3-ethyl-3-phenylpiperidine-2,6-dione (Glutethimide) by Asch

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9 substances in Reaxys

2016-06-01 21h:25m:34s (EST)

O HN O

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Reaxys ID 84989 View in Reaxys

1/9 CAS Registry Number: 77-21-4; 17575-58-5; 17575-59-6; 18389-24-7 Chemical Name: Glutethimide; 3-ethyl-3-phenylglutarimide; 3ethyl-3-phenyl-2,6-piperidinedione; glutethimide; 3-ethyl-3-phenylpiperidine-2,6-dione; 3-phenyl-3-ethylpiperidine-2,6-dione; (rac)-Glutethimid Linear Structure Formula: C13H15NO2 Molecular Formula: C13H15NO2 Molecular Weight: 217.268 Type of Substance: heterocyclic InChI Key: JMBQKKAJIKAWKF-UHFFFAOYSA-N Note:

O HN O

Substance Label (7) Label References 13

Qian, Xiaofei; Han, Jianwei; Wang, Limin; Advanced Synthesis and Catalysis; vol. 358; nb. 6; (2016); p. 940 - 946, View in Reaxys

Takaya, Hikaru; Yoshida, Kazunori; Isozaki, Katsuhiro; Terai, Hiroki; Murahashi, Shun-Ichi; Angewandte Chemie - International Edition; vol. 42; nb. 28; (2003); p. 3302 - 3304, View in Reaxys

Bajdor; Glice; Les; Adamowicz; Kolos; Journal of Molecular Structure; vol. 511-512; (1999); p. 107 - 116, View in Reaxys; Glice; Bajdor; Les; Stepanenko; Nowak; Aboul-Enein; Chilmonczyk; Journal of Molecular Structure; vol. 560; nb. 1-3; (2001); p. 137 - 149, View in Reaxys

Chang, Meng-Yang; Chang, Bo-Rui; Tai, Huo-Mu; Chang, Nein-Chen; Tetrahedron Letters; vol. 41; nb. 52; (2000); p. 10273 - 10276, View in Reaxys

starting to III(A,B)

Soine, William H.; Yu, Cheng-Fang; Thomas, Diana; Cao, Si Lan; Westkaemper, Richard B.; Williams, Todd D.; Medicinal Chemistry Research; vol. 6; nb. 3; (1996); p. 174 - 189, View in Reaxys

GLUT

Kimmett; Whitney; Marks; Molecular Pharmacology; vol. 49; nb. 4; (1996); p. 676 - 682, View in Reaxys; Nims; Lubet; Diwan; Mellini; Utermahlen Jnr; Thomas; ; vol. 9; nb. 5; (1994); p. 269 - 278, View in Reaxys

(rac)-7

Blaschke, Gottfried; Kraft, Horst Peter; Markgraf, Hildegunde; Chemische Berichte; vol. 116; nb. 11; (1983); p. 3611 - 3617, View in Reaxys

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Schollmayer, Erwin; Sachse, Richard; Braun, Marina; US2008/274061; (2008); (A1) English, View in Reaxys

Related Structure (1) References Bonamico et al.; Gazzetta Chimica Italiana; vol. 90; (1960); p. 1607,1614, View in Reaxys Melting Point (22) 1 of 22

Melting Point [°C]

Bourgeois et al.; Organic Mass Spectrometry; vol. 9; (1974); p. 53,56, View in Reaxys; Schleuder; Duerrbeck; Jira; Pharmazie; vol. 53; nb. 6; (1998); p. 381 - 386, View in Reaxys 2 of 22

Melting Point [°C]

86 - 88

Solvent (Melting Point)

methanol; H2O

Hartmann, Rolf W.; Batzl, Christine; Journal of Medicinal Chemistry; vol. 29; nb. 8; (1986); p. 1362 - 1369, View in Reaxys 3 of 22

Melting Point [°C]

85 - 86

Wesolowski et al.; Journal of Pharmaceutical Sciences; vol. 57; (1968); p. 811,814, View in Reaxys 4 of 22

Melting Point [°C]

83 - 85

Patent; Pliva; NL283796; (1965); Chem.Abstr.; vol. 63; nb. 9881e; (1965), View in Reaxys 5 of 22

Melting Point [°C]

86 - 88

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Brandstaetter-Kuhnert; Kofler; Scientia Pharmaceutica; vol. 27; (1959); p. 73,74-81; Chem.Abstr.; nb. 9210; (1960), View in Reaxys; Patent; Lodzkie Zaklady Farm. 'Polfa'; PL53907; (1965); Chem.Abstr.; vol. 68; nb. 77997s; (1968), View in Reaxys 6 of 22

Melting Point [°C]

68.5 - 70.5

Patent; Lodzkie Zaklady Farmaceutyczne 'Polfa'; NL6405774; (1963); Chem.Abstr.; vol. 62; nb. 11743a; (1965), View in Reaxys 7 of 22

Melting Point [°C]

Shefber; Higuchi; Journal of Pharmaceutical Sciences; vol. 52; (1963); p. 781,785, View in Reaxys 8 of 22

Melting Point [°C]

Shefber; Higuchi; Journal of Pharmaceutical Sciences; vol. 52; (1963); p. 781,785, View in Reaxys 9 of 22

Melting Point [°C]

80 - 85

Patent; Taisho Pharmaceutical Co., Ltd.; JP2084964; (1961); Chem.Abstr.; vol. 62; nb. 10384c; (1965), View in Reaxys 10 of 22

Melting Point [°C]

82 - 83

Solvent (Melting Point)

propan-2-ol

Kukolja et al.; Croatica Chemica Acta; vol. 33; (1961); p. 41,42, View in Reaxys 11 of 22

Melting Point [°C]

72 - 82

Bonamico et al.; Gazzetta Chimica Italiana; vol. 90; (1960); p. 1607,1614, View in Reaxys 12 of 22

Melting Point [°C]

72 - 82

Solvent (Melting Point)

aq. ethanol

Bonamico et al.; Gazzetta Chimica Italiana; vol. 90; (1960); p. 1607,1614, View in Reaxys 13 of 22

Melting Point [°C]

80 - 82

Solvent (Melting Point)

aq. ethanol

Branchini et al.; Farmaco, Edizione Scientifica; vol. 15; (1960); p. 734,744, 745, 746, 756, View in Reaxys 14 of 22

Melting Point [°C]

86 - 88

Solvent (Melting Point)

ethyl acetate; petroleum ether

Branchini et al.; Farmaco, Edizione Scientifica; vol. 15; (1960); p. 734,744, 745, 746, 756, View in Reaxys 15 of 22

Melting Point [°C]

86 - 88

Solvent (Melting Point)

petroleum ether

Bonamico et al.; Gazzetta Chimica Italiana; vol. 90; (1960); p. 1607,1614, View in Reaxys 16 of 22

Melting Point [°C]

Brandstaetter-Kuhnert; Kuhnert; Scientia Pharmaceutica; vol. 28; (1960); p. 287,302; Chem.Abstr.; nb. 9210; (1960), View in Reaxys 17 of 22

Melting Point [°C]

85 - 87

Patent; Pakleppa; DD16295; (1959); Chem.Abstr.; vol. 55; nb. 575e; (1961), View in Reaxys 18 of 22

Melting Point [°C]

91 - 92

Solvent (Melting Point)

aq. ethanol

Penprase; Biles; Journal of the American Pharmaceutical Association (1912-1977); vol. 47; (1958); p. 523,528, View in Reaxys 19 of 22

Melting Point [°C]

87 - 87.5

Solvent (Melting Point)

diethyl ether; petroleum ether

Hoffmann et al.; Helvetica Chimica Acta; vol. 40; (1957); p. 387,394, View in Reaxys 20 of 22

Melting Point [°C]

84 - 87

Solvent (Melting Point)

propan-2-ol

Bernhard et al.; Helvetica Chimica Acta; vol. 39; (1956); p. 596,603, View in Reaxys

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21 of 22

Melting Point [°C]

