical shifts Spectrum

Location

Reference

300 MHz

supporting information

Li, Haoquan; Dong, Kaiwu; Neumann, Helfried; Beller, Matthias

Angewandte Chemie - International Edition, 2015 , vol. 54, # 35 p. 10239 - 10243 Angew. Chem., 2015 , vol. 127, # 35 p. 10377 10381,5 Title/Abstract Full Text View citing articles Show Details

chloroform-d1

75 MHz

supporting information

Li, Haoquan; Dong, Kaiwu; Neumann, Helfried; Beller, Matthias

Angewandte Chemie - International Edition, 2015 , vol. 54, # 35 p. 10239 - 10243 Angew. Chem., 2015 , vol. 127, # 35 p. 10377 10381,5 Title/Abstract Full Text View citing articles Show Details

chloroform-d1

supporting information

Zhang, Jian; Hong, Soon Hyeok

Organic Letters, 2012 , vol. 14, # 17 p. 4646 - 4649 Title/Abstract Full Text View citing articles Show Details

Chemical shifts Spectrum

13C

chloroform-d1

supporting information

Zhang, Jian; Hong, Soon Hyeok

Organic Letters, 2012 , vol. 14, # 17 p. 4646 - 4649 Title/Abstract Full Text View citing articles Show Details

Chemical shifts

dimethylsulfoxide-d6

300 MHz

Karimi; Kihlberg; Langstroem

Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 13 p. 1528 - 1531 Title/Abstract Full Text View citing articles Show Details

Chemical shifts

13C

dimethylsulfoxide-d6

Karimi; Kihlberg; Langstroem

Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 13 p. 1528 - 1531 Title/Abstract Full Text View citing articles Show Details

Mass Spectrometry (1) Description (Mass Spectrometry)

Location

Reference

high resolution mass spectrometry (HRMS) electrospray ionisation (ESI) spectrum

supporting information

Li, Haoquan; Dong, Kaiwu; Neumann, Helfried; Beller, Matthias

Angewandte Chemie - International Edition, 2015 , vol. 54, # 35 p. 10239 - 10243 Angew. Chem., 2015 , vol. 127, # 35 p. 10377 - 10381,5 Title/Abstract Full Text View citing articles Show Details

Bioactivity Pharmacological Data (72) 1 of 72

Comment (Pharmacological Data)

Bioactivities present

Reference

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Comment (Pharmacological Data)

Bioactivities present

Reference

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Molecular Pharmacology, 1995 , vol. 48, # 5 p. 946 - 955 Title/Abstract Full Text View citing articles Show Details

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European Journal of Pharmacology, 1995 , vol. 275, # 3 p. 311 - 314 Title/Abstract Full Text View citing articles Show Details

Wu, X.Y.; Eshun, G.; Zhou, Y.

Journal of Pharmaceutical Sciences, 1998 , vol. 87, # 5 p. 594 - 598 Title/Abstract Full Text Show Details

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European Journal of Pharmacology, 1995 , vol. 281, # 3 p. R11-R13 Title/Abstract Full Text View citing articles Show Details

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European Journal of Pharmacology, 1995 , vol. 286, # 2 p. 137 - 146 Title/Abstract Full Text View citing articles Show Details

Petitet; Blanchard; Doble

European Journal of Pharmacology - Molecular Pharmacology Section, 1995 , vol. 291, # 2 p. 143 - 151 Title/Abstract Full Text View citing articles Show Details

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Chemical and Pharmaceutical Bulletin, 2000 , vol. 48, # 8 p. 1121 - 1124 Title/Abstract Full Text View citing articles Show Details

Zarrinmayeh; Bleakman; Gates; Yu; Zimmerman; Ornstein; McKennon; Arnold; Wheeler; Skolnick

Journal of medicinal chemistry, 2001 , vol. 44, # 3 p. 302 - 304 Title/Abstract Full Text View citing articles Show Details

Zivkovic; Thompson; Bertolino; Uzunov; DiBella; Costa; Guidotti

Journal of Pharmacology and Experimental Therapeutics, 1995 , vol. 272, # 1 p. 300 - 309 Title/Abstract Full Text View citing articles Show Details

Karimi; Kihlberg; Langstroem

Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 13 p. 1528 - 1531 Title/Abstract Full Text View citing articles Show Details

Ogiso, Taro; Uchiyama, Kaori; Suzuki, Hiroko; Yoshimoto, Mika; Tanino, Tadatoshi; Iwaki, Masahiro; Satoshi, Uno

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3 of 72

Comment (Pharmacological Data)

Bioactivities present

Reference

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Nippon Suisan Kaisha, Ltd.

Patent: US5955505 A1, 1999 ; Title/Abstract Full Text Show Details

The Regents of the University of California

Patent: US6030968 A1, 2000 ; Title/Abstract Full Text Show Details

YOSHII, MITSUNOBU; WATABE, SHIGEO

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Tian, Yuan; Zhang, Jing-Jing; Feng, Shu-Dan; Zhang, Zun-Jian; Chen, Yun

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ONO PHARMACEUTICAL CO., LTD.

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Grove, Simon J. A.; Jamieson, Craig; MacLean, John K. F.; Morrow, John A.; Rankovic, Zoran

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Alelyunas, Yun W.; Empfield, James R.; McCarthy, Dennis; Spreen, Russell C.; Bui, Khanh; Pelosi-Kilby, Luciana; Shen, Cindy Bioorganic and Medicinal Chemistry Letters, 2010 , vol. 20, # 24 p. 7312 - 7316 Title/Abstract Full Text View citing articles Show Details

Mueller, Rudolf; Li, Yong-Xin; Hampson, Aidan; Zhong, Sheng; Harris, Clayton; Marrs, Christopher; Rachwal, Stanislaw; Ulas, Jolanta; Nielsson, Lena; Rogers, Gary

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Zhang, Jian; Hong, Soon Hyeok

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4 of 72

Comment (Pharmacological Data)

Bioactivities present

Reference

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Chen, Haijun; Wang, Cheng Z.; Ding, Chunyong; Wild, Christopher; Copits, Bryan; Swanson, Geoffrey T.; Johnson, Kenneth M.; Zhou, Jia

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Nishizaki, Tomoyuki; Matsumura, Takuro

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Zhao, Xilong; Kuryatov, Alexander; Lindstrom, Jon M.; Yeh, Jay Z.; Narahashi, Toshio

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Ogiso, Taro; Iwaki, Masahiro; Tanino, Tadatoshi; Ikeda, Kazuyuki; Paku, Tsuyoshi; Horibe, Yoshihide; Suzuki, Hiroko

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Endo; Tajima; Yamada; Igata; Yamamoto; Tsuchida; Nakashima; Suzuki; Ikari; Iguchi

Behavioural Brain Research, 1997 , vol. 83, # 1-2 p. 243 - 244 Title/Abstract Full Text View citing articles Show Details

Pittaluga; Pattarini; Raiteri

European Journal of Pharmacology, 1995 , vol. 272, # 2-3 p. 203 - 209 Title/Abstract Full Text Show Details

Noyer; Gillard; Matagne; Henichart; Wulfert

European Journal of Pharmacology, 1995 , vol. 286, # 2 p. 137 - 146

Title/Abstract Full Text Show Details

Zivkovic; Thompson; Bertolino; Uzunov; DiBella; Costa; Guidotti

Journal of Pharmacology and Experimental Therapeutics, 1995 , vol. 272, # 1 p. 300 - 309 Title/Abstract Full Text View citing articles Show Details

Angelucci; Calvisi; Catini; Cosentino; Cozzolino; De Witt; Ghirardi; Giannessi; Giuliani; Guaraldi; Misiti; Ramacci; Scolastico; Tinti

Journal of Medicinal Chemistry, 1993 , vol. 36, # 11 p. 1511 - 1519 Title/Abstract Full Text Show Details

Worms; Kan; Steinberg; Terranova; Perio; Biziere

Naunyn-Schmiedeberg's Archives of Pharmacology, 1989 , vol. 340, # 4 p. 411 - 418 Title/Abstract Full Text Show Details

Foltyn; Lucker; Schnitker; Wetzelsberger

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Cumin; Bandle; Gamzu; Haefely

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5 of 72

Comment (Pharmacological Data)

Bioactivities present

Reference

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F. Hoffman-La Roche data on file B-104'488, 1984, 1984 Full Text Show Details

Clarke's Analysis of Drugs and Poisons Full Text Show Details

Yakuri to Chiryo Pharmacol. Ther., vol. 14 Full Text Show Details

E Toja; C Gorini; C Zirotti; F Barzaghi; G Galliani

European journal of medicinal chemistry, 1991 , vol. 26, p. 415 - 422 Title/Abstract Full Text Show Details

E. Graindorge; P. Francotte; S. Boverie; P. de Tullio; B. Pirotte

Current Medicinal Chemistry: Central Nervous System Agents, 2004 , vol. 4, # 2 p. 95 - 103 Title/Abstract Full Text Show Details

http://www2.siri.org/msds/tox/f/q120/q599.html Full Text Show Details

http://www.mindandmuscle.net/content/page-242.html Full Text Show Details

Zaklady Farmaceutyczne Polpharma SA; Szramka, Roman; Sagol, Karol; Poojari, Krishna

Patent: EP2604592 B1, 2014 ; Title/Abstract Full Text Show Details

Morofuji, Tatsuya; Shimizu, Akihiro; Yoshida, Jun-Ichi

Journal of the American Chemical Society, 2015 , vol. 137, # 31 p. 9816 - 9819 Title/Abstract Full Text View citing articles Show Details

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Comment (Pharmacological Data)

Bioactivities present

Reference

Li, Haoquan; Dong, Kaiwu; Neumann, Helfried; Beller, Matthias

Angewandte Chemie - International Edition, 2015 , vol. 54, # 35 p. 10239 - 10243 Angew. Chem., 2015 , vol. 127, # 35 p. 10377 - 10381,5 Title/Abstract Full Text View citing articles Show Details

Lynch Gary S.; Rogers Gary A.

