Metabolism and disposition of the metabotropic glutamate receptor 5 antagonist (mGluR5) mavoglurant (AFQ056) in healthy subjects

Drug Metab Dispos. 2013 Sep;41(9):1626-41. doi: 10.1124/dmd.112.050716. Epub 2013 Jun 17.

Abstract

The disposition and biotransformation of (14)C-radiolabeled mavoglurant were investigated in four healthy male subjects after a single oral dose of 200 mg. Blood, plasma, urine, and feces collected over 7 days were analyzed for total radioactivity, mavoglurant was quantified in plasma by liquid chromatography coupled to tandem mass spectrometry (LC-MS/MS), and metabolite profiles were generated in plasma and excreta by high-performance liquid chromatography (HPLC) and radioactivity detection. The chemical structures of mavoglurant metabolites were characterized by LC-MS/MS, wet-chemical and enzymatic methods, NMR spectroscopy, and comparison with reference compounds. Mavoglurant was safe and well tolerated in this study population. Mavoglurant absorption was ≥50% of dose reaching mean plasma Cmax values of 140 ng/ml (mavoglurant) and 855 ng-eq/ml (total radioactivity) at 2.5 and 3.6 hours, respectively. Thereafter, mavoglurant and total radioactivity concentrations declined with mean apparent half-lives of 12 and 18 hours, respectively. The elimination of mavoglurant occurred predominantly by oxidative metabolism involving primarily 1) oxidation of the tolyl-methyl group to a benzyl-alcohol metabolite (M7) and subsequently to a benzoic acid metabolite (M6), and 2) oxidation of the phenyl-ring leading to a hydroxylated metabolite (M3). The subjects were mainly exposed to mavoglurant and seven main metabolites, which combined accounted for 60% of (14)C-AUC0-72 h (area under the concentration-time curve from time 0 to infinity). The primary steps of mavoglurant metabolism observed in vivo could partially be reproduced in vitro in incubations with human liver microsomes and recombinant cytochrome P450 enzymes. After 7 days, the mean balance of total radioactivity excretion was almost complete (95.3% of dose) with 36.7% recovered in urine and 58.6% in feces.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Absorption
  • Adult
  • Area Under Curve
  • Carbon Radioisotopes / blood
  • Carbon Radioisotopes / metabolism
  • Carbon Radioisotopes / pharmacokinetics
  • Carbon Radioisotopes / urine
  • Cytochrome P-450 Enzyme System / metabolism
  • Feces / chemistry
  • Half-Life
  • Humans
  • Indoles / blood
  • Indoles / metabolism*
  • Indoles / pharmacokinetics*
  • Indoles / urine
  • Male
  • Microsomes, Liver / enzymology
  • Microsomes, Liver / metabolism
  • Oxidation-Reduction
  • Receptor, Metabotropic Glutamate 5 / antagonists & inhibitors*
  • Receptor, Metabotropic Glutamate 5 / metabolism*

Substances

  • Carbon Radioisotopes
  • GRM5 protein, human
  • Indoles
  • Receptor, Metabotropic Glutamate 5
  • Cytochrome P-450 Enzyme System
  • mavoglurant