nicardipine   Click here for help

GtoPdb Ligand ID: 2559

Synonyms: (R,S)-nicardipine | Cardene®
Approved drug
nicardipine is an approved drug (FDA (1988))
Compound class: Synthetic organic
Comment: One of the dihydropyridine class of drugs.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 11
Topological polar surface area 111.01
Molecular weight 479.21
XLogP 4.87
No. Lipinski's rules broken 1
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Canonical SMILES COC(=O)C1=C(C)NC(=C(C1c1cccc(c1)[N+](=O)[O-])C(=O)OCCN(Cc1ccccc1)C)C
Isomeric 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
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Summary of Clinical Use Click here for help
Nicardipine acts as a vasodilator and has anti-hypertensive properties. Used in the treatment of angina and coronary spasms, nicardipine has also been used in asthma treatment.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Nicardipine inhibits the influx of extracellular calcium across the myocardial and vascular smooth muscle cell membranes, by means of three mechanisms: deforming calcium channels, inhibiting ion-control gating mechanisms and and interfering with the release of calcium from the sarcoplasmic reticulum. This results in a decrease in intracellular calcium which inhibits the contractile processes of the myocardial smooth muscle, which leads to 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.
Due to the complex nature of this drug's MMOA, and the paucity of (human) affinity data, we do not tag a primary drug target.
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