Patent: EP1156043 A2, 2003 ; Title/Abstract Full Text Show Details

Gary S. Lynch; Gary A. Rogers

Patent: US5852008 A, 1998 ; Title/Abstract Full Text Show Details

ROGERS Gary A.; LYNCH Gary S.

Patent: WO1994/2475 A1, 1994 ; Title/Abstract Full Text Show Details

Peter Van Der Klish; Gary Lynch

Patent: US2002/45612 A1, 2002 ; Title/Abstract Full Text Show Details

Peter Van Der Klish; Gary Lynch

Patent: US6620808 B2, 2003 ; Title/Abstract Full Text Show Details

VAN DER KLISH Peter; LYNCH Gary

Patent: WO1998/50036 A1, 1998 ; Title/Abstract Full Text Show Details

John Larson; Gary Lynch; Gary A. Rogers

Patent: US5773434 A, 1998 ; Title/Abstract Full Text Show Details

ROGERS Gary A; LARSON John; LYNCH Gary

Patent: WO1997/7799 A1, 1997 ; Title/Abstract Full Text Show Details

Gunaydin, Hakan

ACS Medicinal Chemistry Letters, 2016 , vol. 7, # 1 p. 89 - 93 Title/Abstract Full Text View citing articles Show Details

Changeux, Jean-Pierre; Christopoulos, Arthur

Cell, 2016 , vol. 166, # 5 p. 1084 - 1102 Title/Abstract Full Text Show Details

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Effect (Pharmacological Data)

transporter; stimulation of

Species or TestSystem (Pharmacological Data)

HEK293-Flp-In cells; genetically modified/infected with: human OCT2

Concentration (Pharmacological Data)

20 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO

Further Details (Pharmacological Data)

OCT2: organic cation transporter 2 (solute carrier 22A2); HEK: human embryonic kidney; fluorescent probe substrate: 4-(4(dimethylamino)styryl)-N-methyl-pyridinium (ASP+) (5 μmol/l); high-throughput assay; fluorimetry; stimulation rate related to: OCT2

Type (Pharmacological Data)

stimulation rate

Value of Type (Pharmacological Data)

0.8 percent

Location

supporting information

Reference

Kido, Yasuto; Matsson, Paer; Giacomini, Kathleen M.

Journal of Medicinal Chemistry, 2011 , vol. 54, # 13 p. 4548 - 4558 Title/Abstract Full Text View citing articles Show Details

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Effect (Pharmacological Data)

transporter; stimulation of

Species or TestSystem (Pharmacological Data)

HEK293-Flp-In cells; genetically modified/infected with: human OCT2

Concentration (Pharmacological Data)

20 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO

Further Details (Pharmacological Data)

Results

molecular target: human OCT2

Location

supporting information

Reference

Kido, Yasuto; Matsson, Paer; Giacomini, Kathleen M.

Journal of Medicinal Chemistry, 2011 , vol. 54, # 13 p. 4548 - 4558 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

enzyme activity; inhibition of

Species or TestSystem (Pharmacological Data)

fatty acid amide hydrolase of human

Concentration (Pharmacological Data)

1 μmol/l

Type (Pharmacological Data)

percent inhibition

Value of Type (Pharmacological Data)

-15.98 - 4.06 percent

Location

supporting information

Reference

Vincent, Fabien; Nguyen, Margaret T.; Emerling, Daniel E.; Kelly, Michael G.; Duncton, Matthew A.J.

Bioorganic and Medicinal Chemistry Letters, 2009 , vol. 19, # 23 p. 6793 - 6796 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

enzyme activity; inhibition of

Species or TestSystem (Pharmacological Data)

fatty acid amide hydrolase of human

Concentration (Pharmacological Data)

1 μmol/l

Results

molecular target: fatty acid amide hydrolase

Location

supporting information

Reference

Vincent, Fabien; Nguyen, Margaret T.; Emerling, Daniel E.; Kelly, Michael G.; Duncton, Matthew A.J.

Bioorganic and Medicinal Chemistry Letters, 2009 , vol. 19, # 23 p. 6793 - 6796 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

pharmacokinetics

Species or TestSystem (Pharmacological

human

Data)

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13 of 72

Sex

male

Route of Application

peroral

Concentration (Pharmacological Data)

400 mg

Kind of Dosing (Pharmacological Data)

2*200 mg/capsule

Further Details (Pharmacological Data)

maximum plasma concentration (Cmax); Cmax related to: plasma

Type (Pharmacological Data)

Cmax

Value of Type (Pharmacological Data)

8.75 ng/ml

Reference

Tian, Yuan; Zhang, Jing-Jing; Feng, Shu-Dan; Zhang, Zun-Jian; Chen, Yun

Arzneimittel-Forschung/Drug Research, 2008 , vol. 58, # 10 p. 497 - 500 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

pharmacokinetics

Species or TestSystem (Pharmacological Data)

human

Sex

male

Route of Application

peroral

Concentration (Pharmacological Data)

400 mg

Kind of Dosing (Pharmacological Data)

2*200 mg/capsule

Further Details (Pharmacological Data)

time to Cmax (tmax); tmax related to: plasma

Type (Pharmacological Data)

tmax

Value of Type (Pharmacological Data)

0.4 h

Reference

Tian, Yuan; Zhang, Jing-Jing; Feng, Shu-Dan; Zhang, Zun-Jian; Chen, Yun

Arzneimittel-Forschung/Drug Research, 2008 , vol. 58, # 10 p. 497 - 500 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

pharmacokinetics

Species or TestSystem (Pharmacological Data)

human

Sex

male

Route of Application

peroral

Concentration (Pharmacological Data)

400 mg

Kind of Dosing (Pharmacological

2*200 mg/capsule

Data)

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Further Details (Pharmacological Data)

halflife time (elimination) (t1/2); t1/2 related to: plasma

Type (Pharmacological Data)

t1/2

Value of Type (Pharmacological Data)

0.47 h

Reference

Tian, Yuan; Zhang, Jing-Jing; Feng, Shu-Dan; Zhang, Zun-Jian; Chen, Yun

Arzneimittel-Forschung/Drug Research, 2008 , vol. 58, # 10 p. 497 - 500 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

pharmacokinetics

Species or TestSystem (Pharmacological Data)

human

Sex

male

Route of Application

peroral

Concentration (Pharmacological Data)

400 mg

Kind of Dosing (Pharmacological Data)

2*200 mg/capsule

Further Details (Pharmacological Data)

mean residence time (MRT); MRT related to: plasma

Type (Pharmacological Data)

MRT

Value of Type (Pharmacological Data)

0.77 h

Reference

Tian, Yuan; Zhang, Jing-Jing; Feng, Shu-Dan; Zhang, Zun-Jian; Chen, Yun

Arzneimittel-Forschung/Drug Research, 2008 , vol. 58, # 10 p. 497 - 500 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

pharmacokinetics

Species or TestSystem (Pharmacological Data)

human

Sex

male

Route of Application

peroral

Concentration (Pharmacological Data)

400 mg

Kind of Dosing (Pharmacological Data)

2*200 mg/capsule

Further Details (Pharmacological Data)

area under the curve from time zero to 2.5 h (AUC0-2.5); AUC0-2.5 related to: plasma

Type (Pharmacological Data)

AUC0-2.5

Value of Type (Pharmacological

4.53 ng*h/ml

Data)

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Reference

Tian, Yuan; Zhang, Jing-Jing; Feng, Shu-Dan; Zhang, Zun-Jian; Chen, Yun

Arzneimittel-Forschung/Drug Research, 2008 , vol. 58, # 10 p. 497 - 500 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

pharmacokinetics

Species or TestSystem (Pharmacological Data)

human

Sex

male

Route of Application

peroral

Concentration (Pharmacological Data)

400 mg

Kind of Dosing (Pharmacological Data)

2*200 mg/capsule

Further Details (Pharmacological Data)

area under the curve (AUC); AUC related to: plasma

Type (Pharmacological Data)

AUC

Value of Type (Pharmacological Data)

4.62 ng*h/ml

Reference

Tian, Yuan; Zhang, Jing-Jing; Feng, Shu-Dan; Zhang, Zun-Jian; Chen, Yun

Arzneimittel-Forschung/Drug Research, 2008 , vol. 58, # 10 p. 497 - 500 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

apoptosis; inhibition of

Species or TestSystem (Pharmacological Data)

Wistar rat cultured astrocytes

Concentration (Pharmacological Data)

0.1 - 10 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO and diluted in medium giving final conc. not exceeding 0.05 percent DMSO

Method (Pharmacological Data)

cells maintained for 8 h in simulated ischemic conditions (37 deg C, 5 percent CO2, 3 percent O2) in the presence of title comp.; apoptosis evaluated by Hoechst staining, fluorescence microscopy

Further Details (Pharmacological Data)

control: without title comp., normoxic conditions; further investigation on mechanism of action using extracellular regulated kinase 1 and 2 (Erk1/2) inhibitor U0126 or phosphatidylinositol 3-kinase/Akt (PI3-K/Akt) inhibitor wortmannin

Results

title comp. dose-dependently protected cells from ischemia-induced apoptosis (diagram, photo); at 10 μmol/l title comp. dose, 11 percent apoptosis of control ischemic cells observed; the effect involves both Erk1/2 and PI3-K/Akt pathways

Reference

Gabryel, Bozena; Pudelko, Anna; Malecki, Andrzej

European Journal of Pharmacology, 2004 , vol. 494, # 2-3 p. 111 - 120 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cytoprotective