83 - 84

Solvent (Melting Point)

diethyl ether

Salmon-Legagneur; Neveu; Bulletin de la Societe Chimique de France; (1953); p. 70,74, View in Reaxys 22 of 22

Melting Point [°C]

82 - 86

Solvent (Melting Point)

ethyl acetate; petroleum ether

Tagmann et al.; Helvetica Chimica Acta; vol. 35; (1952); p. 1541,1545, View in Reaxys Boiling Point (1) Boiling Point [°C] 168

Pressure (Boiling Point) [Torr]

References

0.3

Patent; Pakleppa; DD16295; (1959); Chem.Abstr.; vol. 55; nb. 575e; (1961), View in Reaxys

Refractive Index (1) Refractive Index Wavelength (Refractive Index) [nm]

Temperature (Refractive Index) [°C]

References

1.5403

Brandstaetter-Kuhnert; Kofler; Scientia Pharmaceutica; vol. 27; (1959); p. 73,74-81; Chem.Abstr.; nb. 9210; (1960), View in Reaxys

589

Adsorption (MCS) (2) 1 of 2

Description (Adsorption (MCS))

Adsorption isotherm

Solvent (Adsorption (MCS))

H2O

Temperature (Adsorption (MCS)) [°C]

Partner (Adsorption (MCS))

styrene-divinylbenzene-copolymerizate of wofatite-Y-type

Pflegel; Dittgen; Dutz; Pharmazie; vol. 36; nb. 4; (1981); p. 300 - 301, View in Reaxys 2 of 2

Description (Adsorption (MCS))

Adsorption

Sellers; Khouw; Dolman; Journal of Pharmaceutical Sciences; vol. 66; nb. 11; (1977); p. 1640 - 1641, View in Reaxys Association (MCS) (7) 1 of 7

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

CDCl3

Partner (Association (MCS))

C38H36N6O6

Chang; Van Engen; Fan; Hamilton; Journal of the American Chemical Society; vol. 113; nb. 20; (1991); p. 7640 7645, View in Reaxys 2 of 7

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

CCl4

Temperature (Association (MCS)) [°C]

21.9

Partner (Association (MCS))

compound 4

Schneider, Hans-Joerg; Juneja, Ravindra K.; Simova, Svetlana; Chemische Berichte; vol. 122; (1989); p. 1211 1214, View in Reaxys 3 of 7

Description (Association Stability constant of the complex with ... (MCS))

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Solvent (Association (MCS))

CDCl3

Temperature (Association (MCS)) [°C]

21.9

Partner (Association (MCS))

compound 4

Schneider, Hans-Joerg; Juneja, Ravindra K.; Simova, Svetlana; Chemische Berichte; vol. 122; (1989); p. 1211 1214, View in Reaxys 4 of 7

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

CDCl3

Temperature (Association (MCS)) [°C]

21.9

Partner (Association (MCS))

N,N'-(2,6-pyridinediyl)bis(acetamide); N-(3-Butyrylamino-phenyl)-butyramide

Schneider, Hans-Joerg; Juneja, Ravindra K.; Simova, Svetlana; Chemische Berichte; vol. 122; (1989); p. 1211 1214, View in Reaxys 5 of 7

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

CDCl3

Temperature (Association (MCS)) [°C]

21.9

Partner (Association (MCS))

5-cyclohex-1-enyl-1,3,5-trimethyl-pyrimidine-2,4,6-trione; N-(3-Butyrylamino-phenyl)-butyramide

Schneider, Hans-Joerg; Juneja, Ravindra K.; Simova, Svetlana; Chemische Berichte; vol. 122; (1989); p. 1211 1214, View in Reaxys 6 of 7

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

CCl4

Temperature (Association (MCS)) [°C]

21.9

Partner (Association (MCS))

5-cyclohex-1-enyl-1,3,5-trimethyl-pyrimidine-2,4,6-trione; N,N'-2,6-pyridinediylbislt;butanamidegt;

Schneider, Hans-Joerg; Juneja, Ravindra K.; Simova, Svetlana; Chemische Berichte; vol. 122; (1989); p. 1211 1214, View in Reaxys 7 of 7

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

CDCl3

Temperature (Association (MCS)) [°C]

21.9

Partner (Association (MCS))

5-cyclohex-1-enyl-1,3,5-trimethyl-pyrimidine-2,4,6-trione; N,N'-2,6-pyridinediylbislt;butanamidegt;

Schneider, Hans-Joerg; Juneja, Ravindra K.; Simova, Svetlana; Chemische Berichte; vol. 122; (1989); p. 1211 1214, View in Reaxys Crystal Phase (3) Description (Crys- Comment (Crystal References tal Phase) Phase) Solid state structure properties

Branchini et al.; Farmaco, Edizione Scientifica; vol. 15; (1960); p. 734,744, 745, 746, 756, View in Reaxys

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Crystal structure determination

Interplanar spacing

Bonamico et al.; Gazzetta Chimica Italiana; vol. 90; (1960); p. 1607,1614, View in Reaxys Penprase; Biles; Journal of the American Pharmaceutical Association (1912-1977); vol. 47; (1958); p. 523,528, View in Reaxys

Crystal Property Description (1) Colour & Other References Properties white

Qian, Xiaofei; Han, Jianwei; Wang, Limin; Advanced Synthesis and Catalysis; vol. 358; nb. 6; (2016); p. 940 - 946, View in Reaxys

Crystal System (1) References Bonamico et al.; Gazzetta Chimica Italiana; vol. 90; (1960); p. 1607,1614, View in Reaxys Dissociation Exponent (1) 1 of 1

Comment (Dissociation Exponent)

(pk')pK

Doornbos; de Zeeuw; Pharmaceutisch Weekblad; vol. 104; (1969); p. 233,241, View in Reaxys Electrochemical Behaviour (1) Description (Elec- References trochemical Behaviour) Electrolytic dissociation / protonation equilibrium

Mueller; Die Pharmazie; vol. 37; nb. 6; (1982); p. 416 - 419, View in Reaxys

Further Information (9) Description (Fur- References ther Information) Further information

Ford; Rubinstein; Journal of Pharmacy and Pharmacology; vol. 30; nb. 8; (1978); p. 512 - 513, View in Reaxys

Further information

Rebagay; DeLuca; Journal of Pharmaceutical Sciences; vol. 65; (1976); p. 1645,1646,1647, View in Reaxys

Further information

Aboul-Enein (Ed. K.Florey); Analytical Profiles of Drug Substances, Vol.5; (1976); p. 139, View in Reaxys

Further information

Fales et al.; Archives of Mass Spectral Data; vol. 2; (1971); p. 596, View in Reaxys

Further information

Furman; Journal - Association of Official Analytical Chemists; vol. 51; (1968); p. 1111,1115, View in Reaxys

Further information

Reubke; Mollica; Journal of Pharmaceutical Sciences; vol. 56; (1967); p. 822,824, View in Reaxys

Further information

Bates; Gibaldi; Kanig; Journal of pharmaceutical sciences; vol. 55; nb. 2; (1966); p. 191 - 199, View in Reaxys

Further information

Haycock et al.; Journal of the American Pharmaceutical Association, Scientific Edition; vol. 49; (1960); p. 673,676, View in Reaxys

Further information

Goldbaum; Williams; Analytical Chemistry; vol. 32; (1960); p. 81,82, View in Reaxys

Liquid/Liquid Systems (MCS) (4) 1 of 4

Description (Liquid/ Liquid Systems (MCS))

Distribution between solvent 1 + 2

Partner (Liquid/Liquid Systems (MCS))

octanol; H2O

Hansch; Bjorkroth; Leo; Journal of Pharmaceutical Sciences; vol. 76; nb. 9; (1987); p. 663 - 687, View in Reaxys 2 of 4

Description (Liquid/ Liquid Systems (MCS))

Distribution between solvent 1 + 2

Partner (Liquid/Liquid Systems (MCS))

water, chloroform

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Mueller; Die Pharmazie; vol. 37; nb. 6; (1982); p. 416 - 419, View in Reaxys 3 of 4

