14-chloro-4,10-dimethyl-2-phenyl-3-oxa-7,10-diazatricyclo[9.4.0.02,7]pentadeca-1(11),4,12,14-tetraene-6,9-dione

• ChemBase编号: 1365
• 分子式: C20H17ClN2O3
• 平均质量: 368.81358
• 单一同位素质量: 368.09277009
• SMILES: Clc1cc2C3(OC(=CC(=O)N3CC(=O)N(c2cc1)C)C)c1ccccc1
• Canonical SMILES: CC1=CC(=O)N2C(O1)(c1ccccc1)c1cc(Cl)ccc1N(C(=O)C2)C
• InChI: InChI=1S/C20H17ClN2O3/c1-13-10-18(24)23-12-19(25)22(2)17-9-8-15(21)11-16(17)20(23,26-13)14-6-4-3-5-7-14/h3-11H,12H2,1-2H3
• InChIKey: PWAJCNITSBZRBL-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 14-chloro-4,10-dimethyl-2-phenyl-3-oxa-7,10-diazatricyclo[9.4.0.0^2,^7]pentadeca-1(11),4,12,14-tetraene-6,9-dione; 14-chloro-4,10-dimethyl-2-phenyl-3-oxa-7,10-diazatricyclo[9.4.0.0^{2,7}]pentadeca-1(11),4,12,14-tetraene-6,9-dione
• IUPAC传统名: ketazolam
• 别名: Ketazolam; 11-Chloro-8,12b-dihydro-2,8-dimethyl-12b-phenyl-4H-[1,3]oxazino[3,2-d][1,4]benzodiazepine-4,7(6H)-dione; (±)-Ketazolam; Anseren; Ansieten; Anxon; Contamex; Loftran; NSC 338158; U 28774; Unakalm

登记号

• CAS号: 27223-35-4
• PubChem SID: 160964825; 46507008
• PubChem CID: 33746
• ATC码: N05BA10
• Chemspider ID: 31110
• DrugBank ID: DB01587
• KEGG ID: D04650
• 美国药典/FDA物质标识码: 92A214MD7Y
• 维基百科标题: Ketazolam

理论计算性质

JChem

• Acid pKa: 14.1983595
• 质子受体: 3
• 质子供体: 0
• LogD (pH = 5.5): 3.0128675
• LogD (pH = 7.4): 3.0128675
• Log P: 3.0128677
• 摩尔折射率: 99.781 cm^3
• 极化性: 37.913918 Å^3
• 极化表面积: 49.85 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: 2.6
• LOG S: -3.64
• 溶解度: 8.39e-02 g/l

分子性质

药理学性质

• 给药途径: Oral
• 排泄: Renal
• 半衰期: 26-200 hours
• 代谢: Hepatic
• 法定药品分级: Schedule IV(US)

详细说明

DrugBank - DB01587

• Drug Groups: approved
• Description: Ketazolam is a drug which is a benzodiazepine derivative. It possesses anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. Ketazolam is not approved for sale in the United States or Canada.
• Indication: Ketazolam could be used for the treatment of anxiety. In approved countries, it is indicated for the treatment of anxiety, tension, irritability and similar stress related symptoms.
• Pharmacology: Benzodiazepines enhance the effect of the neurotransmitter gamma-aminobutyric acid (GABA), which results in sedative, hypnotic, anxiolytic, anticonvulsant, muscle relaxant and amnesic action.; Benzodiazepines bind nonspecifically to benzodiazepine receptors which mediate sleep, affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABA_A) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. Binding of GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.
• Toxicity: Symptoms of overdose include somnolence, confusion, coma, and diminished reflexes. Respiration, pulse and blood pressure should be monitored.
• Biotransformation: Ketazolam breaks down in the blood to diazepam which breaks down to demoxepam which breaks down to desmethyldiazepam.
• Half Life: 26-200 hours
• Elimination: Diazepam and its metabolites are excreted mainly in the urine, predominantly as their glucuronide conjugates.
• External Links: Wikipedia

Toronto Research Chemicals - K165650

A psychotropic benzodiazepine derivative with hypnotic and anxiolytic properties. Controlled Substance.

参考文献

• Sethy, V.H. et al.: Naun.-Schmeid. Atch. Pharmacol., 301, 157 (1978)
• Moore, S. et al.: Curr. Therap. Res., 29, 704 (1978)
• Gutierrez, S.F. et al.: Cien. Pharmac., 5, 37 (1978)