Species or TestSystem (Pharmacological Data)

Wistar rat cultured astrocytes

Concentration (Pharmacological Data)

0.1 - 10 μmol/l

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Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO and diluted in medium giving final conc. not exceeding 0.05 percent DMSO

Method (Pharmacological Data)

cells maintained for 8 h in simulated ischemic conditions (37 deg C, 5 percent CO2, 3 percent O2) in the presence of title comp.; cell viability determined by MTT conversion assay

Further Details (Pharmacological Data)

Results

title comp. significantly increased cell viability at 1 and 10 μmol/l (diagram); the effect involves Erk1/2 but not PI3-K/Akt pathway

Reference

Gabryel, Bozena; Pudelko, Anna; Malecki, Andrzej

European Journal of Pharmacology, 2004 , vol. 494, # 2-3 p. 111 - 120 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cytoprotective

Species or TestSystem (Pharmacological Data)

Wistar rat cultured astrocytes

Concentration (Pharmacological Data)

0.1 - 10 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO and diluted in medium giving final conc. not exceeding 0.05 percent DMSO

Method (Pharmacological Data)

cells maintained for 8 h in simulated ischemic conditions (37 deg C, 5 percent CO2, 3 percent O2) in the presence of title comp.; LDH release measured by spectrometry

Further Details (Pharmacological Data)

Results

title comp. dose-dependently reduced LDH release (diagram); the effect involves both Erk1/2 and PI3-K/Akt pathways

Reference

Gabryel, Bozena; Pudelko, Anna; Malecki, Andrzej

European Journal of Pharmacology, 2004 , vol. 494, # 2-3 p. 111 - 120 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

expression of Erk1/2 kinases; induction of

Species or TestSystem (Pharmacological Data)

Wistar rat cultured astrocytes

Concentration (Pharmacological Data)

0.1 - 10 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO and diluted in medium giving final conc. not exceeding 0.05 percent DMSO

Method (Pharmacological Data)

cells maintained for 8 h in simulated ischemic conditions (37 deg C, 5 percent CO2, 3 percent O2) in the presence of title comp.; expression of Erk1/2 kinases measured by Western blot

Further Details (Pharmacological Data)

control: without title comp., normoxic conditions; Erk1/2: extracellular regulated kinase 1 and 2; reference: U0126

Results

title comp. significantly stimulated the expression of Erk1/2 kinases (5 - 6-fold at 10 μmol/l) (diagram)

Reference

Gabryel, Bozena; Pudelko, Anna; Malecki, Andrzej

European Journal of Pharmacology, 2004 , vol. 494, # 2-3 p. 111 - 120 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

expression of Akt kinase; induction of

Species or TestSystem

Wistar rat cultured astrocytes

(Pharmacological Data)

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Concentration (Pharmacological Data)

0.1 - 10 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO and diluted in medium giving final conc. not exceeding 0.05 percent DMSO

Method (Pharmacological Data)

cells maintained for 8 h in simulated ischemic conditions (37 deg C, 5 percent CO2, 3 percent O2) in the presence of title comp.; expression of Akt kinase measured by Western blot

Further Details (Pharmacological Data)

control: without title comp., normoxic conditions; reference: wortmannin

Results

title comp. significantly stimulated the expression of Akt kinase (180 percent of control at 10 μmol/l) (diagram)

Reference

Gabryel, Bozena; Pudelko, Anna; Malecki, Andrzej

European Journal of Pharmacology, 2004 , vol. 494, # 2-3 p. 111 - 120 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

D-glucose transport; inhibition of

Species or TestSystem (Pharmacological Data)

human erythrocytes

Method (Pharmacological Data)

cells pretreated with 100 mmol/l of D-glucose solution, incubated for 2 h, centrifuged, thick cell suspn. was added to a saline soln. containing title comp., vigorously stirred; glucose exit was monitored photometrically as a change in light scattering

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

1.05 nmol/l

Reference

Naftalin, Richard J.; Cunningham, Philip; Afzal-Ahmed, Iram

British Journal of Pharmacology, 2004 , vol. 142, # 3 p. 594 - 608 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transport

Species or TestSystem (Pharmacological Data)

human erythrocytes

Method (Pharmacological Data)

cells pretreated with 100 mmol/l of D-glucose solution, incubated for 2 h, centrifuged, thick cell suspn. was added to a saline soln. containing title comp. and PB (0.91 mmol/l); glucose exit was monitored photometrically as a change in light scattering

Further Details (Pharmacological Data)

PB: sodium pentobarbital

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

0.24 mmol/l

Results

title comp. antagonized pentobarbital-dependent inhibition of human erythrocyte D-glucose transport

Reference

Naftalin, Richard J.; Cunningham, Philip; Afzal-Ahmed, Iram

British Journal of Pharmacology, 2004 , vol. 142, # 3 p. 594 - 608 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

behavioural symptoms

Species or TestSystem

Sprague-Dawley rat

(Pharmacological Data)

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Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

15 mg/kg

Kind of Dosing (Pharmacological Data)

once a day; dissolved in 25 percent solution of 2-hydroxypropyl-β-cyclodextrin in normal saline

Method (Pharmacological Data)

submissive behavior model; submissive rats injected with title comp., while dominant rats injected with vehicle; treatment performed for 3 to 4 weeks; reduction of submissive behavior model measured

Further Details (Pharmacological Data)

dominance level value defined as difference in feeding scores between dominant and submissive rats of pair

Results

title comp. decreased dominance level that became sign. after 2nd week of treatment; effect appeared to diminish during 3rd week, vs. in control during 2nd week

Reference

Knapp, Richard J; Goldenberg, Rachel; Shuck, Caroline; Cecil, Alicia; Watkins, Jeff; Miller, Cortland; Crites, Glenda; Malatynska, Ewa

European Journal of Pharmacology, 2002 , vol. 440, # 1 p. 27 - 35 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

agonist

Species or TestSystem (Pharmacological Data)

cerebellar Purkinje neurons

Concentration (Pharmacological Data)

100 - 1000 μmol/l

Kind of Dosing (Pharmacological Data)

applied by bath perfusion

Method (Pharmacological Data)

in vitro; potentiation of AMPA receptor-mediated inward currents in acutely isolated cells determined; cells voltage-clamped at -70 mV; 100 μmol/l glutamate-evoked inward currents; extracellular solution, pH 7.4; intracellular solution, pH 7.15

Further Details (Pharmacological Data)

room temp.; AMPA: α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid

Results

title comp. produced conc.-dependent increases in AMPA receptor-mediated inward currents (graphical representation)

Reference

Zarrinmayeh; Bleakman; Gates; Yu; Zimmerman; Ornstein; McKennon; Arnold; Wheeler; Skolnick

Journal of medicinal chemistry, 2001 , vol. 44, # 3 p. 302 - 304 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

metabolic

Species or TestSystem (Pharmacological Data)

sponteneously hypertensive rat

Route of Application

peroral

Concentration (Pharmacological Data)

10 - 30 mg/kg

Kind of Dosing (Pharmacological Data)

administered 1 h after operation; dissolved in water

Method (Pharmacological Data)

in vivo; effect on cerebral energy metabolism tested; 5 or 6 rats (340-410 g)/dose exhibiting cerebral ischemia induced by bilateral common carotid artery ligation; irradiated with microwaves 4 h after dosing; cortex portions of each brain isolated

Further Details (Pharmacological

levels of ATP, lactate, and pyruvate determined by ATP, lactate, and pyruvate tests, respectively; 3 and 10 mg/kg doses used; control: saline-treated rats

Data)

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Results

title comp. caused slight increase in conc. of ATP and slight decrease in lactate/pyruvate ratio

Reference

Oka; Matsumoto; Hirooka; Suzuki

Chemical and Pharmaceutical Bulletin, 2000 , vol. 48, # 8 p. 1121 - 1124 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

pharmacokinetics

Species or TestSystem (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

intravenous

Concentration (Pharmacological Data)

30 mg/kg

Kind of Dosing (Pharmacological Data)

through cannula as a solution (0.15ml/100g) in a mixture of propylene glycol-ethanol-water (5:2:3, v/v)

Method (Pharmacological Data)

rats (220-250g) used; detection of title comp. (AP) and its metabolites (ABA, PD and AA) by HPLC

Further Details (Pharmacological Data)

ABA=4-p-anisamidobutyric acid; PD=2-pyrrolidinone; AA=p-anisic acid; C=cerebral cortex; H=hippocampus; T=thalamus; AUC0-2(μg h/g)=area under concentration-time curve over 2 h; MRT(h)=mean residence time; ke(1/h)=elimination rate constant

Results

AUC0-2 for AP/AA/PD in C, H and T 0.145/1.91/9.15, 0.102/1.92/8.98 and 0.134/1.79/9.28; MRT: 0.47/0.71/1.00, 0.48/0.68/0.99 and 0.39/0.68/1.03; ke: 5.80/1.62/0.235, 6.01/1.81/0.273 and 6.27/1.77/0.162; conc. of ABA was below detection limit (10 ng/g)

Reference

Ogiso, Taro; Uchiyama, Kaori; Suzuki, Hiroko; Yoshimoto, Mika; Tanino, Tadatoshi; Iwaki, Masahiro; Satoshi, Uno

Biological and Pharmaceutical Bulletin, 2000 , vol. 23, # 4 p. 482 - 486 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

pharmacokinetics

Species or TestSystem (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

peroral

Concentration (Pharmacological Data)

50 mg/kg

Kind of Dosing (Pharmacological Data)

aqueous suspension (0.5ml/100g) in 1.5 percent carboxy methyl cellulose

Method (Pharmacological Data)

rats (220-250g) used; detection of title comp. (AP) and its metabolites (ABA, PD and AA) by HPLC

