(1S,9S)-9-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}-10-oxo-octahydro-1H-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid

• ChemBase编号: 1172
• 分子式: C22H31N3O5
• 平均质量: 417.49864
• 单一同位素质量: 417.22637111
• SMILES: O=C1N2N(CCC[C@H]2C(=O)O)CCC[C@@H]1N[C@@H](CCc1ccccc1)C(=O)OCC
• Canonical SMILES: CCOC(=O)[C@@H](N[C@H]1CCCN2N(C1=O)[C@@H](CCC2)C(=O)O)CCc1ccccc1
• InChI: InChI=1S/C22H31N3O5/c1-2-30-22(29)18(13-12-16-8-4-3-5-9-16)23-17-10-6-14-24-15-7-11-19(21(27)28)25(24)20(17)26/h3-5,8-9,17-19,23H,2,6-7,10-15H2,1H3,(H,27,28)/t17-,18-,19-/m0/s1
• InChIKey: HHHKFGXWKKUNCY-FHWLQOOXSA-N

名称和登记号

名称

• IUPAC标准名: (1S,9S)-9-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}-10-oxo-octahydro-1H-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid
• IUPAC传统名: inhibace
• 别名: Inhibace; Cilazapril; (1S,9S)-9-[[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]octahydro-10-oxo-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxylic Acid; Ro 31-2848; Vascace; Yipingshu

登记号

• CAS号: 92077-78-6; 88768-40-5
• PubChem SID: 160964635
• PubChem CID: 56330

理论计算性质

JChem

• Acid pKa: 3.4099488
• 质子受体: 6
• 质子供体: 2
• LogD (pH = 5.5): -0.26813108
• LogD (pH = 7.4): -1.4383031
• Log P: -0.007882288
• 摩尔折射率: 110.5637 cm^3
• 极化性: 43.8066 Å^3
• 极化表面积: 99.18 Å^2
• 可自由旋转的化学键: 9
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -0.2
• LOG S: -2.59
• 溶解度: 1.06e+00 g/l

分子性质

理化性质

• 溶解度: Chloroform; DMSO; Methanol
• 外观: White to Off-White Solid
• 熔点: 95-97°C

安全信息

• 保存条件: -20°C Freezer

详细说明

DrugBank - DB01340

• Drug Groups: approved
• Description: One of the angiotensin-converting enzyme inhibitors (ACE inhibitors) used for hypertension. It is a prodrug that is hydrolyzed after absorption to its main metabolite cilazaprilat. [PubChem]
• Indication: Cilazapril is an ACE inhibtor class drug used in the treatment of hypertension and heart failure.
• Pharmacology: Cilazapril inhibits the production angiotensin II. By doing so, it decreases sodium and water reabsorption (via aldosterone) and it decreases vasoconstriction. The combined effect of this is a decrease in vascular resistance, and therefore, blood pressure.
• External Links: Wikipedia

Toronto Research Chemicals - C441200

An ACE inhibitor. Hydrolyzed in vivo to the active diacid metabolite (Cilazaprilat). Antihypertensive.

参考文献

• Natoff, I.L., et al.: J. Cardiovasc. Pharmacol., 7, 569 (1985)
• Szucs, T., et al.: Drugs, 41, Suppl.1, 18 (1985)
• Pordy, R.C., et al.: Cardiology, 86, 41 (1985)