Nifedipine

Nifedipine
Clinical data
Pronunciation/nəˈfɛdəpin/ nə-FEH-də-peen
Trade namesAdalat, Procardia, others
AHFS/Drugs.comMonograph
MedlinePlusa684028
License data
Pregnancy
category
Routes of
administration		By mouth, topical
Drug classCalcium channel blocker (dihydropyridine)[2]
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability45-56%
Protein binding92-98%
MetabolismGastrointestinal, Liver
Elimination half-life2 hours
ExcretionKidneys: >50%, bile duct: 5-15%
Identifiers
IUPAC name
  • 3,5-dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.040.529
Chemical and physical data
FormulaC17H18N2O6
Molar mass346.339 g·mol−1
3D model (JSmol)
Melting point173 °C (343 °F)
SMILES
  • O=C(OC)\C1=C(\N/C(=C(/C(=O)OC)C1c2ccccc2[N+]([O-])=O)C)C
InChI
  • InChI=1S/C17H18N2O6/c1-9-13(16(20)24-3)15(14(10(2)18-9)17(21)25-4)11-7-5-6-8-12(11)19(22)23/h5-8,15,18H,1-4H3 Y
  • Key:HYIMSNHJOBLJNT-UHFFFAOYSA-N Y
  (verify)

Nifedipine (/nəˈfɛdəpin/ nə-FEH-də-peen), sold under the brand name Procardia among others, is a calcium channel blocker medication used to manage angina, high blood pressure, Raynaud's phenomenon, and premature labor.[2] It is one of the treatments of choice for Prinzmetal angina.[2] It may be used to treat severe high blood pressure in pregnancy.[2] Its use in preterm labor may allow more time for steroids to improve the baby's lung function and provide time for transfer of the mother to a well-qualified medical facility before delivery.[2] It is a calcium channel blocker of the dihydropyridine type.[2] Nifedipine is taken by mouth and comes in fast- and slow-release formulations.[2]

Common side effects include lightheadedness, headache, feeling tired, leg swelling, cough, and shortness of breath.[2] Serious side effects may include low blood pressure and heart failure.[2] Nifedipine is considered safe in pregnancy and breastfeeding.[4]

Nifedipine was patented in 1967 and approved for use in the United States in 1981.[2][5][6] It is on the World Health Organization's List of Essential Medicines.[7] It is available as a generic medication.[2] In 2022, it was the 151st most commonly prescribed medication in the United States, with more than 3 million prescriptions.[8][9]

  1. ^ "Nifedipine Pregnancy and Breastfeeding Warnings". Archived from the original on 21 December 2015. Retrieved 25 December 2015.
  2. ^ a b c d e f g h i j k "Nifedipine". The American Society of Health-System Pharmacists. Archived from the original on 8 August 2018. Retrieved 17 September 2019.
  3. ^ "Product monograph brand safety updates". Health Canada. February 2024. Retrieved 24 March 2024.
  4. ^ "Nifedipine". Drugs and Lactation Database. Bethesda (MD): National Institute of Child Health and Human Development. 15 August 2023. PMID 30000106. Retrieved 14 October 2023.
  5. ^ Sliskovic DR (2013). "Cardiovascular Drugs". In Li JJ, Corey EJ (eds.). Drug Discovery: Practices, Processes, and Perspectives. Hoboken, NJ: John Wiley & Sons. pp. 141–204. ISBN 9781118354469. Archived from the original on 1 September 2017. Retrieved 20 January 2022. p. 172: nifedipine...1,4-dihydropyrine originally approved in 1981.
  6. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 464. ISBN 9783527607495.
  7. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  8. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  9. ^ "Nifedipine Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
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