Description (Liquid/ Liquid Systems (MCS))

Distribution between solvent 1 + 2

Partner (Liquid/Liquid Systems (MCS))

water, diethyl ether

Mueller; Die Pharmazie; vol. 37; nb. 6; (1982); p. 416 - 419, View in Reaxys 4 of 4

Description (Liquid/ Liquid Systems (MCS))

Distribution between solvent 1 + 2

Solvent (Liquid/Liquid Systems (MCS))

various solvent(s); H2O

Temperature (Liquid/ Liquid Systems (MCS)) [°C]

Comment (Liquid/Liquid Systems (MCS))

Ratio of solvents: 1:1 (V:V)

Partner (Liquid/Liquid Systems (MCS))

1.) n-Octanol; 2.) Phosphatpuffer

Pflegel; Dittgen; Dutz; Pharmazie; vol. 36; nb. 4; (1981); p. 300 - 301, View in Reaxys Liquid/Solid Systems (MCS) (1) 1 of 1

Description (Liquid/Solid Eutectic Systems (MCS)) Brandstaetter-Kuhnert; Kofler; Scientia Pharmaceutica; vol. 27; (1959); p. 73,74-81; Chem.Abstr.; nb. 9210; (1960), View in Reaxys

Solubility (MCS) (2) 1 of 2

Ford; Rubinstein; Journal of Pharmacy and Pharmacology; vol. 30; nb. 8; (1978); p. 512 - 513, View in Reaxys; Rebagay; DeLuca; Journal of Pharmaceutical Sciences; vol. 65; (1976); p. 1645,1646,1647, View in Reaxys

2 of 2

Comment (Solubility (MCS))

relat. Loesungsgeschw. in 13.4percent-ig. A. bei 25grad u. 40grad

Shefber; Higuchi; Journal of Pharmaceutical Sciences; vol. 52; (1963); p. 781,785, View in Reaxys Space Group (1) References Bonamico et al.; Gazzetta Chimica Italiana; vol. 90; (1960); p. 1607,1614, View in Reaxys NMR Spectroscopy (5) 1 of 5

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Qian, Xiaofei; Han, Jianwei; Wang, Limin; Advanced Synthesis and Catalysis; vol. 358; nb. 6; (2016); p. 940 946, View in Reaxys 2 of 5

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

101

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Location

supporting information

Qian, Xiaofei; Han, Jianwei; Wang, Limin; Advanced Synthesis and Catalysis; vol. 358; nb. 6; (2016); p. 940 946, View in Reaxys 3 of 5

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Chang, Meng-Yang; Chang, Bo-Rui; Tai, Huo-Mu; Chang, Nein-Chen; Tetrahedron Letters; vol. 41; nb. 52; (2000); p. 10273 - 10276, View in Reaxys 4 of 5

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Chang, Meng-Yang; Chang, Bo-Rui; Tai, Huo-Mu; Chang, Nein-Chen; Tetrahedron Letters; vol. 41; nb. 52; (2000); p. 10273 - 10276, View in Reaxys 5 of 5

Description (NMR Spec- NMR troscopy) Vinkler; Nemeth; Stajer; Sohar; Jerkovich; Archiv der Pharmazie; vol. 309; nb. 4; (1976); p. 265 - 273, View in Reaxys

IR Spectroscopy (16) 1 of 16

Description (IR Spectroscopy)

Spectrum

Solvent (IR Spectroscopy)

CS2

Comment (IR Spectroscopy)

concentration dependence

Glice; Bajdor; Les; Stepanenko; Nowak; Aboul-Enein; Chilmonczyk; Journal of Molecular Structure; vol. 560; nb. 1-3; (2001); p. 137 - 149, View in Reaxys 2 of 16

Description (IR Spectroscopy)

Spectrum

Solvent (IR Spectroscopy)

acetonitrile

Comment (IR Spectroscopy)

concentration dependence

Glice; Bajdor; Les; Stepanenko; Nowak; Aboul-Enein; Chilmonczyk; Journal of Molecular Structure; vol. 560; nb. 1-3; (2001); p. 137 - 149, View in Reaxys 3 of 16

Description (IR Spectroscopy)

Spectrum

Solvent (IR Spectroscopy)

CS2

Bajdor; Glice; Les; Adamowicz; Kolos; Journal of Molecular Structure; vol. 511-512; (1999); p. 107 - 116, View in Reaxys 4 of 16

Description (IR Spectroscopy)

Spectrum

Solvent (IR Spectroscopy)

CCl4

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Bajdor; Glice; Les; Adamowicz; Kolos; Journal of Molecular Structure; vol. 511-512; (1999); p. 107 - 116, View in Reaxys 5 of 16

Description (IR Spectroscopy)

Spectrum

Solvent (IR Spectroscopy)

solid Ar

Temperature (IR Spectroscopy) [°C]

-251.15 - -228.15

Comment (IR Spectroscopy)

temperature dependence

Bajdor; Glice; Les; Adamowicz; Kolos; Journal of Molecular Structure; vol. 511-512; (1999); p. 107 - 116, View in Reaxys 6 of 16

Description (IR Spectroscopy)

Spectrum

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

solid

Bajdor; Glice; Les; Adamowicz; Kolos; Journal of Molecular Structure; vol. 511-512; (1999); p. 107 - 116, View in Reaxys 7 of 16

Description (IR Spectroscopy)

Spectrum

Solvent (IR Spectroscopy)

CHCl3

Comment (IR Spectroscopy)

concentration dependence

Bajdor; Glice; Les; Adamowicz; Kolos; Journal of Molecular Structure; vol. 511-512; (1999); p. 107 - 116, View in Reaxys 8 of 16

Description (IR Spectroscopy)

Spectrum

Solvent (IR Spectroscopy)

CCl4

Comment (IR Spectroscopy)

3600 - 1650 cm**(-1)

Glice, Magdalena M.; Les, Andrzej; Bajdor, Krzysztof; Journal of Molecular Structure; vol. 450; nb. 1-3; (1998); p. 141 - 153, View in Reaxys 9 of 16

Description (IR Spectroscopy)

Spectrum

Solvent (IR Spectroscopy)

acetonitrile

Comment (IR Spectroscopy)

3600 - 1650 cm**(-1)

Glice, Magdalena M.; Les, Andrzej; Bajdor, Krzysztof; Journal of Molecular Structure; vol. 450; nb. 1-3; (1998); p. 141 - 153, View in Reaxys 10 of 16

Description (IR Spectroscopy)

Spectrum

Solvent (IR Spectroscopy)

CHCl3

Comment (IR Spectroscopy)

3600 - 1650 cm**(-1)

Glice, Magdalena M.; Les, Andrzej; Bajdor, Krzysztof; Journal of Molecular Structure; vol. 450; nb. 1-3; (1998); p. 141 - 153, View in Reaxys

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11 of 16

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

3192 - 1687 cm**(-1)

Glice, Magdalena M.; Les, Andrzej; Bajdor, Krzysztof; Journal of Molecular Structure; vol. 450; nb. 1-3; (1998); p. 141 - 153, View in Reaxys 12 of 16

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

gaseous matrix

Comment (IR Spectroscopy)

3402 - 1716 cm**(-1)

Glice, Magdalena M.; Les, Andrzej; Bajdor, Krzysztof; Journal of Molecular Structure; vol. 450; nb. 1-3; (1998); p. 141 - 153, View in Reaxys 13 of 16

Description (IR Spectroscopy)

Intensity of IR bands

Glice, Magdalena M.; Les, Andrzej; Bajdor, Krzysztof; Journal of Molecular Structure; vol. 450; nb. 1-3; (1998); p. 141 - 153, View in Reaxys 14 of 16

Description (IR Spectroscopy)

Hayden et al.; Journal of the Association of Official Agricultural Chemists; vol. 45; (1962); p. 797,831, View in Reaxys; Vinkler; Nemeth; Stajer; Sohar; Jerkovich; Archiv der Pharmazie; vol. 309; nb. 4; (1976); p. 265 273, View in Reaxys 15 of 16

