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C8414

Sigma-Aldrich

Clobazam

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C16H13ClN2O2
CAS Number:
Molecular Weight:
300.74
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

form

powder

Quality Level

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

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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

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Benzodiazepines Drive Alteration of Chromatin at the Integrated HIV-1 LTR
Elbezanti W, et al.
Viruses, 12(2), 191-191 (2020)
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)
A comprehensive overview of the clinical pharmacokinetics of clobazam
Tolbert Dand Larsen F
Journal of Clinical Pharmacology, 59(1), 7-19 (2019)
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

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