C8414

Clobazam

• 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

Properties

• form: powder
• 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

Anxiolytic; ligand for the GABA_A 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.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H302,H336,H412
• Precautionary Statements: P261 - P264 - P270 - P271 - P273 - P301 + P312
• 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