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• W2098996875 startingPage "1502" @default.
• W2098996875 abstract "The glucuronidation of (1S,2R,3R,5R)-3-(hydroxymethyl)-5-[7-{[(1R,2S)-2-phenylcyclopropyl]amino}-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl]cyclopentane-1,2-diol (AZ11939714) was studied in UDP-glucuronic acid (UDPGA)-supplemented hepatic microsomes from rat, dog, and human liver. The major biliary metabolite of this compound after intraduodenal administration to a beagle dog was also studied. The techniques of HPLC, HPLC-MS and HPLC-NMR were used to characterize the glucuronides. An analysis of the proton NMR chemical shift differences between parent and metabolites was sufficient to deduce the sites of glucuronidation, although these were confirmed by 2D ROESY experiments. In dog microsomes, AZ11939714 was O-glucuronidated exclusively at the 1-position of the cyclopentanediol. This glucuronide was also the major metabolite in dog bile. In human microsomes, AZ11939714 was O-glucuronidated almost exclusively at the 3-hydroxymethyl position. Rat microsomes produced a mixture of glucuronides at the 2-position of the cyclopentanediol (major) and at the 3-hydroxymethyl position (minor). A clear qualitative species difference in the glucuronidation of AZ11939714 has been demonstrated in vitro. This may have implications for the choice of laboratory species to study the pharmacokinetics and safety of this compound." @default.
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• W2098996875 date "2006-06-08" @default.
• W2098996875 modified "2023-10-17" @default.
• W2098996875 title "Which Hydroxy? Evidence for Species Differences in the Regioselectivity of Glucuronidation in Rat, Dog, and Human in Vitro Systems and Dog in Vivo" @default.
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• W2098996875 doi "https://doi.org/10.1124/dmd.106.009282" @default.
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