Verapamil

Verapamil
Clinical data
Pronunciation	/vɛˈræpəmɪl/; ve-RAP-ə-mil
Trade names	Isoptin, Calan, others
AHFS/Drugs.com	Monograph
MedlinePlus	a684030
License data	EU EMA: by INN; US DailyMed: Verapamil; US FDA: Verapamil;
Pregnancy; category	AU: C;
Routes of; administration	By mouth, intravenous
Drug class	Calcium channel blocker
ATC code	C08DA01 (WHO) ;
Legal status
Legal status	UK: POM (Prescription only); US: ℞-only; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	35.1%
Metabolism	liver
Elimination half-life	2.8–7.4 hours
Excretion	kidney: 11%
Identifiers
	IUPAC name (RS)-2-(3,4-Dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile;
CAS Number	52-53-9 ;
PubChem CID	2520;
IUPHAR/BPS	2406;
DrugBank	DB00661 ;
ChemSpider	2425 ;
UNII	CJ0O37KU29;
KEGG	D02356 ; as HCl: D00619 ;
ChEBI	CHEBI:9948 ;
ChEMBL	ChEMBL6966 ;
CompTox Dashboard (EPA)	DTXSID9041152 ;
ECHA InfoCard	100.000.133
Chemical and physical data
Formula	C27H38N2O4
Molar mass	454.611 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
	SMILES N#CC(c1cc(OC)c(OC)cc1)(CCCN(CCc2ccc(OC)c(OC)c2)C)C(C)C;
	InChI InChI=1S/C27H38N2O4/c1-20(2)27(19-28,22-10-12-24(31-5)26(18-22)33-7)14-8-15-29(3)16-13-21-9-11-23(30-4)25(17-21)32-6/h9-12,17-18,20H,8,13-16H2,1-7H3 ; Key:SGTNSNPWRIOYBX-UHFFFAOYSA-N ;
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Verapamil, sold under various trade names, is a calcium channel blocker medication used for the treatment of high blood pressure, angina (chest pain from not enough blood flow to the heart), and supraventricular tachycardia. It may also be used for the prevention of migraines and cluster headaches. It is given by mouth or by injection into a vein.

Common side effects include headache, low blood pressure, nausea, and constipation. Other side effects include allergic reactions and muscle pains. It is not recommended in people with a slow heart rate or heart failure. It is believed to cause problems for the fetus if used during pregnancy. It is in the non–dihydropyridine calcium channel blocker family of medications.

Verapamil was approved for medical use in the United States in 1981. It is on the World Health Organization's List of Essential Medicines. Verapamil is available as a generic medication. Long acting formulations exist. In 2020, it was the 151st most commonly prescribed medication in the United States, with more than 3 million prescriptions.

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