Description (IR Spectroscopy)

Spectrum

Furman; Journal - Association of Official Analytical Chemists; vol. 51; (1968); p. 1111,1115, View in Reaxys; Smith; Journal of Pharmaceutical Sciences; vol. 53; (1964); p. 942, View in Reaxys; Kukolja; Polak; Croatica Chemica Acta; vol. 32; (1960); p. 23,24-30; Chem.Abstr.; nb. 20975; (1960), View in Reaxys 16 of 16

Description (IR Spectroscopy)

Spectrum

Solvent (IR Spectroscopy)

CH2Cl2

Comment (IR Spectroscopy)

5000 - 1250 cm**(-1)

Kebrle et al.; Helvetica Chimica Acta; vol. 42; (1959); p. 417,418, View in Reaxys Mass Spectrometry (1) References Milne et al.; Analytical Chemistry; vol. 43; (1971); p. 1815,1817, View in Reaxys; Fales et al.; Archives of Mass Spectral Data; vol. 2; (1971); p. 596, View in Reaxys; Bourgeois et al.; Organic Mass Spectrometry; vol. 9; (1974); p. 53,56, View in Reaxys UV/VIS Spectroscopy (4) 1 of 4

Description (UV/VIS Spectroscopy)

Absorption maxima

Kracmar; Kracmarova; Cesko-Slovenska Farmacie; vol. 15; (1966); p. 16,18, View in Reaxys 2 of 4

Description (UV/VIS Spectroscopy)

Spectrum

Champy-Hatem; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 260; (1965); p. 4208, View in Reaxys; Haycock et al.; Journal of the American Pharmaceutical Association, Scientific Edition; vol. 49; (1960); p. 673,676, View in Reaxys; Smith; Journal of Pharmaceutical Sciences; vol. 53; (1964); p. 942, View in Reaxys; Goldbaum; Williams; Analytical Chemistry; vol. 32; (1960); p. 81,82, View in Reaxys 3 of 4

Description (UV/VIS Spectroscopy)

UV/VIS

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Hayden et al.; Journal of the Association of Official Agricultural Chemists; vol. 45; (1962); p. 797,831, View in Reaxys 4 of 4

Description (UV/VIS Spectroscopy)

Spectrum

Solvent (UV/VIS Spectroscopy)

ethanol

Comment (UV/VIS Spectroscopy)

210 - 280 nm

Kebrle; Hoffmann; Helvetica Chimica Acta; vol. 39; (1956); p. 767,775, View in Reaxys Raman Spectroscopy (7) Description (Ram- Solvent (Raman an Spectroscopy) Spectroscopy)

Comment (Raman Spectroscopy)

References

Spectrum

solid

Bajdor; Glice; Les; Adamowicz; Kolos; Journal of Molecular Structure; vol. 511-512; (1999); p. 107 - 116, View in Reaxys

Spectrum

CHCl3

Bajdor; Glice; Les; Adamowicz; Kolos; Journal of Molecular Structure; vol. 511-512; (1999); p. 107 - 116, View in Reaxys

Bands

CCl4

Glice, Magdalena M.; Les, Andrzej; Bajdor, Krzysztof; Journal of Molecular Structure; vol. 450; nb. 1-3; (1998); p. 141 - 153, View in Reaxys

Bands

CDCl3

Glice, Magdalena M.; Les, Andrzej; Bajdor, Krzysztof; Journal of Molecular Structure; vol. 450; nb. 1-3; (1998); p. 141 - 153, View in Reaxys

Bands

CHCl3

Glice, Magdalena M.; Les, Andrzej; Bajdor, Krzysztof; Journal of Molecular Structure; vol. 450; nb. 1-3; (1998); p. 141 - 153, View in Reaxys

Bands

KBr

Glice, Magdalena M.; Les, Andrzej; Bajdor, Krzysztof; Journal of Molecular Structure; vol. 450; nb. 1-3; (1998); p. 141 - 153, View in Reaxys

Bands

acetonitrile

Glice, Magdalena M.; Les, Andrzej; Bajdor, Krzysztof; Journal of Molecular Structure; vol. 450; nb. 1-3; (1998); p. 141 - 153, View in Reaxys

Fluorescence Spectroscopy (1) Description (Fluo- References rescence Spectroscopy) Fluorescence

Haycock et al.; Journal of the American Pharmaceutical Association, Scientific Edition; vol. 49; (1960); p. 673,676, View in Reaxys

Pharmacological Data (14) 1 of 14

Comment (Pharmacological Data)

Bioactivities present

Aeberli; Gogerty; Houlihan; Iorio; Journal of Medicinal Chemistry; vol. 19; nb. 3; (1976); p. 436 - 438, View in Reaxys; Kondo,Y.; Witkop,B.; Journal of Organic Chemistry; vol. 33; nb. 1; (1968); p. 206 - 212, View in Reaxys; Patent; Novartis AG; Novartis Pharma GmbH; EP907663; (2004); (B1) English, View in Reaxys; Patent; Renshaw, Perry F.; Cohen, Bruce M.; US2006/39890; (2006); (A1) English, View in Reaxys; Penprase; Biles; Journal of the American Pharmaceutical Association (1912-1977); vol. 47; (1958); p. 523,528, View in Reaxys; Patent; CIBA; US2673205; (1952), View in Reaxys; Patent; CIBA; DE950193; (1952), View in Reaxys; Tagmann et al.; Helvetica Chimica Acta; vol. 35; (1952); p. 1541,1545, View in Reaxys; Kebrle et al.; Helvetica Chimica Acta; vol. 42; (1959); p. 417,418, View in Reaxys; Hoffmann et al.; Helvetica Chimica Acta; vol. 40; (1957); p. 387,394, View in Reaxys; Tagmann et al.; Helvetica Chimica Acta; vol. 37; (1954); p. 185,189, View in Reaxys; Urech et al.; Helvetica Chimica Acta; vol. 36; (1953); p. 1809,1814, View in Reaxys; Kebrle; Hoffmann; Helvetica Chimica Acta; vol. 39; (1956); p. 767,775, View in Reaxys; Patent; CIBA; US2848455; (1956), View in Reaxys; Salmon-Legagneur; Neveu; Bulletin de la Societe Chimique de France; (1953); p. 70,74, View in Reaxys; Bernhard et al.; Helvetica Chimica Acta; vol. 39; (1956); p. 596,603, View in Reaxys; Milne et al.; Analytical Chemistry; vol. 43; (1971); p. 1815,1817, View in Reaxys; Kracmar; Kracmarova; Cesko-Slovenska Farmacie; vol. 15; (1966); p. 16,18, View in Reaxys; Brandstaetter-Kuhnert; Kuhnert; Scientia Pharmaceutica; vol. 28; (1960); p. 287,302; Chem.Abstr.; nb. 9210; (1960), View in Reaxys; Reubke; Mollica; Journal of Pharmaceutical Sciences; vol. 56; (1967); p. 822,824, View in Reaxys; Ott; Hardtmann; Denzer; Frey; Gogerty; Leslie; Trapold; Journal of medicinal chemistry; vol. 11; nb. 4; (1968); p. 777 - 787, View in Reaxys; Champy-Hatem; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 260; (1965); p. 4208, View in Reaxys; Haycock et al.; Journal of the American Pharmaceutical Association, Scientific Edition; vol. 49;

