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C8414 Sigma-Aldrich

Clobazam

Synonym: 7-Chloro-1-methyl-5-phenyl-1H-1,5-benzodiazepine-2,4-(3H,5H)-dione

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Properties

Related Categories Benzodiazepines and Anxiolytics, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, CI-CZ, Cell Biology,
Quality Level   200
drug control   USDEA Schedule IV; Home Office Schedule 4.1; psychotrope (France); kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada; psicótropo (Spain); Decreto Lei 15/93: Tabela IV (Portugal)
SMILES string   CN1C(=O)CC(=O)N(c2ccccc2)c3cc(Cl)ccc13
InChI   1S/C16H13ClN2O2/c1-18-13-8-7-11(17)9-14(13)19(16(21)10-15(18)20)12-5-3-2-4-6-12/h2-9H,10H2,1H3
InChI key   CXOXHMZGEKVPMT-UHFFFAOYSA-N
Gene Information   human ... GABRA1(2554), GABRA2(2555), GABRA3(2556), GABRA4(2557), GABRA5(2558), GABRA6(2559), GABRB1(2560), GABRB2(2561), GABRB3(2562), GABRD(2563), GABRE(2564), GABRG1(2565), GABRG2(2566), GABRG3(2567), GABRP(2568), GABRQ(55879)

Description

General description

Clobazam is a benzodiazepine, comprising of B ring nitrogen placed in positions 1 and 5 contrary to 1,4-benzodiazepines. It is a ligand for γ-aminobutyric acid type A (GABAA) receptor and is metabolized by cytochrome P450 in the liver.

Application

Clobazam has been used as a benzodiazepine to test its effect on the activation of the human immunodeficiency virus type 1 (HIV-1) long terminal repeat (LTR).

Biochem/physiol Actions

Clobazam interacts at α and γ2 subunits junction of the GABAA receptor. It is less sedative and elicits anxiolytic and anticonvulsant effects. Clobazam is more selective on the α2 subunit of the GABAA receptor than the α1 subunit. It is an antiseizure drug and is associated with antiepileptic activity. Clobazam is useful in treating chronic epileptic encephalopathy disorder, Lennox‐Gastaut syndrome. It is employed in epilepsy and seizure prevention adjunctive therapy.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
DE9600000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

LC/MS Analysis of Benzodiazepines on Ascentis® Phenyl (Analyte Mix 1)

From our library of Articles, Sigma-Aldrich presents LC/MS Analysis of Benzodiazepines on Ascentis® Phenyl (Analyte Mix 1)
Keywords: Anticonvulsants, Chromatography, Clinical, High performance liquid chromatography, Mass spectrometry, Pharmaceutical

Peer-Reviewed Papers
15

References

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