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

• ChemBase ID: 504
• Molecular Formular: C26H29N3O6
• Molecular Mass: 479.52496
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{2-[benzyl(methyl)amino]ethyl} 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• IUPAC Traditional name: nicardipine
• Brand Name: Cardene; Cardene SR; Cardene IV
• Synonyms: Nicardipino [INN-Spanish]; Nicardipine HCl; Nicardipinum [INN-Latin]; Nicardipine

Database IDs

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

CALCULATED PROPERTIES

JChem

• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 0.67441
• LogD (pH = 7.4): 2.7083907
• Log P: 3.5586119
• Molar Refractivity: 134.7964 cm^3
• Polarizability: 50.553032 Å^3
• Polar Surface Area: 113.69 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.34
• LOG S: -5.29
• Solubility (Water): 2.47e-03 g/l

PROPERTIES

Physical Property

• Solubility: 2.2 mg/L
• Hydrophobicity(logP): 3.6

DETAILS

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