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(1960); p. 673,676, View in Reaxys; Hardtmann et al.; Journal of Medicinal Chemistry; vol. 14; (1971); p. 878,881, View in Reaxys; Branchini et al.; Farmaco, Edizione Scientifica; vol. 15; (1960); p. 734,744, 745, 746, 756, View in Reaxys; Shefber; Higuchi; Journal of Pharmaceutical Sciences; vol. 52; (1963); p. 781,785, View in Reaxys; Furman; Journal - Association of Official Analytical Chemists; vol. 51; (1968); p. 1111,1115, View in Reaxys; Bonamico et al.; Gazzetta Chimica Italiana; vol. 90; (1960); p. 1607,1614, View in Reaxys; Sellers; Khouw; Dolman; Journal of Pharmaceutical Sciences; vol. 66; nb. 11; (1977); p. 1640 - 1641, View in Reaxys; Doornbos; de Zeeuw; Pharmaceutisch Weekblad; vol. 104; (1969); p. 233,241, View in Reaxys; Fales et al.; Archives of Mass Spectral Data; vol. 2; (1971); p. 596, View in Reaxys; Bourgeois et al.; Organic Mass Spectrometry; vol. 9; (1974); p. 53,56, View in Reaxys; Hayden et al.; Journal of the Association of Official Agricultural Chemists; vol. 45; (1962); p. 797,831, View in Reaxys; Brandstaetter-Kuhnert; Kofler; Scientia Pharmaceutica; vol. 27; (1959); p. 73,74-81; Chem.Abstr.; nb. 9210; (1960), View in Reaxys; Schaefer; Justus Liebigs Annalen der Chemie; vol. 729; (1969); p. 234, View in Reaxys; Testa et al.; Justus Liebigs Annalen der Chemie; vol. 676; (1964); p. 151,159, View in Reaxys; Patent; Lodzkie Zaklady Farmaceutyczne 'Polfa'; NL6405774; (1963); Chem.Abstr.; vol. 62; nb. 11743a; (1965), View in Reaxys; Smith; Journal of Pharmaceutical Sciences; vol. 53; (1964); p. 942, View in Reaxys; Vinkler; Nemeth; Stajer; Sohar; Jerkovich; Archiv der Pharmazie; vol. 309; nb. 4; (1976); p. 265 273, View in Reaxys; Patent; Lodzkie Zaklady Farm. 'Polfa'; PL53907; (1965); Chem.Abstr.; vol. 68; nb. 77997s; (1968), View in Reaxys; Patent; Pliva; NL283796; (1965); Chem.Abstr.; vol. 63; nb. 9881e; (1965), View in Reaxys; Patent; Taisho Pharmaceutical Co., Ltd.; JP2084964; (1961); Chem.Abstr.; vol. 62; nb. 10384c; (1965), View in Reaxys; Goldbaum; Williams; Analytical Chemistry; vol. 32; (1960); p. 81,82, View in Reaxys; Hilz; Linde; Pelster; Die Pharmazie; vol. 26; nb. 5; (1971); p. 312 - 313, View in Reaxys; Ford; Rubinstein; Journal of Pharmacy and Pharmacology; vol. 30; nb. 8; (1978); p. 512 - 513, View in Reaxys; Bates; Gibaldi; Kanig; Journal of pharmaceutical sciences; vol. 55; nb. 2; (1966); p. 191 - 199, View in Reaxys; Rebagay; DeLuca; Journal of Pharmaceutical Sciences; vol. 65; (1976); p. 1645,1646,1647, View in Reaxys; Patent; Pakleppa; DD16295; (1959); Chem.Abstr.; vol. 55; nb. 575e; (1961), View in Reaxys; Kukolja et al.; Croatica Chemica Acta; vol. 33; (1961); p. 41,42, View in Reaxys; Aboul-Enein (Ed. K.Florey); Analytical Profiles of Drug Substances, Vol.5; (1976); p. 139, View in Reaxys; Wesolowski et al.; Journal of Pharmaceutical Sciences; vol. 57; (1968); p. 811,814, View in Reaxys; Kukolja; Polak; Croatica Chemica Acta; vol. 32; (1960); p. 23,24-30; Chem.Abstr.; nb. 20975; (1960), View in Reaxys; Yamana; Mizukami; Yakugaku Zasshi; vol. 81; (1961); p. 1383,1386; Chem.Abstr.; vol. 56; nb. 7433; (1962), View in Reaxys; Pavlov; Bogavac; Arsenijevic; Pharmazie; vol. 45; nb. 4; (1990); p. 286 - 287, View in Reaxys; Bagley; Thomas; Rudo; Spencer; Doorley; Ossipov; Jerussi; Benvenga; Spaulding; Journal of Medicinal Chemistry; vol. 34; nb. 2; (1991); p. 827 - 841, View in Reaxys; Chang; Van Engen; Fan; Hamilton; Journal of the American Chemical Society; vol. 113; nb. 20; (1991); p. 7640 - 7645, View in Reaxys; Blaschke, Gottfried; Kraft, Horst Peter; Markgraf, Hildegunde; Chemische Berichte; vol. 116; nb. 11; (1983); p. 3611 - 3617, View in Reaxys; Pflegel; Dittgen; Dutz; Pharmazie; vol. 36; nb. 4; (1981); p. 300 - 301, View in Reaxys; Mueller; Die Pharmazie; vol. 37; nb. 6; (1982); p. 416 - 419, View in Reaxys; Foster; Jarman; Leung; Rowlands; Taylor; Journal of Medicinal Chemistry; vol. 26; nb. 1; (1983); p. 50 - 54, View in Reaxys; Tschiersch; Schwabe; Pharmazie; vol. 43; nb. 5; (1988); p. 352 - 354, View in Reaxys; Feibush; Figueroa; Charles; et al.; Journal of the American Chemical Society; vol. 108; nb. 12; (1986); p. 3310 - 3318, View in Reaxys; Graves, Penelope E.; Uzgiris, Vytautas I.; Salhanick, Hilton A.; Steroids; vol. 35; nb. 5; (1980); p. 543 - 560, View in Reaxys; Schneider, HansJoerg; Juneja, Ravindra K.; Simova, Svetlana; Chemische Berichte; vol. 122; (1989); p. 1211 - 1214, View in Reaxys; Ellis; Schwan; Wessels; Miles; Journal of Pharmaceutical Sciences; vol. 69; nb. 10; (1980); p. 1194 - 1198, View in Reaxys; Hartmann, Rolf W.; Batzl, Christine; Journal of Medicinal Chemistry; vol. 29; nb. 8; (1986); p. 1362 - 1369, View in Reaxys; Bednarski; Hartmann; Archiv der Pharmazie; vol. 326; nb. 7; (1993); p. 391 - 394, View in Reaxys; Hansch; Bjorkroth; Leo; Journal of Pharmaceutical Sciences; vol. 76; nb. 9; (1987); p. 663 - 687, View in Reaxys; Sparatore; Novelli; Farmaco; vol. 52; nb. 8-9; (1997); p. 509 - 521, View in Reaxys; Glice, Magdalena M.; Les, Andrzej; Bajdor, Krzysztof; Journal of Molecular Structure; vol. 450; nb. 1-3; (1998); p. 141 - 153, View in Reaxys; Schleuder; Duerrbeck; Jira; Pharmazie; vol. 53; nb. 6; (1998); p. 381 - 386, View in Reaxys; Soine, William H.; Yu, Cheng-Fang; Thomas, Diana; Cao, Si Lan; Westkaemper, Richard B.; Williams, Todd D.; Medicinal Chemistry Research; vol. 6; nb. 3; (1996); p. 174 - 189, View in Reaxys; Danilovski, Aleksandar; Vinkovic, Mladen; Filic, Darko; Acta Crystallographica Section C: Crystal Structure Communications; vol. 55; nb. 8; (1999); p. 1300 - 1304, View in Reaxys; Kimmett; Whitney; Marks; Molecular Pharmacology; vol. 49; nb. 4; (1996); p. 676 - 682, View in Reaxys; Nims; Lubet; Diwan; Mellini; Utermahlen Jnr; Thomas; ; vol. 9; nb. 5; (1994); p. 269 - 278, View in Reaxys; Bajdor; Glice; Les; Adamowicz; Kolos; Journal of Molecular Structure; vol. 511-512; (1999); p. 107 - 116, View in Reaxys; Chang, Meng-Yang; Chang, Bo-Rui; Tai, Huo-Mu; Chang, Nein-Chen; Tetrahedron Letters; vol. 41; nb. 52; (2000); p. 10273 - 10276, View in Reaxys; Glice; Bajdor; Les; Stepanenko; Nowak; Aboul-Enein; Chilmonczyk; Journal of Molecular Structure; vol. 560; nb. 1-3; (2001); p. 137 - 149, View in Reaxys; Bruno-Blanch; Galvez; Garcia-Domenech; Bioorganic and Medicinal Chemistry Letters; vol. 13; nb. 16; (2003); p. 2749 - 2754, View in Reaxys; Takaya, Hikaru; Yoshida, Kazunori; Isozaki, Katsuhiro; Terai, Hiroki; Murahashi, Shun-Ichi; Angewandte Chemie - International Edition; vol. 42; nb. 28; (2003); p. 3302 - 3304, View in Reaxys; Votano, Joseph R.; Parham, Marc; Hall, L. Mark; Hall, Lowell H.; Kier, Lemont B.; Oloff, Scott; Tropsha, Alexander; Journal of Medicinal Chemistry; vol. 49; nb. 24; (2006); p. 7169 - 7181, View in Reaxys; Lee, Chow H.; Edwards, Anthony M.; Archives of Toxicology; vol. 77; nb. 3; (2003); p. 150 - 159, View in Reaxys; Patent; Schollmayer, Erwin; Sachse, Richard; Braun, Marina; US2008/274061; (2008); (A1) English, View in Reaxys; Patent; Bristol, David William; King, Clifford Riley; Mitchener, JR., Joseph Pike; Audia, Vicki Haynes; US2008/293695; (2008); (A1) English, View in Reaxys; He, Bao-Jiang; Yin, Chuan-Qi; Li, ShiRong; Bai, Zheng-Wu; Chirality; vol. 22; nb. 1; (2010); p. 69 - 76, View in Reaxys; Patent; Cambridge University Technical Services Ltd.; US7238711; (2007); (B1) English, View in Reaxys; Dai, Zhi; Ye, Guozhong; Pittman Jr., Charles U.; Li, Tingyu; Chirality; vol. 24; nb. 4; (2012); p. 329 - 338, View in Reaxys; Aeberli; Gogerty; Houlihan; Journal of medicinal chemistry; vol. 10; nb. 4; (1967); p. 636 - 642, View in Reaxys; Loev; Macko; Fried; Journal of medicinal chemistry; vol. 12; nb. 5; (1969); p. 854 - 859, View in Reaxys; Malec; Flis; Kleinrok; Acta poloniae phar-

