Species differences in metabolism and pharmacokinetics of a sphingosine-1-phosphate receptor agonist in rats and dogs: formation of a unique glutathione adduct in the rat

Drug Metab Dispos. 2006 Aug;34(8):1367-75. doi: 10.1124/dmd.105.009027. Epub 2006 May 12.

Abstract

The pharmacokinetics and metabolism of 1-(4-((4-phenyl-5-trifluoromethyl-2-thienyl)methoxy)benzyl)azetidine-3-carboxylic acid (MRL-A), a selective agonist for the sphingosine-1-phosphate 1 (S1P1) receptor, were investigated in rats and dogs. In both species, more than 50% of the dose was excreted in bile. Specific to the rat, and observed in bile, were a taurine conjugate of MRL-A and a glucuronide conjugate of an azetidine lactam metabolite. In dogs, a smaller portion of the dose (54% of administered dose) was excreted intact in bile, and the major metabolites detected were an azetidine N-oxide of MRL-A and an acylglucuronide of an N-dealkylation product. This latter metabolite was also observed in rat bile. Stereoselective formation of the N-oxide isomer was observed in dogs, whereas the rat produced comparable amounts of both isomers. The formation of a unique glutathione adduct was observed in rat bile, which was proposed to occur via N-dealkylation, followed by reduction of the putative aldehyde product to form the alcohol, and dehydration of the alcohol to generate a reactive quinone methide intermediate. Incubation of a synthetic standard of this alcohol in rat microsomes fortified with reduced glutathione or rat hepatocytes resulted in formation of this unique glutathione adduct.

Publication types

  • Comparative Study

MeSH terms

  • Administration, Oral
  • Animals
  • Azetidines / administration & dosage
  • Azetidines / pharmacokinetics*
  • Azetidines / urine
  • Bile / chemistry
  • Biotransformation
  • Dogs
  • Feces / chemistry
  • Glutathione / metabolism*
  • Injections, Intravenous
  • Intestinal Mucosa / metabolism
  • Male
  • Protein Binding
  • Rats
  • Rats, Sprague-Dawley
  • Receptors, Lysosphingolipid / agonists*
  • Species Specificity
  • Thiophenes / administration & dosage
  • Thiophenes / pharmacokinetics*
  • Thiophenes / urine

Substances

  • 1-(4-((4-phenyl-5-trifluoromethyl-2-thienyl)methoxy)benzyl)azetidine-3-carboxylic acid
  • Azetidines
  • Receptors, Lysosphingolipid
  • Thiophenes
  • Glutathione