Модекаинид

What is this

Modecainide is 4-hydroxy-3-methoxy-N-[2-[2-(1-methyl-2-piperidinyl)ethyl]phenyl]benzamide, the main metabolite of the antiarrhythmic encainide. It was developed under the codes MJ 14030 and BMY 40327, and is found in the literature as 3-methoxy-O-desmethylencainide. Supplied as a racemate.

Identification

• CAS No.: 81329-71-7
• Chemical formula: C22H28N2O3
• Compound class: substituted benzamide, tertiary amine of the piperidine series

Pharmacological group and mechanism

Antiarrhythmic drug. Enkainide belongs to class Ic according to the Vaughan Williams classification: such substances block fast sodium channels of cardiomyocytes and slow down impulse conduction, having little effect on the duration of the action potential. Modecainide is formed in the body during the metabolism of encainide and has comparable intrinsic antiarrhythmic activity, and in terms of slowing conduction in the atria, atrioventricular node and His-Purkinje system it is 4-15 times superior to the original substance. The half-life of the metabolite is longer than that of encainide; it is detected in the plasma of patients after taking encainide orally.

Status and purpose

• was not produced as an independent drug: development was stopped due to frequent proarrhythmogenic effects
• treated as reference standard and research compound
• tasks: analytical identification and quantitative determination of encainide metabolites using HPLC and LC-MS methods, pharmacokinetic and electrophysiological work

Storage and handling

Pharmaceutical substance for research purposes. The container is tightly closed, the place is dry and dark, work with hangers in a fume hood using gloves and safety glasses. Use outside laboratory research is not intended.