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maceutica; vol. 32; nb. 2; (1975); p. 243 - 249, View in Reaxys; Paul; Williams; Cohen; Journal of Medicinal Chemistry; vol. 17; nb. 5; (1974); p. 539 - 541, View in Reaxys; Greenblatt; Allen; Koch Weser; Shader; American Journal of Diseases of Children; vol. 130; nb. 5; (1976); p. 507 - 511, View in Reaxys; Maenpaa; Sigusch; Raunio; Syngelma; Vuorela; Pelkonen; Biochemical Pharmacology; vol. 45; nb. 5; (1993); p. 1035 - 1042, View in Reaxys; Graves; Uzgiris; Salhanick; Steroids; vol. 35; nb. 5; (1980); p. 543 - 559, View in Reaxys; Hardtmann; Huegi; Journal of medicinal chemistry; vol. 14; nb. 9; (1971); p. 878 - 882, View in Reaxys; Wright; Roscoe; JAMA : the journal of the American Medical Association; vol. 214; nb. 9; (1970); p. 1704 - 1706, View in Reaxys; Patent; Grainger; David J.; Tatalick; Lauren Marie; (182 pag.); US7238711; (2007), View in Reaxys; Patent; YOUNG, James, W.; BRANDT, Steven; (42 pag.); WO2009/310788; (1993); (A1), View in Reaxys; WITKIN, L B; SPITALETTA, P; PLUMMER, A J; Arch Int Pharmacodyn Ther (1899-1996); vol. 124; (1960); p. 105 - 15, View in Reaxys; ; (2012); Type: Review, Lab: EFF_071212, Owner: EFFECT, Number: 000, Revision: 07.12.2012 00:00:00, View in Reaxys; Donald C. Hobbs; Hugh M. Mcllhenny; Annual reports in medicinal chemistry; vol. 11; (1976); p. 190 - 199, View in Reaxys; Marvin Cohen; Annual reports in medicinal chemistry; vol. 11; (1976); p. 13 - 22, View in Reaxys; Tredger JM; Stoll S; Hospital pharmacy; vol. 9; (2002); p. 167 - 173, View in Reaxys; Aventis, Doriden (Glutethimide), Product Leaflet, View in Reaxys; Journal of forensic sciences; vol. 5; (1960); p. 217, View in Reaxys; Journal of forensic sciences; vol. 4; (1959); p. 111, View in Reaxys; Gross F; Tripod J; Meier R; Schweizerische medizinische Wochenschrift; vol. 85; nb. 13; (1955); p. 305 - 309, View in Reaxys; Poisoning; Toxicology, Symptoms, Treatments, 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970, 2, 73.; vol. 2; (1970); p. 73, View in Reaxys; MCBAY AJ; KATSAS GG; The New England journal of medicine; vol. 257; nb. 3; (1957); p. 97 - 100, View in Reaxys; Clarke's Analysis of Drugs and Poisons, View in Reaxys; Toxicology and applied pharmacology; vol. 29; (1974); p. 75, View in Reaxys; Journal of Medical Society of Toho University.; vol. 7; (1960); p. 513, View in Reaxys; Psychotropic Drugs and Related Compounds, 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972, 233.; (1972); p. 233, View in Reaxys; Y Al-Tarakji-Khalfh; C Cave; S Menager; Y Legras; C Combet Farnoux; O Lafont; European journal of medicinal chemistry; vol. 28; (1993); p. 593 - 600, View in Reaxys; http:// www2.siri.org/msds/tox/f/q59/q572.html, View in Reaxys; http://www.pharmgkb.org/do/serve?objId=PA164749505&objCls=Drug, View in Reaxys; http://www.intox.org/databank/documents/pharm/glutethi/ pim246.htm, View in Reaxys; http://iccvam.niehs.nih.gov/methods/invidocs/brdvalstdy/appK3.pdf, View in Reaxys; Patent; David J. Grainger; Lauren Marie Tatalick; US2008/45557; (A1); (2008), View in Reaxys; Patent; Lauren Marie Tatalick; David J. Grainger; US7989466; (B2); (2011), View in Reaxys; Patent; Timothy J. Barberich; US2005/267176; (A1); (2005), View in Reaxys; Qian, Xiaofei; Han, Jianwei; Wang, Limin; Advanced Synthesis and Catalysis; vol. 358; nb. 6; (2016); p. 940 - 946, View in Reaxys 2 of 14

Effect (Pharmacological Data)

MCP-1-induced THP-1 cells migration; inhibition of

Species or Test-System (Pharmacological Data)

THP-1 monocyte cells of human

Method (Pharmacological Data)

The ED50 (the concentration required to inhibit by 50percent the migration induced by MCP-1 in the chemotaxis assay) for a number of agents is summarized in Table 13. For each agent tested, a single "wide-range" assay was performed testing concentrations of the agent between 1100 pM and 100 μM (FIG. 5 1) and MCP-1, RANTES or MIP-1α. Similar data has been generated for SDF-1α and IL-8 (see Table 14). Once an estimate of the working range has been obtained in these "wide-range" assays, "narrow-range" assays are performed 2 logs either side of the estimated ED50 (FIG. 51). This is repeated three times to obtain an accurate estimate of the functional ED50.

Type (Pharmacological Data)

ED50

Value of Type (Pharmacological Data)

50 μmol/l

Location

Page/Page column 143

Patent; Cambridge University Technical Services Ltd.; US7238711; (2007); (B1) English, View in Reaxys 3 of 14

Effect (Pharmacological Data)

gene expression; induction of

Species or Test-System (Pharmacological Data)

Wistar rat hepatocytes

Sex

male

Concentration (Pharmacological Data)

0.5 mmol/l

Method (Pharmacological Data)

cells incubated with title comp. and epidermal growth factor for 2 h; total RNA extracted; cmyc mRNA expression analyzed by Northern blotting

Further Details (Pharmacological Data)

control: untreated cells; positive control: epidermal growth factor + 17β-estradiol treated cells

Results

title comp. induced c-myc expression level by 1.8-fold; fig.

