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Nicardipine

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
  • 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 Edit this at Wikidata
Chemical and physical data
FormulaC26H29N3O6
Molar mass479.533 g·mol−1
3D model (JSmol)
Melting point136–138 °C (277–280 °F)
  • O=C(OCCN(Cc1ccccc1)C)\C2=C(\N/C(=C(/C(=O)OC)C2c3cccc([N+]([O-])=O)c3)C)C
  • 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 checkY
  • Key:ZBBHBTPTTSWHBA-UHFFFAOYSA-N checkY
  (verify)

Nicardipine (Cardene) is a medication used to treat angina and hypertension, especially for hemorrhagic stroke patients.[1] 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.[2]

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.[3][4] As its use may lead to reflex tachycardia, it is advisable to use it in conjunction with a beta-blocker.[4][3] In the setting of a ruptured brain aneurysm, nicardipine may be used (if nimodipine is unavailable) to reduce blood pressure and as prevention or treatment against cerebral vasospasm.[1]

It was patented in 1973 and approved for medical use in 1981.[5] Nicardipine was approved by the FDA in December 1988. The patent for both Cardene and Cardene SR expired in October 1995.[6]

  1. ^ a b Hemphill JC, Smith WS, Gress DR (2022). "Chapter 429: Subarachnoid Hemorrhage". Harrison's Principles of Internal Medicine (21st ed.). New York: McGraw Hill. ISBN 978-1-264-26850-4.
  2. ^ 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.
  3. ^ a b 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.
  4. ^ a b 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.
  5. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 464. ISBN 978-3-527-60749-5.
  6. ^ "Nicardipine". Medline Plus. U.S. National Library of Medicine.
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