Nicardipine

Nicardipine (Cardene) is a medication used to treat high blood pressure and angina. It belongs to the dihydropyridine class of calcium channel blockers (CCBs). 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

Clinical data
Trade names	Cardene
AHFS/Drugs.com	Monograph
MedlinePlus	a695032
Routes of administration	Oral, intravenous
ATC code	C08CA04 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding	>95%
Elimination half-life	8.6 hours
Identifiers
IUPAC name 2-[benzyl(methyl)amino]ethylmethyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
CAS Number	55985-32-5 Y
PubChem CID	4474
IUPHAR/BPS	2559
DrugBank	DB00622 Y
ChemSpider	4319 Y
UNII	CZ5312222S
KEGG	D08270 Y
ChEBI	CHEBI:7550
ChEMBL	ChEMBL1484 Y
CompTox Dashboard (EPA)	DTXSID6023363
ECHA InfoCard	100.054.466
Chemical and physical data
Formula	C26H29N3O6
Molar mass	479.533 g·mol−1
3D model (JSmol)	Interactive image
Melting point	136–138 °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
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Its mechanism of action and clinical effects closely resemble those of nifedipine and the other dihydropyridine calcium channel blockers (amlodipine, felodipine), except that nicardipine is more selective for cerebral and coronary blood vessels. It is primarily a peripheral arterial vasodilator, thus unlike the nitrovasodilators (nitroglycerin and nitroprusside), cardiac preload is minimally affected. It has the longest duration among parenteral CCBs.^[2][3] As its use may lead to reflex tachycardia, it is advisable to use it in conjunction with a beta-blocker.^[3][2]

It was patented in 1973 and approved for medical use in 1981.^[4]

Nicardipine was approved by the FDA in December 1988. The patent for both Cardene and Cardene SR expired in October 1995.^[5]

See also

• Calcium channel blocker toxicity

References

1. Huang RI, Patel P, Walinsky P, Fischman DL, Ogilby JD, Awar M, et al. (November 2006). "Efficacy of intracoronary nicardipine in the treatment of no-reflow during percutaneous coronary intervention". Catheterization and Cardiovascular Interventions. 68 (5): 671–676. doi:10.1002/ccd.20885. PMID 17034064. S2CID 37071966.
2. Freeman BS (2014). "Vasodilators". In Freeman BS, Berger JS (eds.). Anesthesiology Core Review: Part One Basic Exam. McGraw Hill. ISBN 978-0-07-182137-7.
3. Sutters M (2022). "Hypertensive urgencies & emergencies.". In Papadakis MA, McPhee SJ, Rabow MW, McQuaid KR (eds.). Current Medical Diagnosis & Treatment. McGraw Hill. ISBN 978-1-2642-6938-9.
4. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 464. ISBN 978-3-527-60749-5.
5. "Nicardipine". Medline Plus. U.S. National Library of Medicine.