Bioactivation of dapsone to a cytotoxic metabolite by human hepatic microsomal enzymes

Br J Clin Pharmacol. 1989 Oct;28(4):389-95. doi: 10.1111/j.1365-2125.1989.tb03517.x.

Abstract

1. Using human mononuclear leucocytes as target cells, we have investigated the bioactivation of dapsone (DDS) to a cytotoxic metabolite in the presence of microsomes from nine human livers. Values for NADPH dependent toxicity ranged from 8.8-27% (15.8 +/- 5.9%) and were similar to those for microsomes from control mice, 16-24% (19.0 +/- 4.8%). 2. Microsomes prepared from mice induced with either phenobarbitone or beta-naphthoflavone did not produce significantly more NADPH dependent toxicity than microsomes prepared from control mice. 3. Cytotoxicity was abolished not only by ascorbic acid, but also by sub-physiological concentrations of N-acetylcysteine and glutathione. 4. DDS was metabolised in vitro to a hydroxylamine (metabolic conversion 3.1 +/- 1.5%), which was oxidised further to a cytotoxic metabolite which also became irreversibly bound to protein.

MeSH terms

  • Adolescent
  • Adult
  • Biotransformation
  • Cell Survival / drug effects
  • Child
  • Child, Preschool
  • Chromatography, High Pressure Liquid
  • Dapsone / metabolism*
  • Dapsone / pharmacokinetics
  • Dapsone / pharmacology
  • Female
  • Humans
  • In Vitro Techniques
  • Leukocytes, Mononuclear / metabolism*
  • Male
  • Microsomes, Liver / enzymology*
  • Middle Aged
  • NADP / metabolism
  • Trypan Blue

Substances

  • NADP
  • Dapsone
  • Trypan Blue