Further Details (Pharmacological Data)

ABA=4-p-anisamidobutyric acid; PD=2-pyrrolidinone; AA=p-anisic acid; C=cerebral cortex; H=hippocampus; T=thalamus; AUC0-4(μg h/g)=area under concentration-time curve over 4 h; MRT(h)=mean residence time; F( percent)=apparent bioavailability

Results

AUC0-4 for AP/AA/PD in C, H and T 0.177/3.371/1.674, 0.215/3.357/1.567 and 0.188/3.157/1.594; MRT: 1.25/0.93/1.02, 1.24/0.90/1.00 and 1.32/0.90/0.96; F: 0.10 in C, 0.12 in H and 0.10 in T; concentration of ABA was below detection limit (10 ng/g)

Reference

Ogiso, Taro; Uchiyama, Kaori; Suzuki, Hiroko; Yoshimoto, Mika; Tanino, Tadatoshi; Iwaki, Masahiro; Satoshi, Uno

Biological and Pharmaceutical Bulletin, 2000 , vol. 23, # 4 p. 482 - 486 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

behavioural symptoms

Species or TestSystem

Wistar rat

(Pharmacological Data)

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Sex

male

Route of Application

peroral

Concentration (Pharmacological Data)

10 - 100 mg/kg

Kind of Dosing (Pharmacological Data)

title comp. suspended in carboxymethylcellulose solution containing Triton X-100

Method (Pharmacological Data)

rats aged 8 - 9 months; title comp. administered 0.5 h before 8-OH-DPAT/saline; 0.5 h after 8-OH-DPAT/saline injection behavioral testing performed; choice reaction time (CRT), percent Correct, percent Omission and task-associated motor activity measurement

Further Details (Pharmacological Data)

reference comp.: nefiracetam; 8-OH-DPAT: 8-hydroxy-2-(di-n-propylamino)tetralin; percent Correct: percentage of total trials in which task performed correctly; percent Omission: percentage of total trials in which no response made

Results

8-OH-DPAT: title comp. sign. reduced CRT (30 mg/kg), increased percent Correct (10, 30 mg/kg) and decreased percent Omission (30, 100 mg/kg); saline: no effect (figure, table)

Reference

Nakamura, Kazuo; Kurasawa, Mitsue

Naunyn-Schmiedeberg's Archives of Pharmacology, 2000 , vol. 361, # 5 p. 521 - 528 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

behavioural symptoms

Species or TestSystem (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

peroral

Concentration (Pharmacological Data)

3 - 30 mg/kg

Kind of Dosing (Pharmacological Data)

title comp. suspended in carboxymethylcellulose solution containing Triton X-100

Method (Pharmacological Data)

rats aged 8 - 9 months; title comp. administered with DOI/saline; 2 h later behavioral testing performed; choice reaction time (CRT) and motor activity measurement

Further Details (Pharmacological Data)

reference comp.: nefiracetam; DOI: 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane

Results

DOI: title comp. sign. reduced CRT (10 mg/kg) (figure); saline: no effect

Reference

Nakamura, Kazuo; Kurasawa, Mitsue

Naunyn-Schmiedeberg's Archives of Pharmacology, 2000 , vol. 361, # 5 p. 521 - 528 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

behavioural symptoms

Species or TestSystem (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

peroral

Concentration (Pharmacological Data)

10 - 100 mg/kg

Kind of Dosing (Pharmacological Data)

title comp. suspended in carboxymethylcellulose solution containing Triton X-100

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Method (Pharmacological Data)

rats aged 8-9 months; title comp. administered 0.5 h before 8-OH-DPAT/saline; 5-HT syndrome evaluated

Further Details (Pharmacological Data)

8-OH-DPAT: 8-hydroxy-2-(di-n-propylamino)tetralin

Results

title comp. reduced increased urination and defecation

Reference

Nakamura, Kazuo; Kurasawa, Mitsue

Naunyn-Schmiedeberg's Archives of Pharmacology, 2000 , vol. 361, # 5 p. 521 - 528 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

neuroregulatoric

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat

Sex

female

Route of Application

intracerebroventricular

Concentration (Pharmacological Data)

0.025 - 2.5 μg

Kind of Dosing (Pharmacological Data)

title comp. was dissolved in distilled water and diluted with artificial cerebrospinal fluid

Method (Pharmacological Data)

after title comp. administration to rats with left MCA occlusion bladder overactivity evaluated for up to 120 min using cystometrography (bladder capacity, bladder contraction pressure, micturition threshold pressure determined)

Further Details (Pharmacological Data)

MCA: middle cerebral artery

Results

title comp. increased bladder capacity (98.4 and 122.4 percent at 0.025 and 2.5 μg/rat, resp.) but did not affect bladder contraction pressure and micturition threshold pressure (figure, table)

Reference

Nakada, Yasushi; Yokoyama, Osamu; Komatsu, Kazuto; Kodama, Koichi; Yotsuyanagi, Satoshi; Niikura, Susumu; Nagasaka, Yasuhiro; Namiki, Mikio

Journal of Pharmacology and Experimental Therapeutics, 2000 , vol. 293, # 3 p. 921 - 928 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

neuroregulatoric

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat

Sex

female

Route of Application

intracerebroventricular

Concentration (Pharmacological Data)

0.025 - 2.5 μg

Kind of Dosing (Pharmacological Data)

title comp. was dissolved in distilled water and diluted with artificial cerebrospinal fluid

Method (Pharmacological Data)

after title comp. administration to sham-operated rats bladder overactivity evaluated for up to 120 min using cystometrography (bladder capacity, bladder contraction pressure, micturition threshold pressure determined)

Further Details (Pharmacological Data)

MCA: middle cerebral artery

Comment (Pharmacological Data)

No effect

Reference

Nakada, Yasushi; Yokoyama, Osamu; Komatsu, Kazuto; Kodama, Koichi; Yotsuyanagi, Satoshi; Niikura, Susumu; Nagasaka, Yasuhiro; Namiki, Mikio

Journal of Pharmacology and Experimental Therapeutics, 2000 , vol. 293, # 3 p. 921 - 928

Title/Abstract Full Text View citing articles Show Details

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Effect (Pharmacological Data)

neuroregulatoric

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat

Sex

female

Route of Application

peroral

Concentration (Pharmacological Data)

30 - 300 mg/kg

Kind of Dosing (Pharmacological Data)

title comp. was suspended in 0.5 percent methylcellulose solution

Method (Pharmacological Data)

Further Details (Pharmacological Data)

MCA: middle cerebral artery

Results

title comp. increased bladder capacity (34.3 and 40.9 percent at 100 and 300 mg/kg, resp.) but did not affect bladder contraction pressure and micturition threshold pressure (figure)

Reference

Nakada, Yasushi; Yokoyama, Osamu; Komatsu, Kazuto; Kodama, Koichi; Yotsuyanagi, Satoshi; Niikura, Susumu; Nagasaka, Yasuhiro; Namiki, Mikio

Journal of Pharmacology and Experimental Therapeutics, 2000 , vol. 293, # 3 p. 921 - 928 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

neuroregulatoric

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat

Sex

female

Route of Application

peroral

Concentration (Pharmacological Data)

30 - 300 mg/kg

Kind of Dosing (Pharmacological Data)

title comp. was suspended in 0.5 percent methylcellulose solution

Method (Pharmacological Data)

Further Details (Pharmacological Data)

MCA: middle cerebral artery

Comment (Pharmacological Data)

No effect

Reference

Nakada, Yasushi; Yokoyama, Osamu; Komatsu, Kazuto; Kodama, Koichi; Yotsuyanagi, Satoshi; Niikura, Susumu; Nagasaka, Yasuhiro; Namiki, Mikio

Journal of Pharmacology and Experimental Therapeutics, 2000 , vol. 293, # 3 p. 921 - 928 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

neuroregulatoric

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat

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Sex

female

Route of Application

peroral

Concentration (Pharmacological Data)

100 mg/kg

Kind of Dosing (Pharmacological Data)

title comp. was suspended in 0.5 percent methylcellulose solution

Method (Pharmacological Data)

after title comp. and ATR administration to rats with left MCA occlusion bladder overactivity evaluated for up to 120 min using cystometrography (bladder capacity, bladder contraction pressure, micturition threshold pressure determined)

Further Details (Pharmacological Data)

MCA: middle cerebral artery; ATR: atropine (1 μg/rat, i.c.v., 10 min after title comp. administration)

Results

title comp.-induced increase in bladder capacity was completely inhibited by atropine (figure)

Reference

Nakada, Yasushi; Yokoyama, Osamu; Komatsu, Kazuto; Kodama, Koichi; Yotsuyanagi, Satoshi; Niikura, Susumu; Nagasaka, Yasuhiro; Namiki, Mikio

Journal of Pharmacology and Experimental Therapeutics, 2000 , vol. 293, # 3 p. 921 - 928 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

neuroprotective

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat

Sex

female

Route of Application

peroral

Concentration (Pharmacological Data)

30 - 300 mg/kg

Kind of Dosing (Pharmacological Data)

title comp. was suspended in 0.5 percent methylcellulose solution

Method (Pharmacological Data)

after title comp. administration with/without ATR to rats with left MCA occlusion brain removed; area of ischemic lesion in cerebral cortex and striatum determined

Further Details (Pharmacological Data)

MCA: middle cerebral artery; ATR: atropine (1 μg/rat, i.c.v., 10 min after title comp. administration)

Comment (Pharmacological Data)

No effect

Reference

Nakada, Yasushi; Yokoyama, Osamu; Komatsu, Kazuto; Kodama, Koichi; Yotsuyanagi, Satoshi; Niikura, Susumu; Nagasaka, Yasuhiro; Namiki, Mikio

