Disopyramide

Disopyramide
Clinical data
Trade namesNorpace
AHFS/Drugs.comMonograph
MedlinePlusa682408
Pregnancy
category
  • AU: B2
Routes of
administration		Oral, intravenous
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityHigh
Protein binding50% to 65%
(concentration-dependent)
MetabolismHepatic (CYP3A4-mediated)
Elimination half-life6.7 hours (range 4 to 10 hours)
ExcretionRenal (80%)
Identifiers
  • (RS)-4-(Diisopropylamino)-2-phenyl-2-(pyridin-2-yl)butanamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.021.010 Edit this at Wikidata
Chemical and physical data
FormulaC21H29N3O
Molar mass339.483 g·mol−1
3D model (JSmol)
Melting point94.5 to 95 °C (202.1 to 203.0 °F)
  • O=C(N)C(c1ncccc1)(c2ccccc2)CCN(C(C)C)C(C)C
  • InChI=1S/C21H29N3O/c1-16(2)24(17(3)4)15-13-21(20(22)25,18-10-6-5-7-11-18)19-12-8-9-14-23-19/h5-12,14,16-17H,13,15H2,1-4H3,(H2,22,25) checkY
  • Key:UVTNFZQICZKOEM-UHFFFAOYSA-N checkY
  (verify)

Disopyramide (INN, trade names Norpace and Rythmodan) is an antiarrhythmic medication used in the treatment of ventricular tachycardia.[2] It is a sodium channel blocker and is classified as a Class 1a anti-arrhythmic agent.[3][4] Disopyramide has a negative inotropic effect on the ventricular myocardium, significantly decreasing the contractility.[5][6] Disopyramide also has general anticholinergic effects which contribute to unwanted adverse effects. Disopyramide is available in both oral and intravenous forms. In 1972, when it was one of the only alternatives to quinidine, it was praised for being more potent and somewhat less toxic.[6] However, a 2012 review of antiarrhythmic drugs noted that disopyramide is among the most toxic agents, with a high burden of side effects and increased mortality (compared to placebo) when used to treat atrial fibrillation.[7]

  1. ^ "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control]. Diário Oficial da União [Official Diary of the Union] (in Brazilian Portuguese). Brazilian Health Regulatory Agency (Anvisa) (published 2023-04-04). 2023-03-31. Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ^ Hall JE, Guyton AC (2006). Pocket Companion to Guyton & Hall Textbook of Medical Physiology. Elsevier. ISBN 9788480862325. OCLC 1027935564.
  3. ^ Rizos I, Brachmann J, Lengfelder W, Schmitt C, von Olshausen K, Kübler W, et al. (February 1987). "Effects of intravenous disopyramide and quinidine on normal myocardium and on the characteristics of arrhythmias: intraindividual comparison in patients with sustained ventricular tachycardia". European Heart Journal. 8 (2): 154–163. doi:10.1093/oxfordjournals.eurheartj.a062243. PMID 3569310.
  4. ^ Kim SY, Benowitz NL (1990). "Poisoning due to class IA antiarrhythmic drugs. Quinidine, procainamide and disopyramide". Drug Safety. 5 (6): 393–420. doi:10.2165/00002018-199005060-00002. PMID 2285495. S2CID 71415838.
  5. ^ Levites R, Anderson GJ (September 1979). "Electrophysiological effects of disopyramide phosphate during experimental myocardial ischemia". American Heart Journal. 98 (3): 339–344. doi:10.1016/0002-8703(79)90046-2. PMID 474380.
  6. ^ a b Mathur PP (December 1972). "Cardiovascular effects of a newer antiarrhythmic agent, disopyramide phosphate". American Heart Journal. 84 (6): 764–770. doi:10.1016/0002-8703(72)90069-5. PMID 4150336.
  7. ^ Camm J (2012-03-22). "Antiarrhythmic drugs for the maintenance of sinus rhythm: risks and benefits". Int. J. Cardiol. 155 (3): 362–371. doi:10.1016/j.ijcard.2011.06.012. PMID 21708411. Retrieved 1 May 2024. Compared with controls, patients treated with disopyramide had a significantly higher mortality, with a Peto odds ratio (i.e., pooled odds ratio) of 7.56.