9,10-dimethoxy-3-(2-methylpropyl)-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-one

• ChemBase编号: 4388
• 分子式: C19H27NO3
• 平均质量: 317.42258
• 单一同位素质量: 317.19909373
• SMILES: O=C1C(CN2C(C1)c1c(CC2)cc(OC)c(OC)c1)CC(C)C
• Canonical SMILES: COc1cc2c(cc1OC)CCN1C2CC(=O)C(C1)CC(C)C
• InChI: InChI=1S/C19H27NO3/c1-12(2)7-14-11-20-6-5-13-8-18(22-3)19(23-4)9-15(13)16(20)10-17(14)21/h8-9,12,14,16H,5-7,10-11H2,1-4H3
• InChIKey: MKJIEFSOBYUXJB-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 9,10-dimethoxy-3-(2-methylpropyl)-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-one
• IUPAC传统名: tetrabenazine
• 商标名: Nitoman; Regulin; Rubigen; Xenazine
• 别名: Tetra benazin; Tetrabenazina [inn-spanish]; Tetrabenazinum [inn-latin]; Tetrabenzaine; Tetrabenzine; Tetrabenazine; (3R,11bR)-rel-1,3,4,6,7,11b-Hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-one; cis-2-Oxo-3-isobutyl-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-11bH-benzo[a]quinolizine; (+/-)-Tetrabenazine; NSC 169886; NSC 172187; Ro 1-9569; Rubigen

登记号

• CAS号: 58-46-8
• PubChem SID: 160967820; 46506426
• PubChem CID: 6018

理论计算性质

JChem

• Acid pKa: 18.239992
• 质子受体: 4
• 质子供体: 0
• LogD (pH = 5.5): 1.4955962
• LogD (pH = 7.4): 3.094543
• Log P: 3.4010618
• 摩尔折射率: 91.3074 cm^3
• 极化性: 35.678963 Å^3
• 极化表面积: 38.77 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.23
• LOG S: -2.94
• 溶解度: 3.61e-01 g/l

分子性质

理化性质

• 溶解度: Chloroform; DMSO
• 外观: White to Off-White Solid
• 熔点: 128-130°C

安全信息

• 保存条件: Refrigerator

详细说明

DrugBank - DB04844

• Drug Groups: approved
• Description: A drug formerly used as an antipsychotic but now used primarily in the treatment of various movement disorders including tardive dyskinesia. Tetrabenazine blocks uptake into adrenergic storage vesicles and has been used as a high affinity label for the vesicle transport system. [PubChem]
• Indication: For the symptomatical treatment of hyperkinetic movement disorder.
• Affected Organisms: Humans and other mammals
• Biotransformation: CYP2D6 mediated hepatic metabolism.
• Protein Binding: 82-85%
• Elimination: After oral administration, tetrabenazine is extensively hepatically metabolized, and the metabolites are primarily renally eliminated. In a mass balance study in 6 healthy volunteers, approximately 75% of the dose was excreted in the urine and fecal recovery accounted for approximately 7-16% of the dose. Urinary excretion of α-HTBZ or β-HTBZ (the major metabolites)accounted for less than 10% of the administered dose.
• Clearance: Tetrabenazine is cleared renally and fecally.
• References: Jankovic J, Beach J: Long-term effects of tetrabenazine in hyperkinetic movement disorders. Neurology. 1997 Feb;48(2):358-62. [Pubmed]
• External Links: Wikipedia; Drugs.com

Toronto Research Chemicals - T284000

Dopamine depleting agent. An antidyskinetic; antipsychotic.

参考文献

• Jankovic J, Beach J: Long-term effects of tetrabenazine in hyperkinetic movement disorders. Neurology. 1997 Feb;48(2):358-62. Pubmed
• Schwartz, et al.: Biochem. Pharmacol., 15, 645 (1966)
• Janovic, J., et al.: Ann. Neurol., 11, 41 (1966)
• Janovic, J., et al.: Neurology, 38, 391 (1966)