Journal of Pharmacology and Experimental Therapeutics, 2000 , vol. 293, # 3 p. 921 - 928 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

neuroprotective

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat

Sex

female

Route of Application

intracerebroventricular

Concentration (Pharmacological Data)

0.025 - 2.5 μg

Kind of Dosing (Pharmacological Data)

title comp. was dissolved in distilled water and diluted with artificial cerebrospinal fluid

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Method (Pharmacological Data)

after title comp. administration to rats with left MCA occlusion brain removed; area of ischemic lesion in cerebral cortex and striatum determined

Further Details (Pharmacological Data)

MCA: middle cerebral artery

Comment (Pharmacological Data)

No effect

Reference

Nakada, Yasushi; Yokoyama, Osamu; Komatsu, Kazuto; Kodama, Koichi; Yotsuyanagi, Satoshi; Niikura, Susumu; Nagasaka, Yasuhiro; Namiki, Mikio

Journal of Pharmacology and Experimental Therapeutics, 2000 , vol. 293, # 3 p. 921 - 928 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat hippocampal slice

Sex

male

Concentration (Pharmacological Data)

1 - 100 μmol/l

Kind of Dosing (Pharmacological Data)

in conc. 100 μmol/l stock solution was prepared in DMSO; in remaining experiments stock solution was prepared in ethanol:water (1:10); then solutions were diluted in saline

Method (Pharmacological Data)

slices were labeled with <3H>NA and perfused with Mg(+2)-containing solution at 37 deg C; title comp. was added with KYNA (1 mmol/l) at t=30 min; AMPA (100 μmol/l) was added at t=73 min; <3H>NA determined by tritium release from superfusate fractions

Further Details (Pharmacological Data)

control: without title comp.; NA: noradrenaline; KYNA: kynurenic acid; AMPA: α-amino-3-hydroxy-5-methylisoxazole-4-propionic acid

Comment (Pharmacological Data)

No effect

Reference

Pittaluga, Anna; Bonfanti, Andrea; Arvigo, Daniela; Raiteri, Maurizio

Naunyn-Schmiedeberg's Archives of Pharmacology, 1999 , vol. 359, # 4 p. 272 - 279 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat hippocampal slice

Sex

male

Concentration (Pharmacological Data)

0.01 - 1 μmol/l

Kind of Dosing (Pharmacological Data)

stock solution (10 mmol/l) was dissolved in ethanol/water 1:10 and then diluted in saline

Method (Pharmacological Data)

slices were labeled with <3H>NA and perfused with Mg(+2)-free solution at 37 deg C; title comp. was added with kynurenic acid (100 μmol/l) at t=30 min; NMDA was added at t=73 min; <3H>NA determined by tritium release from superfusate fractions

Further Details (Pharmacological Data)

control: without title comp.; NA: noradrenaline; NMDA: N-methyl-D-aspartate

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

0.1 μmol/l

Results

title comp. in concentration-dependent manner attenuated the kynurenic acid antagonism to NMDA-stimulated release of <3H>NA

(diagram); effect was almost complete at 1 μmol/l

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Reference

Pittaluga, Anna; Bonfanti, Andrea; Arvigo, Daniela; Raiteri, Maurizio

Naunyn-Schmiedeberg's Archives of Pharmacology, 1999 , vol. 359, # 4 p. 272 - 279 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat hippocampal slice

Sex

male

Concentration (Pharmacological Data)

1 - 10 μmol/l

Kind of Dosing (Pharmacological Data)

stock solution (10 mmol/l) was dissolved in ethanol/water 1:10; then diluted in saline

Method (Pharmacological Data)

slices were labeled with <3H>NA and perfused with Mg(+2)-free solution at 37 deg C; title comp. was added with NMDA at t=73 min until the end of superfusion; <3H>NA was determined by tritium release from supefusate fractions

Further Details (Pharmacological Data)

control: without title comp.; NA: noradrenaline; NMDA: N-methyl-D-aspartate

Comment (Pharmacological Data)

No effect

Reference

Pittaluga, Anna; Bonfanti, Andrea; Arvigo, Daniela; Raiteri, Maurizio

Naunyn-Schmiedeberg's Archives of Pharmacology, 1999 , vol. 359, # 4 p. 272 - 279 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat hippocampal slice

Sex

male

Concentration (Pharmacological Data)

10 - 100 μmol/l

Kind of Dosing (Pharmacological Data)

in experiments with 100 μmol/l stock solution (100 mmol/l) was prepared in DMSO, in others stock solution (10 mmol/l) was dissolved in ethanol/water 1:10; then diluted in saline

Method (Pharmacological Data)

slices were labeled with <3H>NA and perfused with Mg(+2)-containing solution at 37 deg C; title comp. was added together AMPA at t = 73 min until the end of superfusion; <3H>NA determined by tritium release from superfusate fractions

Further Details (Pharmacological Data)

control: without title comp.; NA: noradrenaline; AMPA: α-amino-3-hydroxy-5-methylisoxazole-4-propionic acid

Results

title comp. at conc. 100 μmol/l stimulated <3H>NA outflow (table)

Reference

Pittaluga, Anna; Bonfanti, Andrea; Arvigo, Daniela; Raiteri, Maurizio

Naunyn-Schmiedeberg's Archives of Pharmacology, 1999 , vol. 359, # 4 p. 272 - 279 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat hippocampal synaptosomes

Sex

male

Concentration (Pharmacological Data)

10 - 100 μmol/l

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Kind of Dosing (Pharmacological Data)

in experiments with 100 μmol/l stock solution (100 mmol/l) was prepared in DMSO, in others stock solution (10 mmol/l) was dissolved in ethanol/water 1:10; then diluted in saline

Method (Pharmacological Data)

synaptosomes were labeled with <3H>NA and perfused with Mg(+2)-containing solution at 37 deg C; title comp. was added with AMPA (100 μmol/l); <3H>NA was determined by tritium release from superfusate fractions

Further Details (Pharmacological Data)

control: without title comp.; NA: noradrenaline; AMPA: α-amino-3-hydroxy-5-methylisoxazole-4-propionic acid

Results

title comp. at conc. 100 μmol/l stimulated <3H>NA outflow (table)

Reference

Pittaluga, Anna; Bonfanti, Andrea; Arvigo, Daniela; Raiteri, Maurizio

Naunyn-Schmiedeberg's Archives of Pharmacology, 1999 , vol. 359, # 4 p. 272 - 279 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat hippocampal synaptosomes

Sex

male

Concentration (Pharmacological Data)

10 - 100 μmol/l

Kind of Dosing (Pharmacological Data)

in experiments with 100 μmol/l stock solution (100 mmol/l) was prepared in DMSO, in others stock solution (10 mmol/l) was dissolved in ethanol/water 1:10; then diluted in saline

Method (Pharmacological Data)

synaptosomes were labeled with <3H>NA and perfused with Mg(+2)-free solution at 37 deg C; title comp. was added with NMDA (100 μmol/l); <3H>NA was determined by tritium release from supefusate fractions

Further Details (Pharmacological Data)

control: without title comp.; NA: noradrenaline; NMDA: N-methyl-D-aspartate

Comment (Pharmacological Data)

No effect

Reference

Pittaluga, Anna; Bonfanti, Andrea; Arvigo, Daniela; Raiteri, Maurizio

Naunyn-Schmiedeberg's Archives of Pharmacology, 1999 , vol. 359, # 4 p. 272 - 279 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat hippocampal slice

Sex

male

Concentration (Pharmacological Data)

0.01 - 1 μmol/l

Kind of Dosing (Pharmacological Data)

stock solution (10 mmol/l) was dissolved in ethanol/water 1:10 and then diluted in saline

Method (Pharmacological Data)

slices labeled with <3H>NA were perfused with Mg(+2)-free solution at 37 deg C; title comp. was added; <3H>NA was determined by tritium release from superfusate fractions

Further Details (Pharmacological Data)

control: without title comp.; NA: noradrenaline

Comment (Pharmacological Data)

No effect

Reference

Pittaluga, Anna; Bonfanti, Andrea; Arvigo, Daniela; Raiteri, Maurizio

Naunyn-Schmiedeberg's Archives of Pharmacology, 1999 , vol. 359, # 4 p. 272 - 279 Title/Abstract Full Text View citing articles Show Details

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Effect (Pharmacological Data)

neuroregulatoric

Species or TestSystem (Pharmacological Data)

human cortex slice

Sex

male and female

Concentration (Pharmacological Data)

10 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in EtOH+water and diluted in medium

Method (Pharmacological Data)

parts of frontal, temporal lobes; NMDA receptors tested; labeling with <3H>NE; superfusion with Mg(2+)-free medium (ca. 100 min); title comp. added at 73 min or title comp./NMDA added at 45/73 min of superfusion; chromatography, scintillation counting

Further Details (Pharmacological Data)

incubation medium contained selective serotonin uptake inhibitor and selective dopaminergic uptake inhibitor; NMDA: N-methyl-Daspartate; NE: norepinephrine

Comment (Pharmacological Data)

No effect

Reference

Pittaluga, Anna; Pattarini, Roberto; Andrioli, Gian Carlo; Viola, Concetta; Munari, Claudio; Raiteri, Maurizio

Journal of Pharmacology and Experimental Therapeutics, 1999 , vol. 290, # 1 p. 423 - 428 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

neuroregulatoric

Species or TestSystem (Pharmacological Data)

human cortex slice

Sex

male and female

Concentration (Pharmacological Data)

3 - 10 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in EtOH+water and diluted in medium

Method (Pharmacological Data)

parts of frontal, temporal lobes; NMDA receptors tested; labeling with <3H>NE; superfusion with Mg(2+)-free medium (ca. 100 min); title comp.+KYNA/NMDA added at 45/73 min of superfusion; chromatography, scintillation counting