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Lee, Chow H.; Edwards, Anthony M.; Archives of Toxicology; vol. 77; nb. 3; (2003); p. 150 - 159, View in Reaxys 4 of 14

Effect (Pharmacological Data)

gene expression; effect on

Species or Test-System (Pharmacological Data)

Wistar rat hepatocytes

Sex

male

Concentration (Pharmacological Data)

0.5 mmol/l

Method (Pharmacological Data)

cells incubated with title comp. in presence or absence of epidermal growth factor for 1 h; total RNA extracted; c-fos mRNA expression analyzed by Northern blotting

Comment (Pharmacological Data)

No effect

Lee, Chow H.; Edwards, Anthony M.; Archives of Toxicology; vol. 77; nb. 3; (2003); p. 150 - 159, View in Reaxys 5 of 14

Comment (Pharmacological Data)

effect on CNS and analgesic activity in mice (test, effect, dose): anti-metrazol, significant anticovulsant activity, 150 mg/kg, p.o.

Sparatore; Novelli; Farmaco; vol. 52; nb. 8-9; (1997); p. 509 - 521, View in Reaxys 6 of 14

Effect (Pharmacological Data)

metabolic

Species or Test-System (Pharmacological Data)

mouse liver microsomes

Sex

not specified

Concentration (Pharmacological Data)

2 mmol/l

Exposure Period (Pharmacological Data)

30 min

Method (Pharmacological Data)

3.5-5.0 mg freshly prepared microsomal protein incubated in the presence of 2 mM/l phenobarbital, 8 mM/l MgCl2, 250 μM/l UDP-D-glucose, 5 μCi UDP-D-<3H>glucose at pH 7.3 (ACES buffer); 37 deg C

Further Details (Pharmacological Data)

radiochemical assay for determining percent inhibition

Results

50 percent inhibition

Soine, William H.; Yu, Cheng-Fang; Thomas, Diana; Cao, Si Lan; Westkaemper, Richard B.; Williams, Todd D.; Medicinal Chemistry Research; vol. 6; nb. 3; (1996); p. 174 - 189, View in Reaxys 7 of 14

Effect (Pharmacological Data)

metabolic

Species or Test-System (Pharmacological Data)

mouse liver microsomes

Sex

not specified

Concentration (Pharmacological Data)

2 mmol/l

Exposure Period (Pharmacological Data)

30 min

Method (Pharmacological Data)

3.5-5.0 mg freshly prepared microsomal protein incubated in the presence of 2 mM/l phenobarbital, 8 mM/l MgCl2, 250 μM/l UDP-D-glucose at pH 7.3 (ACES buffer); 37 deg C

Further Details (Pharmacological Data)

rate (pmol/min/mg prot) of formation of N-glucoside conjugate measured with standard assay

Results

no N-glucoside conjugate formed

Comment (Pharmacological Data)

No effect

Soine, William H.; Yu, Cheng-Fang; Thomas, Diana; Cao, Si Lan; Westkaemper, Richard B.; Williams, Todd D.; Medicinal Chemistry Research; vol. 6; nb. 3; (1996); p. 174 - 189, View in Reaxys

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8 of 14

Effect (Pharmacological Data)

drug interaction

Species or Test-System (Pharmacological Data)

chick embryo

Concentration (Pharmacological Data)

4 mg

Kind of Dosing (Pharmacological Data)

4 mg/egg for 1 day in 0.1 ml of DMSO

Method (Pharmacological Data)

fertilized eggs of white leghorn strain, injected with an inducer of P450 isozymes; title comp. in water; incubated for 19 days; at 24 h after treatment, inj. 4 mg of TTMS

Further Details (Pharmacological Data)

embryos liver removed, N-vinylPP dimethyl ester mixture filtered, separated into regioisomers by HPLC

Results

amount of all four regioisomers of N-vinylPP were greater than in the untreated chick embryos; ND regioisomer constituted a greater percentage

Kimmett; Whitney; Marks; Molecular Pharmacology; vol. 49; nb. 4; (1996); p. 676 - 682, View in Reaxys 9 of 14

Effect (Pharmacological Data)

enzyme; induction of

Species or Test-System (Pharmacological Data)

B6C3F1 mice

Sex

male

Route of Application

peroral

Concentration (Pharmacological Data)

468 ppm

Exposure Period (Pharmacological Data)

14 h

Method (Pharmacological Data)

of diet; mice 8 weeks old; diet: Purina Lab Chowpercent5010; drinking water and diet ad libitum; hepatic response

Further Details (Pharmacological Data)

daily dose of comp.: 92 mg/kg; temp. 68-72 deg F; humidity ca. 50 percent

Results

immunoreactive hepatic cytochrome P450 2B: 193 (control: 6); ethoxyresorufin O-dealkylation activity: 29 pmol/min/mg S-9 protein (control: 8); benzyloxyresorufin O-dealkylation activity: 141 pmol/min/mg S-9 protein (control: 11)

Nims; Lubet; Diwan; Mellini; Utermahlen Jnr; Thomas; ; vol. 9; nb. 5; (1994); p. 269 - 278, View in Reaxys 10 of 14

Comment (Pharmacological Data)

no inhibibion of desmolase (50 μg/ml) and aromatase (20 μg/ml)

Tschiersch; Schwabe; Pharmazie; vol. 43; nb. 5; (1988); p. 352 - 354, View in Reaxys 11 of 14

Comment (Pharmacological Data)

noninhibitor of desmolase and aromatase

Foster; Jarman; Leung; Rowlands; Taylor; Journal of Medicinal Chemistry; vol. 26; nb. 1; (1983); p. 50 - 54, View in Reaxys 12 of 14

Comment (Pharmacological Data)

inhib. of cholesterol side chain cleavage in mitochondria from bovine adrenal cortex, bovine corpus luteum and human term placenta

Graves, Penelope E.; Uzgiris, Vytautas I.; Salhanick, Hilton A.; Steroids; vol. 35; nb. 5; (1980); p. 543 - 560, View in Reaxys 13 of 14

Comment (Pharmacological Data)

stimulation and depression, ED 50 for anti-TBZ, anti-PTZ, anti-Iso, anti-Picro, anti-PTZ, anti-Strych, anti-Harm = 100, 23, 36, >100, 33, >100, >100, respectively, LD 50 = 595 mg/kg (mice)

Ellis; Schwan; Wessels; Miles; Journal of Pharmaceutical Sciences; vol. 69; nb. 10; (1980); p. 1194 - 1198, View in Reaxys 14 of 14

Comment (Pharmacological Data)

Tab. II

Hardtmann et al.; Journal of Medicinal Chemistry; vol. 14; (1971); p. 878,881, View in Reaxys

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Use (2) Use Pattern

References

Anti-abuse

Patent; Bristol, David William; King, Clifford Riley; Mitchener, JR., Joseph Pike; Audia, Vicki Haynes; US2008/293695; (2008); (A1) English, View in Reaxys

depressant

Patent; Renshaw, Perry F.; Cohen, Bruce M.; US2006/39890; (2006); (A1) English, View in Reaxys

Reaxys ID 84988 View in Reaxys

2/9 CAS Registry Number: 17575-58-5 Chemical Name: glutethimide; (R)-3-ethyl-3-phenyl-piperidine-2,6-dione; (R)-3-Aethyl-3-phenyl-piperidin-2,6-dion Linear Structure Formula: C13H15NO2 Molecular Formula: C13H15NO2 Molecular Weight: 217.268 Type of Substance: heterocyclic InChI Key: JMBQKKAJIKAWKF-CYBMUJFWSA-N Note:

O HN O

Related Structure (1) Related Structure References Konfiguration:. Purification (2) Purification (method)

