In vitro biotransformation of the analgesic agent, RWJ-51784, in rat, dog and human

Eur J Drug Metab Pharmacokinet. 2003 Apr-Jun;28(2):107-11. doi: 10.1007/BF03190497.

Abstract

RWJ-51784, an analogue of phenyl isoindoles, is a new analgesic agent. The in vitro metabolism of RWJ-51784 was conducted using rat, dog and human hepatic S9 in the presence of an NADPH generating system, and API-ionspray-MS and MS/MS techniques for the metabolite profiling and identification. Unchanged RWJ-51784 (82, 80 & 86% of the sample in rat, dog & human, respectively) plus 6 metabolites were profiled and tentatively identified on the basis of MS data. RWJ-51784 metabolites were formed via the following 3 metabolic pathways: 1. N-demethylation, 2. phenylhydroxylation, and 3. isoindole-oxidation. Pathway 1 produced a moderate or minor metabolite, N-desmethyl-RWJ-51784 (M1; 6% in rat; 5% in dog, 2% in human). Pathway 2 formed 4-hydroxyphenyl-RWJ-51784 (M2; 3-6% in all species). Step 3 formed 2 isoindole-oxidized metaboliotes, OH-indole (M3; 7-8% in all species) and oxo-indole (M4; <1% in all species)-RWJ-51784, and in conjunction with pathway 2 produced 2 trace metabolites, OH-phenyl-OH-isoindole (M5) and OH-phenyl-oxo-isoindole (M6) metabolites. RWJ-51784 is not extensively metabolized in rat, dog and human hepatic S9 fractions.

MeSH terms

  • Analgesics / chemistry*
  • Analgesics / metabolism*
  • Animals
  • Biotransformation / physiology
  • Carbazoles / chemistry
  • Carbazoles / metabolism*
  • Dogs
  • Humans
  • Liver / metabolism*
  • Male
  • Pyrroles / chemistry
  • Pyrroles / metabolism*
  • Rats

Substances

  • 2-methyl-1,2,3,3a,4,5,6,10c-octahydropyrrolo(3,4-c)carbazole
  • Analgesics
  • Carbazoles
  • Pyrroles