Further Details (Pharmacological Data)

incubation medium contained selective serotonin uptake inhibitor and selective dopaminergic uptake inhibitor; NMDA: N-methyl-Daspartate; NE: norepinephrine; KYNA: kynurenate, 300 μmol/l

Results

title comp. (10 μmol/l) counteracted antagonism produced by kynurenate (figure)

Reference

Pittaluga, Anna; Pattarini, Roberto; Andrioli, Gian Carlo; Viola, Concetta; Munari, Claudio; Raiteri, Maurizio

Journal of Pharmacology and Experimental Therapeutics, 1999 , vol. 290, # 1 p. 423 - 428 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

effects on the magnitude of the current induced by AMPA ((R/S)-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid) and measured in Xenopus oocytes expressing rat cortex AMPA receptors

Reference

Journal of Medicinal Chemistry, 1998 , vol. 41, # 16 p. 2946 - 2959 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

effects on the duration of the postsynaptic excitatory potential induced by electric stimulation in rat hippocampal slices; in vivo study of the facilitation of the cerebral excitation induced by an auditory stress in DBA/2 mice

Reference

Journal of Medicinal Chemistry, 1998 , vol. 41, # 16 p. 2946 - 2959 Title/Abstract Full Text View citing articles Show Details

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Effect (Pharmacological Data)

pharmacokinetics

Species or TestSystem (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

intravenous

Concentration (Pharmacological Data)

30 mg/kg

Kind of Dosing (Pharmacological Data)

single dose; injected solution of title comp. in a mixture of propylene glycol:ethanol:water (5:2:3, v/v)

Exposure Period (Pharmacological Data)

6 h

Method (Pharmacological Data)

in vivo; 3-5 rats, 220-250 g; cannulated jugular vein; treated with title comp.; collected blood at various time points at 5 min - 6 h after dosing; measured plasma conc. of title comp. by HPLC

Further Details (Pharmacological Data)

calculated pharmacokinetic parameters using two-compartment model

Results

V1: 743.2 ml/kg; k10 8.83 h-1; k12: 0.84 h-1; k21: 2.44 h-1; A: 38.95 μg/ml; α: 9.94 h-1; B: 1.41 μg/ml; β: 2.16 h-1; AUC: 4.57 μg*h/ml;

AUMC: 0.69 μg*h2/ml; MRT: 0.15 h; Vss: 999.3 ml/kg

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Reference

Wu, X.Y.; Eshun, G.; Zhou, Y.

Journal of Pharmaceutical Sciences, 1998 , vol. 87, # 5 p. 594 - 598 Title/Abstract Full Text Show Details

Effect (Pharmacological Data)

pharmacokinetics

Species or TestSystem (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

peroral

Concentration (Pharmacological Data)

50 - 100 mg/kg

Kind of Dosing (Pharmacological Data)

single dose; received 50 and 100 mg/kg aq. suspension of a title comp. (0.5 ml/100g) in carboxymethylcellulose

Exposure Period (Pharmacological Data)

8 h

Method (Pharmacological Data)

in vivo; 3-5 rats, 220-250 g; cannulated jugular vein; treated with title comp.; collected blood at various time points at 20 min - 8 h after dosing; measured plasma conc. of title comp. by HPLC

Further Details (Pharmacological Data)

calculated pharmacokinetic parameters using two-compartment model

Results

AUC, μg*h/ml: 0.79 (50 mg/kg), 1.20 100 mg/kg); AUMC, μg*h2/ml: 0.88 (50 mg/kg), 3.10 (100 mg/kg); MRT, h: 1.11 (50 mg/kg), 1.92 (100 mg/kg); MAT, h: 0.99 (50 mg/kg), 1.79 (100 mg/kg); F (absol. bioavailability): 11.4 percent (50 mg/kg), 8.6 percent (100 mg/kg)

Reference

Wu, X.Y.; Eshun, G.; Zhou, Y.

Journal of Pharmaceutical Sciences, 1998 , vol. 87, # 5 p. 594 - 598 Title/Abstract Full Text Show Details

Effect (Pharmacological Data)

pharmacokinetics

Species or TestSystem

Wistar rat

(Pharmacological Data)

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Sex

male

Route of Application

intravenous

Concentration (Pharmacological Data)

30 mg/kg

Kind of Dosing (Pharmacological Data)

single dose; injected solution of title comp. in a mixture of propylene glycol:ethanol:water (5:2:3, v/v)

Exposure Period (Pharmacological Data)

6 h

Method (Pharmacological Data)

in vivo; 3-5 rats, 220-250 g; cannulated jugular vein; treated with title comp.; collected blood at various time points at 5 min - 6 h after dosing; measured plasma conc. of title comp. and its metabolites by HPLC

Further Details (Pharmacological Data)

calculated pharmacokinetic parameters using two-compartment model

Results

AUC: 4.15 μg*h/ml; AUMC: 0.529 μg*h2/ml; MRT: 0.13 h; Cl: 7440 ml/h/kg; Vss: 960 ml/kg

Reference

Wu, X.Y.; Eshun, G.; Zhou, Y.

Journal of Pharmaceutical Sciences, 1998 , vol. 87, # 5 p. 594 - 598 Title/Abstract Full Text Show Details

Comment (Pharmacological Data)

amnesia-reversal activity (electroconvulsive shock and scopolamine-induced amnesia in rats)

Reference

Mazurov, Anatoly A.; Andronati, Sergei A.; Korotenko, Tamara I.; Sokolenko, Nikolai I.; Dyadenko, Alexei I.; Shapiro, Yury E.; Gorbatyuk, Vitalii Ya.; Voronina, Tatyana A.

Bioorganic and Medicinal Chemistry, 1997 , vol. 5, # 11 p. 2029 - 2040 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

biotransformation

Species or TestSystem (Pharmacological Data)

human liver carboxylesterase (EC 3.1.1.1) pI 5.3

Method (Pharmacological Data)

in vitro; 0.1 M Tris-HCl buffer, pH 7.4; 37 deg C; monitoring of drug hydrolysis

Results

kinetic parameters of drug hydrolysis: to anisic acid: Km=0.085 mM and Vmax=0.009 μmol/mg protein/min; to anisamidobutyric acid: Km=0.095 and Vmax=0.007 μmol/mg protein/min

Reference

Takai, Satomi; Matsuda, Ayuka; Usami, Yoshiko; Adachi, Tetsuo; Sugiyama, Tadashi; Katagiri, Yoshihiro; Tatematsu, Masae; Hirano, Kazuyuki

Biological and Pharmaceutical Bulletin, 1997 , vol. 20, # 8 p. 869 - 873 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

biotransformation

Species or TestSystem (Pharmacological Data)

human liver carboxylesterase (EC 3.1.1.1) pI 4.5

Method (Pharmacological Data)

in vitro; 0.1 M Tris-HCl buffer, pH 7.4; 37 deg C; monitoring of drug hydrolysis

Results

kinetic parameters of drug hydrolysis: to anisic acid: Km=0.301 mM and Vmax=0.020 μmol/mg protein/min; to anisamidobutyric acid: Km=0.412 and Vmax=0.349 μmol/mg protein/min

Reference

Takai, Satomi; Matsuda, Ayuka; Usami, Yoshiko; Adachi, Tetsuo; Sugiyama, Tadashi; Katagiri, Yoshihiro; Tatematsu, Masae; Hirano, Kazuyuki

Biological and Pharmaceutical Bulletin, 1997 , vol. 20, # 8 p. 869 - 873 Title/Abstract Full Text View citing articles Show Details

Comment

ability to block the formation of cytotoxic hydroxyl radicals during ischaemia-reperfusion of mouse brain (male ddY mice)

(Pharmacological Data)

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Reference

Himori; Suzuki; Ueno

Journal of Pharmacy and Pharmacology, 1995 , vol. 47, # 3 p. 253 - 258 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

drug interaction

Species or TestSystem (Pharmacological Data)

adult Sprague Dawley rat hippocampal slices

Sex

male

Concentration (Pharmacological Data)

1 μmol/l

Kind of Dosing (Pharmacological Data)

1 ml/min

Exposure Period (Pharmacological Data)

50 min

Method (Pharmacological Data)

rat weight 200-250 g; decapitation, coronal slices from the ventro-medial hippocampus; 20 min labelled with 0.08 μM <3H>noradrenaline; superfusion; alone or together with 100 μM kynurenic acid added 45 min before 100 μM NMDA; radioactivity

Further Details (Pharmacological Data)

37 deg C; NMDA=N-methyl-D-aspartic acid

Results

complete recovery of the NMDA-induced <3H>noradrenaline release; alone no effect

Reference

Pittaluga, Anna; Pattarini, Roberto; Raiteri, Maurizio

European Journal of Pharmacology, 1995 , vol. 272, # 2/3 p. 203 - 210 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

HEK 293 cells

Concentration (Pharmacological Data)

1 mmol/l

Method (Pharmacological Data)

human embryonic kidney 293 (HEK 293) cells were grown at 37 deg C; transfected with cDNA to obtain heteromeric receptors conc. GluRAi/Bi, GluRA0/B0 and GluRBi/Di; perfused with rat Ringers'

Further Details (Pharmacological Data)

the title compound, 30 μM of cyclothiazide (CT) and 1 mM of L-glutamate in DMSO, by rapid application; platch-clamp electrophysiology recording at a holding potential of -60 mV

Results

slowed the desensitization, peak currents not additive in the presence of both potentiators

Reference

Johansen, Tina H.; Chaudhary, Archana; Verdoorn, Todd A.

