3-{2-[benzyl(methyl)amino]ethyl} 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

• ChemBase编号: 504
• 分子式: C26H29N3O6
• 平均质量: 479.52496
• 单一同位素质量: 479.20563566
• SMILES: O(C(=O)C1=C(NC(=C(C1c1cc([N+](=O)[O-])ccc1)C(=O)OC)C)C)CCN(Cc1ccccc1)C
• Canonical SMILES: COC(=O)C1=C(C)NC(=C(C1c1cccc(c1)[N+](=O)[O-])C(=O)OCCN(Cc1ccccc1)C)C
• InChI: InChI=1S/C26H29N3O6/c1-17-22(25(30)34-4)24(20-11-8-12-21(15-20)29(32)33)23(18(2)27-17)26(31)35-14-13-28(3)16-19-9-6-5-7-10-19/h5-12,15,24,27H,13-14,16H2,1-4H3
• InChIKey: ZBBHBTPTTSWHBA-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 3-{2-[benzyl(methyl)amino]ethyl} 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• IUPAC传统名: nicardipine
• 商标名: Cardene; Cardene SR; Cardene IV
• 别名: Nicardipino [INN-Spanish]; Nicardipine HCl; Nicardipinum [INN-Latin]; Nicardipine

登记号

• CAS号: 55985-32-5
• PubChem SID: 160963967; 46504482
• PubChem CID: 4474

理论计算性质

JChem

• 质子受体: 6
• 质子供体: 1
• LogD (pH = 5.5): 0.67441
• LogD (pH = 7.4): 2.7083907
• Log P: 3.5586119
• 摩尔折射率: 134.7964 cm^3
• 极化性: 50.553032 Å^3
• 极化表面积: 113.69 Å^2
• 可自由旋转的化学键: 11
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 4.34
• LOG S: -5.29
• 溶解度: 2.47e-03 g/l

分子性质

理化性质

• 溶解度: 2.2 mg/L
• 疏水性(logP): 3.6

详细说明

DrugBank - DB00622

• Drug Groups: approved
• Description: A potent calcium channel blockader with marked vasodilator action. It has antihypertensive properties and is effective in the treatment of angina and coronary spasms without showing cardiodepressant effects. It has also been used in the treatment of asthma and enhances the action of specific antineoplastic agents. [PubChem]
• Indication: Used for the management of patients with chronic stable angina and for the treatment of hypertension.
• Pharmacology: Nicardipine, a dihydropyridine calcium-channel blocker, is used alone or with an angiotensin-converting enzyme inhibitor, to treat hypertension, chronic stable angina pectoris, and Prinzmetal's variant angina. Nicardipine is similar to other peripheral vasodilators. Nicardipine inhibits the influx of extra cellular calcium across the myocardial and vascular smooth muscle cell membranes possibly by deforming the channel, inhibiting ion-control gating mechanisms, and/or interfering with the release of calcium from the sarcoplasmic reticulum. The decrease in intracellular calcium inhibits the contractile processes of the myocardial smooth muscle cells, causing dilation of the coronary and systemic arteries, increased oxygen delivery to the myocardial tissue, decreased total peripheral resistance, decreased systemic blood pressure, and decreased afterload.
• Toxicity: Oral LD₅₀ Rat = 184 mg/kg, Oral LD₅₀ Mouse = 322 mg/kg
• Affected Organisms: Humans and other mammals
• Biotransformation: Nicardipine HCl is metabolized extensively by the liver.
• Absorption: While nicardipine is completely absorbed, it is subject to saturable first pass metabolism and the systemic bioavailability is about 35% following a 30 mg oral dose at steady state.
• Half Life: 8.6 hours
• Protein Binding: >95%
• Elimination: Nicardipine has been shown to be rapidly and extensively metabolized by the liver.
• Distribution: * 8.3 L/kg
• Clearance: * 0.4 L/hr?kg [Following infusion]
• External Links: Wikipedia; RxList; Drugs.com