Verapamil

Verapamil
Clinical data
Pronunciation/vɛˈræpəmɪl/
ve-RAP-ə-mil
Trade namesIsoptin, Calan, others[1]
AHFS/Drugs.comMonograph
MedlinePlusa684030
License data
Pregnancy
category
Routes of
administration		By mouth, intravenous
Drug classCalcium channel blocker
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability35.1%
MetabolismLiver
Onset of action1 to 2 hours (oral); 3 to 5 minutes (IV bolus)[6][7]
Elimination half-life2.8–7.4 hours[8]
ExcretionKidney: 11%
Identifiers
  • (RS)-2-(3,4-Dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.133 Edit this at Wikidata
Chemical and physical data
FormulaC27H38N2O4
Molar mass454.611 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • N#CC(c1cc(OC)c(OC)cc1)(CCCN(CCc2ccc(OC)c(OC)c2)C)C(C)C
  • 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 checkY
  • Key:SGTNSNPWRIOYBX-UHFFFAOYSA-N checkY
  (verify)

Verapamil, sold under various trade names,[1] 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.[9] It may also be used for the prevention of migraines and cluster headaches.[10][11] It is given by mouth or by injection into a vein.[9]

Common side effects include headache, low blood pressure, nausea, and constipation.[9] Other side effects include allergic reactions and muscle pains.[12] It is not recommended in people with a slow heart rate or heart failure.[12] It is believed to cause problems for the fetus if used during pregnancy.[2] It is in the non–dihydropyridine calcium channel blocker family of medications.[9]

Verapamil was approved for medical use in the United States in 1981.[9][13] It is on the World Health Organization's List of Essential Medicines.[14][15] Verapamil is available as a generic medication.[9] Long acting formulations exist.[12] In 2022, it was the 188th most commonly prescribed medication in the United States, with more than 2 million prescriptions.[16][17]

  1. ^ a b "Verapamil". www.drugs.com. Archived from the original on 1 August 2017. Retrieved 14 December 2016.
  2. ^ a b "Verapamil Use During Pregnancy". Drugs.com. 18 November 2019. Archived from the original on 30 October 2024. Retrieved 26 March 2020.
  3. ^ "Securon SR - Summary of Product Characteristics (SmPC)". (emc). 17 May 2017. Archived from the original on 26 March 2020. Retrieved 26 March 2020.
  4. ^ Cite error: The named reference Calan FDA label was invoked but never defined (see the help page).
  5. ^ Human Medicines Evaluation Division (14 October 2020). "Active substance(s): verapamil". List of nationally authorised medicinal products. European Medicines Agency. Archived from the original (PDF) on 30 October 2024.
  6. ^ Cite error: The named reference medicine-dosage was invoked but never defined (see the help page).
  7. ^ Cite error: The named reference pmid346345 was invoked but never defined (see the help page).
  8. ^ Schroeder JS, Frishman WH, Parker JD, et al. (2013). "Pharmacologic Options for Treatment of Ischemic Disease". Cardiovascular Therapeutics: A Companion to Braunwald's Heart Disease. Elsevier. pp. 83–130. doi:10.1016/b978-1-4557-0101-8.00007-2. ISBN 978-1-4557-0101-8. The elimination half-life of standard verapamil tablets is usually 3 to 7 hours,...
  9. ^ a b c d e f "Verapamil Hydrochloride". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016.
  10. ^ Tfelt-Hansen PC, Jensen RH (July 2012). "Management of cluster headache". CNS Drugs. 26 (7): 571–580. doi:10.2165/11632850-000000000-00000. PMID 22650381. S2CID 22522914.
  11. ^ Merison K, Jacobs H (November 2016). "Diagnosis and Treatment of Childhood Migraine". Current Treatment Options in Neurology. 18 (11): 48. doi:10.1007/s11940-016-0431-4. PMID 27704257. S2CID 28302667.
  12. ^ a b c World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. hdl:10665/44053. ISBN 9789241547659.
  13. ^ "Isoptin: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Archived from the original on 30 October 2024. Retrieved 26 March 2020.
  14. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  15. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  16. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  17. ^ "Verapamil Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.