Molecular Pharmacology, 1995 , vol. 48, # 5 p. 946 - 955 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

Xenopus oocytes

Concentration (Pharmacological Data)

2 - 5 mmol/l

Method (Pharmacological Data)

Ovaries from mature Xenopus laevis; defollicated, in modified Barth's saline for 2 h at RT; 1 ng cDNA inj. into the cucleus for exp. heteromeric combinations (GluRA, GluRD or GluRB cDNA); two-electrode voltage-clamp recording

Further Details (Pharmacological Data)

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L-glutamate (300 μM) in Ringers' solution, the title compound in the Ba2+-containing frog Ringers' solution in DMSO

Results

the magnitude of the potentiation much greater in flop receptors (Bo/Do than in flip receptors; Bi/Di)

Reference

Johansen, Tina H.; Chaudhary, Archana; Verdoorn, Todd A.

Molecular Pharmacology, 1995 , vol. 48, # 5 p. 946 - 955 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

neuroprotective

Species or TestSystem (Pharmacological Data)

rat hippocampus

Concentration (Pharmacological Data)

1 - 200 μmol/l

Exposure Period (Pharmacological Data)

90 min

Method (Pharmacological Data)

hippocampus of animals was cut, slices were incubated in oxygenated Krebs solution in presence of N-methyl-D-aspartate (NMDA) for 30 min, slices were washed and further incubated with or without title compound

Further Details (Pharmacological Data)

slices were fixed, dehydrated, stained with methylene blue and azur II and examined by light microscopy; percentage of cell survival was calculated by the ratio between living cells and total cell number

Results

title compound prevents the neurotoxic effect induced by NMDA; neuroprotection does not require preincubantion with title compound; maximal effective concentration of title compound was 10 μM

Reference

Pizzi; Consolandi; Memo; Spano

European Journal of Pharmacology, 1995 , vol. 275, # 3 p. 311 - 314 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

drug interaction

Species or TestSystem (Pharmacological Data)

rat forebrain

Concentration (Pharmacological Data)

0.1 - 1000 μmol/l

Method (Pharmacological Data)

forebrains homogenized; membrane separated; incubated in Hepes containing buffer with <3H>MK801 (MK) without/with 100 μM kynurenate (KYNA) to inhibit MK binding; title comp. added to buffer

Further Details (Pharmacological Data)

specific MK binding determined by liquid scintillation; title comp. effect on MK binding and its inhibition by KYNA studied

Results

MK binding unaffected; KYNA inhibitory effect markedly (88 percent) reduced

Reference

Hamelin; Lehmann

European Journal of Pharmacology, 1995 , vol. 281, # 3 p. R11-R13 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

anticonvulsant

Species or TestSystem (Pharmacological Data)

DBA mice

Sex

male and female

Route of Application

intraperitoneal

Method (Pharmacological Data)

mice (4-5 weeks, 14-22g), genetically soundsensitive, were administered by title comp., 30 min later placed in individual cages in soundattenuated cabinet; after 30 s, 90 dB, 10-20 Hz acoustic stimulus delivered for 30 s

Further Details

presence of tonic convulsions noted; percent protection afforded by each dose of drug

(Pharmacological Data) Type (Pharmacological Data) Value of Type (Pharmacological Data)

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> 3.0 mmol/kg

Reference

Noyer, Michel; Gillard, Michel; Matagne, Alain; Henichart, Jean-Pierre; Wuelfert, Ernst

European Journal of Pharmacology, 1995 , vol. 286, # 2 p. 137 - 146 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

Spraue-Dawley rat hippocampus

Sex

male

Concentration (Pharmacological Data)

1 mmol/l

Method (Pharmacological Data)

rats (200-300 g) killed by decapitation; hippocampal membranes incubated 120 min at 4 deg C in Tris-HCl cont. 8 nM <3H>levetiracetam and title comp.

Further Details (Pharmacological Data)

radioactivity determined by liquid scintillation

Type (Pharmacological Data)

pKi

Value of Type (Pharmacological Data)

3.0 dimensionless

Results

title comp. displayed low affinity

Reference

Noyer, Michel; Gillard, Michel; Matagne, Alain; Henichart, Jean-Pierre; Wuelfert, Ernst

European Journal of Pharmacology, 1995 , vol. 286, # 2 p. 137 - 146 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

antagonist

Species or TestSystem (Pharmacological Data)

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ED50

striata from rat

Concentration (Pharmacological Data)

0.1 mmol/l

Method (Pharmacological Data)

striata dissected from embryos of pregnant OFA rats; neurons incub. in Krebs phosphate buffer (pH 7.4; 37 deg C) with <3H>arachidonic acid (AA), then with title comp. (15 min); AA release determined by TLC of medium and liquid scintillation

Further Details (Pharmacological Data)

AA release stimulated with (0.1 mM AMPA or 0.1 mM domoic acid (D)) + 1 mM carbachol (C); title comp. effect on stimulated AA release studied (table)

Comment (Pharmacological Data)

No effect

Reference

Petitet; Blanchard; Doble

European Journal of Pharmacology - Molecular Pharmacology Section, 1995 , vol. 291, # 2 p. 143 - 151 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

agonist

Species or TestSystem

Sprague-Dawley rat hippocampal slices

(Pharmacological Data)

66 of 72

67 of 72

Sex

not specified

Concentration (Pharmacological Data)

1 mmol/l

Method (Pharmacological Data)

in vitro; effect on AMPA-activated current; tissue from 12-16 days old rats; placed in recording chamber in Ringer's solution bubbled with 95 percent O2-5 percent CO2; room temp; whole-cell current elicited by 50 μM L-glutamate and 5 μM dizocilpine added

Further Details (Pharmacological Data)

whole-cell current elicited by 50 μM L-glutamate in presence 5 μM dizocilpine recorded in voltage-clamp CA1 pyramidal neurons

Results

produced 244 percent potentiation of AMPA-activated current

Reference

Zivkovic; Thompson; Bertolino; Uzunov; DiBella; Costa; Guidotti

Journal of Pharmacology and Experimental Therapeutics, 1995 , vol. 272, # 1 p. 300 - 309 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

memory enhancer

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

peroral

Concentration (Pharmacological Data)

< 300 μmol/kg

Kind of Dosing (Pharmacological Data)

single dose by oral gavage 1 h before test

Method (Pharmacological Data)

in vivo; effect on scopolamine-induced water maze performance deficit assayed; rats (250-300 g) kept at 22 deg C and 55 percent rel. humidity on 12 h light/dark cycle; injected i.p. with 4.95 μol/kg scopolamine 15 min before test

Type (Pharmacological Data)

ED50

Value of Type (Pharmacological Data)

Ca. 228 μmol/kg

Results

reduced scopolamine-induced performance deficit in water maze test

Reference

Zivkovic; Thompson; Bertolino; Uzunov; DiBella; Costa; Guidotti

Journal of Pharmacology and Experimental Therapeutics, 1995 , vol. 272, # 1 p. 300 - 309 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

memory enhancer

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

peroral

Concentration (Pharmacological Data)

< 300 μmol/kg

Kind of Dosing (Pharmacological Data)

single dose by oral gavage 1 h before test

Method (Pharmacological Data)

in vivo; effect on alprazolam-induced water maze performance deficit assayed; rats (250-300 g) kept at 22 deg C and 55 percent rel. humidity on 12 h light/dark cycle; injected i.p. with 0.36 μol/kg alprazolam 15 min before test

68 of 72

69 of 72

70 of 72

Type (Pharmacological Data)

ED50

Value of Type (Pharmacological Data)

40 - 50 μmol/kg

Results

reduced alprazolam-induced performance deficit in water maze test

Reference

Zivkovic; Thompson; Bertolino; Uzunov; DiBella; Costa; Guidotti

Journal of Pharmacology and Experimental Therapeutics, 1995 , vol. 272, # 1 p. 300 - 309 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

memory enhancer

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

peroral

Concentration (Pharmacological Data)

114 μmol/kg

Kind of Dosing (Pharmacological Data)

single dose by oral gavage 1 h before first trial

Method (Pharmacological Data)

in vivo; rats weighing 250-300 g kept at 22 deg C and 55 percent rel. humidity on 12 h light/dark cycle; rats placed in center of maze that included 8 incorrect choices; test repeated for 4 consecutive times with 20-min intertrial interval

Results

title comp. improved performance in consecutive trials but not significantly

Reference

Zivkovic; Thompson; Bertolino; Uzunov; DiBella; Costa; Guidotti

Journal of Pharmacology and Experimental Therapeutics, 1995 , vol. 272, # 1 p. 300 - 309 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

memory enhancer

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

peroral

Concentration (Pharmacological Data)

300 μmol/kg

Kind of Dosing (Pharmacological Data)

single dose by oral gavage 1 h before test

Method (Pharmacological Data)

in vivo; rats weighing 250-300 g kept at 22 deg C and 55 percent rel. humidity on 12 h light/dark cycle; trained once a day for 2 consecutive days in water maze A; 30 min after title comp. administration exposed to maze A and after additional 30 min to maze B

Further Details (Pharmacological Data)

performance-enhancing effect determined on water maze test; water maze A included possibility of 4 incorrect choices; water maze B included possibility of 7 incorrect choices

Results

at dose of 300 μol/kg title comp. improved significantly performance in maze B but had no effect in maze A

Reference

Zivkovic; Thompson; Bertolino; Uzunov; DiBella; Costa; Guidotti

Journal of Pharmacology and Experimental Therapeutics, 1995 , vol. 272, # 1 p. 300 - 309 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

amnesia-reversal activity in the electroconvulsive shock (ECS)- and Scopolamine-induced amnesia in mice; ineffective on spontaneous activity and neurovegetative system

Reference

Angelucci, Luciano; Calvisi, Pina; Catini, Roberto; Cosentino, Ugo; Cozzolino, Roberto; et al.

