(1S,2S)-2-(2-{[3-(1H-1,3-benzodiazol-2-yl)propyl](methyl)amino}ethyl)-6-fluoro-1-(propan-2-yl)-1,2,3,4-tetrahydronaphthalen-2-yl 2-methoxyacetate

• ChemBase编号: 1201
• 分子式: C29H38FN3O3
• 平均质量: 495.6287232
• 单一同位素质量: 495.28972031
• SMILES: Fc1cc2c([C@@H]([C@](OC(=O)COC)(CC2)CCN(CCCc2[nH]c3c(n2)cccc3)C)C(C)C)cc1
• Canonical SMILES: COCC(=O)O[C@]1(CCN(CCCc2nc3c([nH]2)cccc3)C)CCc2c([C@@H]1C(C)C)ccc(c2)F
• InChI: InChI=1S/C29H38FN3O3/c1-20(2)28-23-12-11-22(30)18-21(23)13-14-29(28,36-27(34)19-35-4)15-17-33(3)16-7-10-26-31-24-8-5-6-9-25(24)32-26/h5-6,8-9,11-12,18,20,28H,7,10,13-17,19H2,1-4H3,(H,31,32)/t28-,29-/m0/s1
• InChIKey: HBNPJJILLOYFJU-VMPREFPWSA-N

名称和登记号

名称

• IUPAC标准名: (1S,2S)-2-(2-{[3-(1H-1,3-benzodiazol-2-yl)propyl](methyl)amino}ethyl)-6-fluoro-1-(propan-2-yl)-1,2,3,4-tetrahydronaphthalen-2-yl 2-methoxyacetate
• IUPAC传统名: @mibefradil
• 商标名: Posicor
• 别名: Mibefradil

登记号

• CAS号: 116644-53-2
• PubChem SID: 160964663; 46504498
• PubChem CID: 60663

理论计算性质

JChem

• Acid pKa: 12.543808
• 质子受体: 4
• 质子供体: 1
• LogD (pH = 5.5): 1.2434295
• LogD (pH = 7.4): 2.7534637
• Log P: 5.1569924
• 摩尔折射率: 139.7308 cm^3
• 极化性: 55.523674 Å^3
• 极化表面积: 67.45 Å^2
• 可自由旋转的化学键: 12
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 5.34
• LOG S: -5.68
• 溶解度: 1.04e-03 g/l

详细说明

DrugBank - DB01388

• Drug Groups: withdrawn
• Description: Mibefradil was withdrawn from the market in 1998 because of potentially harmful interactions with other drugs.
• Indication: For the treatment of angina and high blood pressure.
• Pharmacology: Mibefradil belongs to a group of medicines called calcium channel blocking agents, or, more commonly, calcium channel blockers. Calcium channel blocking agents affect the movement of calcium into the cells of the heart and blood vessels. As a result, they relax blood vessels and increase the supply of blood and oxygen to the heart while reducing its workload. Mibefradil is a benzimidazoyl-substituted tetraline that selectively binds and inhibits T-type calcium channels.
• Affected Organisms: Humans and other mammals
• Biotransformation: The two metabolic pathways that mibefradil undergoes are esterase-catalyzed hydrolysis of the ester side chain (producing an alcohol metabolite) and cytochrome P450 3A4-catalyzed oxidation (that becomes less important during chronic dosing). The pharmacologic effect of the metabolite is approximately 10% of that of the parent mibefradil.
• Absorption: Bioavailability after a single dose is 70%. After multiple dosing, the proportion of mibefradil undergoing first-pass metabolism is reduced, resulting in a steady state bioavailability of approximately 90%. Food does not affect the rate or extent of absorption of mibefradil.
• Half Life: 17 to 25 hours at steady state.
• Protein Binding: ≥ 99%, primarily to alpha 1-acid glycoprotein.
• External Links: Wikipedia