Genetically determined stereoselective excretion of encainide in humans and electrophysiologic effects of its enantiomers in canine cardiac Purkinje fibers

Clin Pharmacol Ther. 1991 May;49(5):488-96. doi: 10.1038/clpt.1991.59.

Abstract

Encainide metabolism is mediated by the polymorphically distributed cytochrome P450IID6, which displays stereoselectivity for some substrates. In this study we found that urinary recovery during steady-state encainide in three poor metabolizers was high (49% to 80%), consisted mainly of unchanged encainide, was nonstereoselective (+/- ratio, 0.985 to 1.049), and was unchanged by quinidine, a potent inhibitor of P450IID6. In contrast, in seven extensive metabolizers the +/- urinary ratios were 1.20 +/- 0.06 for encainide and 0.81 +/- 0.06 (both p less than 0.01) for the cytochrome P450IID6 products O-desmethylencainide plus 3-methoxy-O-desmethylencainide; with quinidine the total percentage recovery rose from 4% +/- 4% to 37% +/- 9% because of increased recovery of unchanged encainide and became non-stereoselective (+/- ratio, 0.84 +/- 0.08 [encainide alone] versus 0.97 +/- 0.05 [encainide plus quinidine]). In vitro, encainide enantiomers depressed the maximum rate of metabolism with similar frequency and concentration dependence. We conclude that (-)-encainide undergoes preferential metabolism by cytochrome P450IID6; however, this genetically determined stereoselective disposition is unlikely to play a major role in mediating the clinical actions of encainide.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Action Potentials / drug effects
  • Anilides / chemistry
  • Anilides / pharmacokinetics
  • Anilides / pharmacology
  • Anilides / urine*
  • Animals
  • Anti-Arrhythmia Agents / chemistry
  • Anti-Arrhythmia Agents / pharmacokinetics
  • Anti-Arrhythmia Agents / pharmacology
  • Anti-Arrhythmia Agents / urine*
  • Cytochrome P-450 Enzyme Inhibitors
  • Cytochrome P-450 Enzyme System / metabolism
  • Dogs
  • Drug Evaluation, Preclinical
  • Drug Interactions
  • Encainide
  • Phenotype
  • Purkinje Fibers / drug effects*
  • Quinidine / pharmacokinetics
  • Quinidine / pharmacology
  • Stereoisomerism

Substances

  • Anilides
  • Anti-Arrhythmia Agents
  • Cytochrome P-450 Enzyme Inhibitors
  • Cytochrome P-450 Enzyme System
  • Quinidine
  • Encainide