Disopyramide

Disopyramide
Clinical data
Trade names	Norpace
AHFS/Drugs.com	Monograph
MedlinePlus	a682408
Pregnancy; category	AU: B2;
Routes of; administration	Oral, intravenous
ATC code	C01BA03 (WHO) ;
Legal status
Legal status	BR: Class C1 (Other controlled substances); UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	High
Protein binding	50% to 65%; (concentration-dependent)
Metabolism	Hepatic (CYP3A4-mediated)
Elimination half-life	6.7 hours (range 4 to 10 hours)
Excretion	Renal (80%)
Identifiers
	IUPAC name (RS)-4-(Diisopropylamino)-2-phenyl-2-(pyridin-2-yl)butanamide;
CAS Number	3737-09-5 ;
PubChem CID	3114;
IUPHAR/BPS	7167;
DrugBank	DB00280 ;
ChemSpider	3002 ;
UNII	GFO928U8MQ;
KEGG	D00303 ;
ChEBI	CHEBI:4657 ;
ChEMBL	ChEMBL517 ;
CompTox Dashboard (EPA)	DTXSID1045536 ;
ECHA InfoCard	100.021.010
Chemical and physical data
Formula	C21H29N3O
Molar mass	339.483 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	94.5 to 95 °C (202.1 to 203.0 °F)
	SMILES O=C(N)C(c1ncccc1)(c2ccccc2)CCN(C(C)C)C(C)C;
	InChI 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) ; Key:UVTNFZQICZKOEM-UHFFFAOYSA-N ;
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Disopyramide (INN, trade names Norpace and Rythmodan) is an antiarrhythmic medication used in the treatment of ventricular tachycardia. It is a sodium channel blocker and is classified as a Class 1a anti-arrhythmic agent. Disopyramide has a negative inotropic effect on the ventricular myocardium, significantly decreasing the contractility. 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. 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.