Nicardipine

Nicardipine (Cardene) is a medication used to treat high blood pressure and angina. It belongs to the dihydropyridine class of calcium channel blockers. It is also used for Raynaud's phenomenon. It is available in by mouth and intravenous formulations. It has been used in percutaneous coronary intervention.[1] Nicardipine has been used as an alternative to sodium nitroprusside, especially because sodium nitroprusside is light sensitive and a fresh solution must be prepared.

Nicardipine
Clinical data
Trade namesCardene
AHFS/Drugs.comMonograph
MedlinePlusa695032
Routes of
administration		Oral, intravenous
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding>95%
Elimination half-life8.6 hours
Identifiers
IUPAC name
  • 2-[benzyl(methyl)amino]ethylmethyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.054.466
Chemical and physical data
FormulaC26H29N3O6
Molar mass479.533 g·mol−1
3D model (JSmol)
Melting point136–138 °C (277–280 °F)
SMILES
  • O=C(OCCN(Cc1ccccc1)C)\C2=C(\N/C(=C(/C(=O)OC)C2c3cccc([N+]([O-])=O)c3)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 Y
  • Key:ZBBHBTPTTSWHBA-UHFFFAOYSA-N Y
  (verify)

Its mechanism of action and clinical effects closely resemble those of nifedipine and the other dihydropyridines (amlodipine, felodipine), except that nicardipine is more selective for cerebral and coronary blood vessels. Nicardipine also has a longer half-life than nifedipine. Nicardipine was approved by the FDA in December 1988. The patent for both Cardene and Cardene SR expired in October 1995.[2]

It was patented in 1973 and approved for medical use in 1981.[3]

See also

References
  1. Huang RI, Patel P, Walinsky P, et al. (November 2006). "Efficacy of intracoronary nicardipine in the treatment of no-reflow during percutaneous coronary intervention". Catheterization and Cardiovascular Interventions. 68 (5): 671–6. doi:10.1002/ccd.20885. PMID 17034064. S2CID 37071966.
  2. Nicardipine at Medline PLus
  3. Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 464. ISBN 9783527607495.
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