7-chloro-1-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-2,4-dione

• ChemBase ID: 233
• Molecular Formular: C16H13ClN2O2
• Molecular Mass: 300.73962
• Monoisotopic Mass: 300.06655535
• SMILES: Clc1cc2N(C(=O)CC(=O)N(c2cc1)C)c1ccccc1
• Canonical SMILES: Clc1ccc2c(c1)N(C(=O)CC(=O)N2C)c1ccccc1
• InChI: 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
• InChIKey: CXOXHMZGEKVPMT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-chloro-1-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-2,4-dione
• IUPAC Traditional name: clobazam
• Brand Name: Chlorepin; Clorepin; Frisium; Mystan; Urbadan; Urbanyl; Frisium, Urbanol, Onfi
• Synonyms: 7-Chloro-1-methyl-5-phenyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione; Clobazepam; Frisium; Frizium; H 4723; HR 376; LM 2717; Mystan; NSC 336279; Urbadan; Urbanyl; clobazam; Clobazam; 7-Chloro-1-methyl-5-phenyl-1H-1,5-benzodiazepine-2,4-(3H,5H)-dione; Clobazam

Database IDs

• CAS Number: 22316-47-8
• EC Number: 244-908-7
• MDL Number: MFCD00079069
• PubChem SID: 46506115; 24893060; 160963696
• PubChem CID: 2789
• CHEBI ID: 31413
• ATC CODE: N05BA09
• CHEMBL: 70418
• Chemspider ID: 2687
• DrugBank ID: DB00349
• KEGG ID: D01253
• Unique Ingredient Identifier: 2MRO291B4U
• Wikipedia Title: Clobazam

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.068304
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.1145105
• LogD (pH = 7.4): -0.39646015
• Log P: 2.554376
• Molar Refractivity: 80.2986 cm^3
• Polarizability: 30.81095 Å^3
• Polar Surface Area: 40.62 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.14
• LOG S: -3.26
• Solubility (Water): 1.64e-01 g/l

PROPERTIES

Physical Property

• Solubility: 188 mg/L; Chloroform
• Apperance: N/AWhite Solid
• Melting Point: 162-164°C
• Hydrophobicity(logP): 2.3

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer
• RTECS: DE9600000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Drug Control: USDEA Schedule IV; Home Office Schedule 4.1; psychotrope; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: 90%
• Excretion: Renal
• Half Life: 18 hours
• Metabolism: Hepatic
• Protein Bound: 83%
• Legal Status: Schedule IV (US); Class C (New Zealand); Class C/Sch.4 (UK)
• Pregnancy Category: C (US)
• US Licence: Clobazam

DETAILS

DrugBank - DB00349

• Drug Groups: illicit; approved; investigational
• Description: Clobazam is a drug which is a benzodiazepine derivative. It has been marketed as an anxiolytic since 1975 and an anticonvulsant since 1984. [Wikipedia]
• Indication: For treatment and management of epilepsy and anxiety disorder.
• Pharmacology: Clobazam is a barbiturate used in combination with acetaminophen or aspirin and caffeine for its sedative and relaxant effects in the treatment of tension headaches, migraines, and pain.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Clobazam has two major metabolites: N-desmethyl-clobazam and 4'-hydroxyclobazam, the former of which is active. The demethylation is facilitated by CYP2C19, CYP3A4, and CYP2B6 and the 4'-hydroxyclobazam by CYP2C18 and CYP2C19.
• Absorption: Bioavailability is 90%.
• Half Life: 18 hours
• Protein Binding: 83%
• References: Freche C: [Study of an anxiolytic, clobazam, in otorhinolaryngology in psychosomatic pharyngeal manifestations] Sem Hop Ther. 1975 Apr;51(4):261-3. [Pubmed] ; : Clobazam in treatment of refractory epilepsy: the Canadian experience. A retrospective study. Canadian Clobazam Cooperative Group. Epilepsia. 1991 May-Jun;32(3):407-16. [Pubmed] ; Wildin JD, Pleuvry BJ, Mawer GE, Onon T, Millington L: Respiratory and sedative effects of clobazam and clonazepam in volunteers. Br J Clin Pharmacol. 1990 Feb;29(2):169-77. [Pubmed] ; Kilpatrick C, Bury R, Fullinfaw R, Moulds R: Clobazam in the treatment of epilepsy. Clin Exp Neurol. 1987;23:139-44. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - C8414

Biochem/physiol Actions
Anxiolytic; ligand for the GABAA receptor benzodiazepine modulatory site.

Toronto Research Chemicals - C582500

Benzodiazepine psychotherapeutic agent. Clobazam (CLB) has proven efficacy against multiple seizure types. An anxiolytic; anticonvulsant. Controlled substance (depressant).

REFERENCES

• Freche C: [Study of an anxiolytic, clobazam, in otorhinolaryngology in psychosomatic pharyngeal manifestations] Sem Hop Ther. 1975 Apr;51(4):261-3. Pubmed
• : Clobazam in treatment of refractory epilepsy: the Canadian experience. A retrospective study. Canadian Clobazam Cooperative Group. Epilepsia. 1991 May-Jun;32(3):407-16. Pubmed
• Wildin JD, Pleuvry BJ, Mawer GE, Onon T, Millington L: Respiratory and sedative effects of clobazam and clonazepam in volunteers. Br J Clin Pharmacol. 1990 Feb;29(2):169-77. Pubmed
• Kilpatrick C, Bury R, Fullinfaw R, Moulds R: Clobazam in the treatment of epilepsy. Clin Exp Neurol. 1987;23:139-44. Pubmed
• Gastaut, H., et al.: Epilepsia, 20, 437 (1979)
• Guberman, A., et al.: Can J. Neurol. Sci., 17, 311 (1979)
• Munn, R., et al.: Pediatr. Neurol. 9, 465 (1979)