Journal of Medicinal Chemistry, 1993 , vol. 36, # 11 p. 1511 - 1519

Title/Abstract Full Text View citing articles Show Details

71 of 72

72 of 72

Comment (Pharmacological Data)

antiamnestic activity against electroconvulsive shock induced amnesia (mouse, i.p.)

Reference

Cerri; Farina; Pinza; Banfi

Farmaco, 1991 , vol. 46, # 7-8 p. 959 - 966 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

protective effect on the CNS (500 mg/day, p.o., man), cerebrovascular insuffuciency effect

Reference

Foltyn; Luecker; Schnitker; Wetzelsberger

Arzneimittel-Forschung, 1983 , vol. 33, # 6 p. 865 - 867 Title/Abstract Full Text View citing articles Show Details

Ecotoxicology (7) 1 of 7

2 of 7

3 of 7

Effect (Ecotoxicology)

receptor; regulation of

Species or TestSystem (Ecotoxicology)

chick cochlear nucleus magnocellularis neuronal cells

Concentration (Ecotoxicology)

0.1 - 5 mmol/l

Method (Ecotoxicology)

neurons plated; pulses of 10 mmol/l glutamate, lasting 100 ms, applied in presence of varying conc. of title comp.; effect on AMPA (αamino-3-hydroxy-5-methyl-4-isoxazolepropionic acid) receptor desensitization (DS) determined

Further Details (Ecotoxicology)

glutamate applied along with 200 μmol/l DL-aminophosphonovaleric acid and 10 μmol/l 7-chlorokynurenic acid in Ringer's soln.; control performed; EC: exponential components; CP: component

Results

slower EC of receptor DS became dominant with increase in the conc. of title comp.; an additional CP of about 30 ms was prominent at the highest conc.; 3 EC (1-, 7- and 30-ms CP) became dominant at 1 mmol/l; extent of DS was ca. 90.2 percent; diagram, table

Reference

Lawrence, J. Josh; Brenowitz, Stephan; Trussell, Laurence O.

Molecular Pharmacology, 2003 , vol. 64, # 2 p. 269 - 278 Title/Abstract Full Text View citing articles Show Details

Effect (Ecotoxicology)

receptor; regulation of

Species or TestSystem (Ecotoxicology)

chick cochlear nucleus magnocellularis neuronal cells

Concentration (Ecotoxicology)

0.1 - 5 mmol/l

Method (Ecotoxicology)

Further Details (Ecotoxicology)

glutamate applied along with 200 μmol/l DL-aminophosphonovaleric acid and 10 μmol/l 7-chlorokynurenic acid in Ringer's soln.; control performed

Results

title comp. at 0.1 mmol/l doubled the time constant of deactivation, doubling yet again at 5 mmol/l; deactivation increased from 0.55 ms in control to 1.95 ms with 5 mmol/l title comp.; diagrams

Reference

Lawrence, J. Josh; Brenowitz, Stephan; Trussell, Laurence O.

Molecular Pharmacology, 2003 , vol. 64, # 2 p. 269 - 278 Title/Abstract Full Text View citing articles Show Details

Effect (Ecotoxicology)

receptor; regulation of

Species or TestSystem (Ecotoxicology)

chick cochlear nucleus magnocellularis neuronal cells

Concentration (Ecotoxicology)

0.1 - 5 mmol/l

Method (Ecotoxicology)

neurons plated; pulses of 10 mmol/l glutamate, lasting 100 ms, applied in presence of varying conc. of title comp.; AMPA (α-amino-3hydroxy-5-methyl-4-isoxazolepropionic acid) receptor desensitization time constants determined

Further Details (Ecotoxicology)

glutamate applied along with 200 μmol/l DL-aminophosphonovaleric acid and 10 μmol/l 7-chlorokynurenic acid in Ringer's soln.; control performed

Results

title comp. at 0.1 mmol/l doubled the time constant of desensitization; time constant was 5- and 10-fold longer in 1 and 5 mmol/l title comp. treated group, resp.; desensitization slowed from 1.7 ms in control to 21.2 ms in 5 mmol/l title comp.; diagram

Reference

Lawrence, J. Josh; Brenowitz, Stephan; Trussell, Laurence O.

Molecular Pharmacology, 2003 , vol. 64, # 2 p. 269 - 278

Title/Abstract Full Text View citing articles Show Details

4 of 7

5 of 7

6 of 7

7 of 7

Effect (Ecotoxicology)

receptor; regulation of

Species or TestSystem (Ecotoxicology)

chick cochlear nucleus magnocellularis neuronal cells

Concentration (Ecotoxicology)

3 - 5 mmol/l

Method (Ecotoxicology)

paired-pulse desensitization; two pulses of 10 mmol/l glutamate (GM) applied, with the pulses separated by 10 ms and the duration of the first pulse (P1) increased with each repetition of the pair; effect of title comp. on channel-closing rate assessed

Further Details (Ecotoxicology)

control performed; DS: desensitization; NR: normalized response; IA: initial application; P2: second pulse

Results

in presence of title comp. (3 or 5 mmol/l), much less DS was apparent even for the briefest IA of GM; amplitude of response to P1 increased by 31 percent and 37 percent at 3 and 5 mmol/l, resp.; NR to P2 was 0.84 and 0.78 for short and long pulses, resp.; diagram

Reference

Lawrence, J. Josh; Brenowitz, Stephan; Trussell, Laurence O.

Molecular Pharmacology, 2003 , vol. 64, # 2 p. 269 - 278 Title/Abstract Full Text View citing articles Show Details

Effect (Ecotoxicology)

receptor; regulation of

Species or TestSystem (Ecotoxicology)

chick cochlear nucleus magnocellularis neuronal cells

Concentration (Ecotoxicology)

5 mmol/l

Method (Ecotoxicology)

20-ms conditioning pulse of glutamate followed by 1-ms test pulses applied at timed intervals; recovery after desensitizing pulses of glutamate measured in presence of title comp.

Further Details (Ecotoxicology)

control performed; title comp. effect determined to find whether microscopic rates of recovery from desensitization were sensitive to title comp.

Comment (Ecotoxicology)

No effect

Reference

Lawrence, J. Josh; Brenowitz, Stephan; Trussell, Laurence O.

Molecular Pharmacology, 2003 , vol. 64, # 2 p. 269 - 278 Title/Abstract Full Text View citing articles Show Details

Effect (Ecotoxicology)

deactivation of kainate current; prolonging

Species or TestSystem (Ecotoxicology)

chick cochlear nucleus magnocellularis neuronal cells

Concentration (Ecotoxicology)

5 mmol/l

Method (Ecotoxicology)

kainate currents in deactivation phase, peak amplitude, and desensitization or deactivation time constants measured in presence of title comp.

Further Details (Ecotoxicology)

control performed

Comment (Ecotoxicology)

No effect

Reference

Lawrence, J. Josh; Brenowitz, Stephan; Trussell, Laurence O.

Molecular Pharmacology, 2003 , vol. 64, # 2 p. 269 - 278 Title/Abstract Full Text View citing articles Show Details

Effect (Ecotoxicology)

deactivation of kainate current; prolonging

Species or TestSystem (Ecotoxicology)

chick cochlear nucleus magnocellularis neuronal cells

Concentration (Ecotoxicology)

5 mmol/l

Method (Ecotoxicology)

steady-state amplitude in deactivation of kainate current measured in presence of title comp.

Further Details (Ecotoxicology)

control performed small, but signif. enhancement of steady-state current was detected; diagram

Results Reference

Lawrence, J. Josh; Brenowitz, Stephan; Trussell, Laurence O.

Molecular Pharmacology, 2003 , vol. 64, # 2 p. 269 - 278 Title/Abstract Full Text View citing articles Show Details

Use/Application Use (61) Use Pattern

Reference

age-related cognitive decline

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schizophrenia

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positive AMPA receptor modulator; cognitive enhancer

NeuroSearch A/S

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NeuroSearch A/S

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memory impairment associated with depresssion

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traumatic brain injury (TBI)

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Cha, Albert

Patent: US2006/241144 A1, 2006 ; Title/Abstract Full Text Show Details

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Patent: US2006/63707 A1, 2006 ;

positive modulator of α-amino-3-hydroxy-5-methylisoxazolepropionic acid (AMPA) receptor

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Cha, Albert

Patent: US2006/241144 A1, 2006 ;

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Use Pattern frontal-subcortical dysfunction

Location

Reference Cha, Albert

Patent: US2006/241144 A1, 2006 ; Title/Abstract Full Text Show Details

traumatic brain injury

Cha, Albert

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depression

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chronic hepatitis C infection

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Patent: US2006/241144 A1, 2006 ;

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Cerebral function activator

Page/Page column 74

ONO PHARMACEUTICAL CO., LTD.

Patent: WO2006/38594 A1, 2006 ; Title/Abstract Full Text Show Details

component of the pharmaceutical composition

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Chemical Name: N-[1''-(11)C](4-Anisoyl)pyrrolidin-2-one Reaxys Registry Number: 8838920

Type of Substance: heterocyclic Molecular Formula: C12H13NO3

Linear Structure Formula: C11(11)CH13NO3

1 prep out of 1 reactions.

Identification

Molecular Weight: 218.229 InChI Key: ZXNRTKGTQJPIJK-DWSYCVKZSA-N

Synthesize | Hide Details Find similar Chemical Names and Synonyms N-[1''-(11)C](4-Anisoyl)pyrrolidin-2-one Identification Substance Label (1) Label

Reference

(11C)-4

Karimi; Kihlberg; Langstroem

Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 13 p. 1528 - 1531 Title/Abstract Full Text View citing articles Show Details

2 substances out of 17 reactions and 111 citations

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