Knabe; Reischig; Archiv der Pharmazie; vol. 311; nb. 7; (1978); p. 634 - 636, View in Reaxys; Finch; Dziemian; Cohen; Steinetz; Experientia; vol. 31; nb. 9; (1975); p. 1002 - 1003, View in Reaxys References

GC using a Chiraldex%TM&-BPH column

Schleuder; Duerrbeck; Jira; Pharmazie; vol. 53; nb. 6; (1998); p. 381 - 386, View in Reaxys

resolution of the racemat by chromatography on cellulose triacetate, 87percent opt. yield

Blaschke, Gottfried; Kraft, Horst Peter; Markgraf, Hildegunde; Chemische Berichte; vol. 116; nb. 11; (1983); p. 3611 - 3617, View in Reaxys

Melting Point (2) 1 of 2

Melting Point [°C]

95 - 96

Fogliato; Fronza; Fuganti; Grasselli; Servi; Journal of Organic Chemistry; vol. 60; nb. 17; (1995); p. 5693 - 5695, View in Reaxys 2 of 2

Melting Point [°C]

103 - 104

Solvent (Melting Point)

ethyl acetate; petroleum ether

Branchini et al.; Ricerca Scientifica; vol. 29; (1959); p. 2435, View in Reaxys Electrical Moment (1) 1 of 1

Description (Electrical Moment)

Dipole moment

Comment (Electrical Moment)

in Dioxan, ε : 2.830

Lee et al.; Journal of the American Chemical Society; vol. 83; (1961); p. 4586,4589, View in Reaxys Optical Rotatory Power (2) 1 of 2

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1 g/100ml

Solvent (Optical Rotatory Power)

methanol

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Optical Rotatory Power [deg]

181

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Fogliato; Fronza; Fuganti; Grasselli; Servi; Journal of Organic Chemistry; vol. 60; nb. 17; (1995); p. 5693 - 5695, View in Reaxys 2 of 2

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

c=1

Solvent (Optical Rotatory Power)

ethanol

Optical Rotatory Power [deg]

184

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Branchini et al.; Ricerca Scientifica; vol. 29; (1959); p. 2435, View in Reaxys NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Fogliato; Fronza; Fuganti; Grasselli; Servi; Journal of Organic Chemistry; vol. 60; nb. 17; (1995); p. 5693 - 5695, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Lee et al.; Journal of the American Chemical Society; vol. 83; (1961); p. 4586,4589, View in Reaxys UV/VIS Spectroscopy (1) 1 of 1

Description (UV/VIS Spectroscopy)

Absorption maxima

Lee et al.; Journal of the American Chemical Society; vol. 83; (1961); p. 4586,4589, View in Reaxys

Reaxys ID 6273502 View in Reaxys

3/9 CAS Registry Number: 17575-59-6 Chemical Name: glutethimide; (S)-glutethimide Linear Structure Formula: C13H15NO2 Molecular Formula: C13H15NO2 Molecular Weight: 217.268 Type of Substance: heterocyclic InChI Key: JMBQKKAJIKAWKF-ZDUSSCGKSA-N Note:

O HN O

Purification (1) Purification (method)

References

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GC using a Chiraldex%TM&-BPH column

Schleuder; Duerrbeck; Jira; Pharmazie; vol. 53; nb. 6; (1998); p. 381 - 386, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

100.6

Solvent (Melting Point)

diethyl ether; hexane

Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166, View in Reaxys Optical Rotatory Power (2) 1 of 2

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

-190

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166, View in Reaxys 2 of 2

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1 g/100ml

Solvent (Optical Rotatory Power)

methanol

Optical Rotatory Power [deg]

-181.5

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Fadel; Garcia-Argote; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1159 - 1166, View in Reaxys

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Reaxys ID 678567 View in Reaxys

4/9 CAS Registry Number: 65960-31-8 Linear Structure Formula: C13H10D5NO2 Molecular Formula: C13H15NO2 Molecular Weight: 222.228 Type of Substance: heterocyclic InChI Key: JMBQKKAJIKAWKF-DKFMXDSJSA-N Note:

O HN 2H

2H 2H

Substance Label (1) Label References 1

Aboul-Enein; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 13; (1977); p. 509,510,512, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

80 - 82

Aboul-Enein; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 13; (1977); p. 509,510,512, View in Reaxys Mass Spectrometry (1) References Aboul-Enein; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 13; (1977); p. 509,510,512, View in Reaxys

Reaxys ID 6804570 View in Reaxys

5/9 Chemical Name: glutethimide Linear Structure Formula: C13H15NO2 Molecular Formula: C13H15NO2 Molecular Weight: 217.268 Type of Substance: heterocyclic InChI Key: JMBQKKAJIKAWKF-UHFFFAOYSA-N Note:

O HN O

(+)-enantiomer

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

alpha

Solvent (Optical Rotatory Power)

propan-2-ol; hexane

Optical Rotatory Power [deg]

1.08

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Comment (Optical Rota- Ratio of solvents: 10:90 tory Power) Armstrong, Daniel W.; Tang, Yubing; Chen, Shushi; Zhou, Yiwen; Bagwill, Christina; Chen, Jing-Ran; Analytical Chemistry; vol. 66; nb. 9; (1994); p. 1473 - 1484, View in Reaxys

Reaxys ID 8061748 View in Reaxys

6/9

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Linear Structure Formula: C13H14DNO2 Molecular Formula: C13H15NO2 Molecular Weight: 218.26 Type of Substance: heterocyclic InChI Key: JMBQKKAJIKAWKF-DYCDLGHISA-N Note:

N O

IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Spectrum

Solvent (IR Spectroscopy)

CDCl3

Comment (IR Spectroscopy)

3600 - 3000 cm**(-1)

Glice, Magdalena M.; Les, Andrzej; Bajdor, Krzysztof; Journal of Molecular Structure; vol. 450; nb. 1-3; (1998); p. 141 - 153, View in Reaxys

Reaxys ID 8172102 View in Reaxys

7/9 Chemical Name: (3RS)-glutethimide potassium salt Linear Structure Formula: C13H14NO2 (1-)*K(1+) Molecular Formula: C13H14NO2*K Molecular Weight: 255.358 Type of Substance: heterocyclic InChI Key: DTEVEJCGMHBRBP-UHFFFAOYSA-M Note:

O –N

K+

Melting Point (1) 1 of 1

Melting Point [°C]

116 - 118

Soine, William H.; Yu, Cheng-Fang; Thomas, Diana; Cao, Si Lan; Westkaemper, Richard B.; Williams, Todd D.; Medicinal Chemistry Research; vol. 6; nb. 3; (1996); p. 174 - 189, View in Reaxys

Reaxys ID 8473513 View in Reaxys

8/9 Chemical Name: 3-ethyl-3-phenyl-2,6-piperidinedione dimer; glutethimide dimer Type of Substance: polymer (monomers given) Composition: Comp. Name: 3-ethyl-3-phenylglutarimide Note:

No Structure

IR Spectroscopy (2) 1 of 2

Description (IR Spectroscopy)

Spectrum

Solvent (IR Spectroscopy)

CHCl3

Comment (IR Spectroscopy)

concentration dependence

Bajdor; Glice; Les; Adamowicz; Kolos; Journal of Molecular Structure; vol. 511-512; (1999); p. 107 - 116, View in Reaxys 2 of 2

Description (IR Spectroscopy)

Spectrum

Solvent (IR Spectroscopy)

solid Ar

Temperature (IR Spectroscopy) [°C]

22 - 45

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Comment (IR Spectroscopy)

temperature dependence

Bajdor; Glice; Les; Adamowicz; Kolos; Journal of Molecular Structure; vol. 511-512; (1999); p. 107 - 116, View in Reaxys

Reaxys ID 21120320 View in Reaxys O

H N

9/9 Linear Structure Formula: C13H14NO2 Molecular Formula: C13H14NO2 Molecular Weight: 216.26 InChI Key: CVULOKMFOYBWDU-ZDUSSCGKSA-N Note:

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