TY - JOUR T1 - NMR IDENTIFICATION OF AN <em>S</em>-LINKED GLUCURONIDE OF A TRIAZOLE THIONE FORMED IN VITRO JF - Drug Metabolism and Disposition JO - Drug Metab Dispos SP - 694 LP - 696 DO - 10.1124/dmd.31.6.694 VL - 31 IS - 6 AU - Iain J. Martin AU - Richard J. Lewis AU - Roger V. Bonnert AU - Peter Cage AU - Graeme C. Moody Y1 - 2003/06/01 UR - http://dmd.aspetjournals.org/content/31/6/694.abstract N2 - The metabolism of 3-{[3-(2-Chlorophenyl)-4,5-dihydro-5-thioxo-1H-1,2,4-triazol-1-yl]methyl}benzonitrile (AR-C133611XX) was studied in isolated dog hepatocytes. The major metabolite of AR-C133611XX was characterized by high performance liquid chromatography-mass spectrometry and NMR and found to be the product of direct glucuronidation. Evidence from 1H and 13C-NMR chemical shifts and a long-range proton carbon correlation experiment was used to deduce that glucuronidation had taken place on the sulfur atom. Full NMR data on this unusual metabolite is presented. Substitution or replacement of the sulfur atom resulted in a significant decrease in the observed rate of glucuronidation. The American Society for Pharmacology and Experimental Therapeutics ER -