Verapamil

Verapamil
Clinical data

Pronunciation	/vɜːrˈæpəmɪl/
Trade names	various
AHFS/Drugs.com	Monograph
License data	US FDA: Verapamil
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	by mouth, intravenous
ATC code	C08DA01 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	35.1%
Metabolism	liver
Biological 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-prop-2-ylpentanenitrile
CAS Number	52-53-9^Y
PubChem CID	2520
IUPHAR/BPS	2406
DrugBank	DB00661^Y
ChemSpider	2425^Y
UNII	CJ0O37KU29
KEGG	D02356^Y
ChEBI	CHEBI:9948^Y
ChEMBL	CHEMBL6966^Y
ECHA InfoCard	100.000.133
Chemical and physical data
Formula	C₂₇H₃₈N₂O₄
Molar mass	454.602 g/mol
3D model (Jmol)	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^Y Key:SGTNSNPWRIOYBX-UHFFFAOYSA-N^Y

Verapamil, sold under various trade names, is a medication used for the treatment of high blood pressure, 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 baby 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, the most effective and safe medicines needed in a health system. Verapamil is available as a generic medication. The wholesale cost in the developing world is about 1.71 to 2.70 USD per month. In the United States a month of treatment costs 25 to 50 USD. Long acting formulations exist.

Verapamil is used for controlling ventricular rate in supraventricular tachycardia and migraine headache prevention. It is a class-IV antiarrhythmic and more effective than digoxin in controlling ventricular rate. Verapamil is not listed as a first line agent by the guidelines provided by JAMA in JNC-8. However, it may be used to treat hypertension if patient has co-morbid atrial fibrillation or other types of arrhythmia.

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Wikipedia