Biotransformation of methyl 5-cyclopropylcarbonyl-2-benzimidazolecarbamate (ciclobendazole) in rats and dogs

Drug Metab Dispos. 1978 Sep-Oct;6(5):518-27.

Abstract

A major metabolite of ciclobendazole (methyl 5-cyclopropylcarbonyl-2-benzimidazolecarbamate) excreted in the urine, bile, and feces of rats was methyl 5-cyclopropylcarbonyl-6-hydroxy-benzimidazolecarbamate, established by comparison of the proton magnetic resonance and mass spectra with that of the authentic compound. This compound represented 8.2% and 7.1% of the dose, respectively, in extracts of 24-hr urine and 48-hr feces samples of rats, but was only a minor metabolite in dog urine (1% of the dose). The unchanged drug was only detected in dog feces, the major route of excretion of radioactivity in the dog. 5-Cyclopropylcarbonyl-2-amino-benzimidazole was present in rat urine (2.5% of the dose). A major metabolite in dog bile was probably 5-cyclopropylcarbinol-2-aminobenzimidazole, formed by loss of the methoxycarbonyl group and reduction of the carbonyl function in the 5-position.

MeSH terms

  • Animals
  • Anthelmintics / metabolism*
  • Anthelmintics / urine
  • Benzimidazoles / metabolism*
  • Benzimidazoles / urine
  • Bile / metabolism
  • Biotransformation
  • Chromatography, High Pressure Liquid
  • Chromatography, Thin Layer
  • Cyclopropanes / metabolism*
  • Cyclopropanes / urine
  • Dogs
  • Feces / analysis
  • Hydrolysis
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Rats

Substances

  • Anthelmintics
  • Benzimidazoles
  • Cyclopropanes