Nifedipine

Nifedipine
Clinical data
Trade names	Adalat, Procardia, others
AHFS/Drugs.com	Monograph
MedlinePlus	a684028
License data	US DailyMed: Nifedipine;
Pregnancy; category	AU: C; ;
Routes of; administration	By mouth, topical
Drug class	Calcium channel blocker (dihydropyridine)
ATC code	C08CA05 (WHO) ;
Legal status
Legal status	CA: ℞-only; US: WARNINGRx-only;
Pharmacokinetic data
Bioavailability	45-56%
Protein binding	92-98%
Metabolism	Gastrointestinal, Liver
Elimination half-life	2 hours
Excretion	Kidneys: >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	21829-25-4 ;
PubChem CID	4485;
IUPHAR/BPS	2514;
DrugBank	DB01115 ;
ChemSpider	4330 ;
UNII	I9ZF7L6G2L;
KEGG	D00437 ;
ChEBI	CHEBI:7565 ;
ChEMBL	ChEMBL193 ;
CompTox Dashboard (EPA)	DTXSID2025715 ;
ECHA InfoCard	100.040.529
Chemical and physical data
Formula	C17H18N2O6
Molar mass	346.339 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	173 °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 ; Key:HYIMSNHJOBLJNT-UHFFFAOYSA-N ;
	(verify)

Nifedipine, 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.^[5]

Nifedipine was patented in 1967, and approved for use in the United States in 1981.^[2]^[6]^[7] It is on the World Health Organization's List of Essential Medicines.^[8] 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.^[9]^[10]

^ "Nifedipine Pregnancy and Breastfeeding Warnings". Archived from the original on 21 December 2015. Retrieved 25 December 2015.
^ ^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.
^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
^ "Product monograph brand safety updates". Health Canada. February 2024. Retrieved 24 March 2024.
^ "Nifedipine". Drugs and Lactation Database. Bethesda (MD): National Institute of Child Health and Human Development. 15 August 2023. PMID 30000106. Retrieved 14 October 2023.
^ 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.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 464. ISBN 9783527607495.
^ 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.
^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
^ "Nifedipine Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.

[Drugs.com_pregnancy-1] "Nifedipine Pregnancy and Breastfeeding Warnings". Archived from the original on 21 December 2015. Retrieved 25 December 2015.

[AHFS2015-2] ^ ^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.

[FDA-AllBoxedWarnings-3] "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.

[4] "Product monograph brand safety updates". Health Canada. February 2024. Retrieved 24 March 2024.

[NICHHD_2023-5] "Nifedipine". Drugs and Lactation Database. Bethesda (MD): National Institute of Child Health and Human Development. 15 August 2023. PMID 30000106. Retrieved 14 October 2023.

[6] 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.

[7] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 464. ISBN 9783527607495.

[WHO23rd-8] 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.

[9] "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.

[10] "Nifedipine Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.

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Nifedipine

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