Tocainide conjugation in humans: novel biotransformation pathway for a primary amine

J Pharm Sci. 1980 Jan;69(1):47-9. doi: 10.1002/jps.2600690113.

Abstract

The metabolism of tocainide, an experimental antiarrhythmic drug, was studied in humans. Urinary excretion of unchanged drug was 28-55% in 24 hr after oral dosing. Urine hydrolysis with hydrochloric acid or beta-glucuronidase increased tocainide recovery to 55-79%. Saccharo-1,4-lactone inhibited the beta-glucuronidase-mediated tocainide recovery increase. Adjustment of urine to pH 13 produced a compound identified as 3-(2,6-xylyl)-5-methylhydantoin. Evidence suggests that it was derived from the same metabolite that formed the additional tocainide after acid or beta-glucuronidase treatment. Tocainide carbamoyl O-beta-D-glucuronide is the structure proposed for the metabolite. The suggested pathway for its formation involves the addition of carbon dioxide to the amino nitrogen of tocainide followed by uridine diphosphate-glucuronic acid conjugation.

MeSH terms

  • Anilides / metabolism*
  • Anilides / urine
  • Anti-Arrhythmia Agents / metabolism*
  • Anti-Arrhythmia Agents / urine
  • Biotransformation
  • Carbon Dioxide / metabolism
  • Glucuronates / metabolism
  • Glucuronidase / metabolism
  • Humans
  • Hydrolysis

Substances

  • Anilides
  • Anti-Arrhythmia Agents
  • Glucuronates
  • Carbon Dioxide
  • Glucuronidase