Encainide

Encainide
Clinical data
Trade names	Enkaid
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a605040
ATC code	C01BC08 (WHO) ;
Legal status
Legal status	Withdrawn;
Identifiers
	IUPAC name 4-Methoxy-N-[2-(1-methyl-2-piperidin-1-ylethyl)phenyl]benzamide;
CAS Number	66778-36-7 ;
PubChem CID	48041;
DrugBank	DB01228 ;
ChemSpider	43697 ;
UNII	SY3J0147NB;
KEGG	D07894 ;
ChEBI	CHEBI:4788 ;
ChEMBL	ChEMBL315838 ;
CompTox Dashboard (EPA)	DTXSID0022983 ;
Chemical and physical data
Formula	C22H28N2O2
Molar mass	352.47 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN1CCCCC1CCC2=CC=CC=C2NC(=O)C3=CC=C(C=C3)OC;
	InChI InChI=1S/C22H28N2O2/c1-24-16-6-5-8-19(24)13-10-17-7-3-4-9-21(17)23-22(25)18-11-14-20(26-2)15-12-18/h3-4,7,9,11-12,14-15,19H,5-6,8,10,13,16H2,1-2H3,(H,23,25) ; Key:PJWPNDMDCLXCOM-UHFFFAOYSA-N ;
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Encainide (trade name Enkaid) is a class Ic antiarrhythmic agent. It is no longer used because of its frequent proarrhythmic side effects.[1]

Synthesis

Encainide synthesis:[2][3][4]

Echt, D. S.; Liebson, P. R.; Mitchell, L. B.; Peters, R. W.; Obias-Manno, D.; Barker, A. H.; Arensberg, D.; Baker, A.; Friedman, L.; Greene, H. L.; Huther, M. L.; Richardson, D. W. (1991). "Mortality and Morbidity in Patients Receiving Encainide, Flecainide, or Placebo". New England Journal of Medicine. 324 (12): 781–788. doi:10.1056/NEJM199103213241201. PMID 1900101.
S.J. Dykstra, J.L. Minelli, DE 2210154 (1972).
S.J. Dykstra, J.L. Minelli, U.S. Patent 3,931,195 (1976).
Dykstra, Stanley J. (1973). "Lysergic acid and quinidine analogs. 2-(o-Acylaminophenethyl)piperidines". Journal of Medicinal Chemistry. 16 (9): 1015–1020. doi:10.1021/jm00267a012. PMID 4745503.

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