RT Journal Article
SR Electronic
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
FD American Society for Pharmacology and Experimental Therapeutics
SP 694
OP 696
DO 10.1124/dmd.31.6.694
VO 31
IS 6
A1 Iain J. Martin
A1 Richard J. Lewis
A1 Roger V. Bonnert
A1 Peter Cage
A1 Graeme C. Moody
YR 2003
UL http://dmd.aspetjournals.org/content/31/6/694.abstract
AB 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