NMR identification of an S-linked glucuronide of a triazole thione formed in vitro
| Autor: | Richard J. Lewis, Peter Cage, Roger Bonnert, Iain J. Martin, Graeme C. Moody |
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| Rok vydání: | 2003 |
| Předmět: |
Male
Magnetic Resonance Spectroscopy Stereochemistry Metabolite Triazole Glucuronidation Pharmaceutical Science chemistry.chemical_element Mass Spectrometry Receptors Interleukin-8B chemistry.chemical_compound Dogs Glucuronides Nitriles Animals Carbon Radioisotopes Cells Cultured Chromatography High Pressure Liquid Pharmacology Chemical shift Nuclear magnetic resonance spectroscopy Triazoles Sulfur Benzonitrile chemistry Hepatocytes Glucuronide |
| Zdroj: | Drug metabolism and disposition: the biological fate of chemicals. 31(6) |
| ISSN: | 0090-9556 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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