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

• ChemBase编号: 233
• 分子式: C16H13ClN2O2
• 平均质量: 300.73962
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 7-chloro-1-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-2,4-dione
• IUPAC传统名: clobazam
• 商标名: Chlorepin; Clorepin; Frisium; Mystan; Urbadan; Urbanyl; Frisium, Urbanol, Onfi
• 别名: 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

登记号

• CAS号: 22316-47-8
• EC号: 244-908-7
• MDL号: MFCD00079069
• PubChem SID: 24893060; 160963696; 46506115
• PubChem CID: 2789
• CHEBI ID: 31413
• ATC码: N05BA09
• CHEMBL: 70418
• Chemspider ID: 2687
• DrugBank ID: DB00349
• KEGG ID: D01253
• 美国药典/FDA物质标识码: 2MRO291B4U
• 维基百科标题: Clobazam

理论计算性质

JChem

• Acid pKa: 4.068304
• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 1.1145105
• LogD (pH = 7.4): -0.39646015
• Log P: 2.554376
• 摩尔折射率: 80.2986 cm^3
• 极化性: 30.81095 Å^3
• 极化表面积: 40.62 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.14
• LOG S: -3.26
• 溶解度: 1.64e-01 g/l

分子性质

理化性质

• 溶解度: 188 mg/L; Chloroform
• 外观: N/AWhite Solid
• 熔点: 162-164°C
• 疏水性(logP): 2.3

安全信息

• 保存条件: Controlled Substance, -20°C Freezer
• RTECS编号: DE9600000
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 毒品管制信息: USDEA Schedule IV; Home Office Schedule 4.1; psychotrope; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

药理学性质

• 给药途径: Oral
• 生物利用度: 90%
• 排泄: Renal
• 半衰期: 18 hours
• 代谢: Hepatic
• 蛋白结合率: 83%
• 法定药品分级: Schedule IV (US); Class C (New Zealand); Class C/Sch.4 (UK)
• 妊娠期药物分类: C (US)
• 美国（FDA）药品许可证: Clobazam

详细说明

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).

参考文献

• 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)