Nicardipine

Summary

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 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
  • 55985-32-5 checkY
PubChem CID
  • 4474
IUPHAR/BPS
  • 2559
DrugBank
  • DB00622 checkY
ChemSpider
  • 4319 checkY
UNII
  • CZ5312222S
KEGG
  • D08270 checkY
ChEBI
  • CHEBI:7550
ChEMBL
  • ChEMBL1484 checkY
CompTox Dashboard (EPA)
  • DTXSID6023363 Edit this at Wikidata
ECHA InfoCard100.054.466 Edit this at Wikidata
Chemical and physical data
FormulaC26H29N3O6
Molar mass479.533 g·mol−1
3D model (JSmol)
  • Interactive image
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)

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 edit

References edit

  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. ^ 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.
  3. ^ 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.
  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.