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C8414

Sigma-Aldrich

Clobazam

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Synonym(s):
7-Chloro-1-methyl-5-phenyl-1H-1,5-benzodiazepine-2,4-(3H,5H)-dione
Empirical Formula (Hill Notation):
C16H13ClN2O2
CAS Number:
22316-47-8
Molecular Weight:
300.74
EC Number:
244-908-7
MDL number:
MFCD00079069
UNSPSC Code:
12352200
PubChem Substance ID:
24893060
NACRES:
NA.77

form

powder

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)

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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

Anxiolytic; ligand for the GABAA receptor benzodiazepine modulatory site.
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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H336,H412

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

监管及禁止进口产品

Certificates of Analysis (COA)

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Stefan Wolking et al.
Neurology, 92(11), e1238-e1249 (2019-02-10)
The aim of this study was to expand the spectrum of epilepsy syndromes related to STX1B, encoding the presynaptic protein syntaxin-1B, and establish genotype-phenotype correlations by identifying further disease-related variants. We used next-generation sequencing in the framework of research projects
A comprehensive overview of the clinical pharmacokinetics of clobazam
Tolbert Dand Larsen F
Journal of Clinical Pharmacology, 59(1), 7-19 (2019)
Matilda Bäckberg et al.
Clinical toxicology (Philadelphia, Pa.), 57(3), 203-212 (2018-10-24)
In recent years, many unclassified benzodiazepines (BZD) have appeared through online sale as new psychoactive substances (NPS). This study describes bioanalytical and clinical data related to intoxications involving NPS BZD ("designer BZD") in the Swedish STRIDA project. Case series of
Clobazam: a safe, efficacious, and newly rediscovered therapeutic for epilepsy
Gauthier AC and Mattson RH
CNS Neuroscience & Therapeutics, 21(7), 543-548 (2015)
Benzodiazepines Drive Alteration of Chromatin at the Integrated HIV-1 LTR
Elbezanti W, et al.
Viruses, 12(2), 191-191 (2020)
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