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• W2086282990 startingPage "2816" @default.
• W2086282990 abstract "In humans, metabolism of the commonly used nonsteroidal antiinflammatory drug diclofenac 1 yields principally the 4'-hydroxy 2, 5-hydroxy 3, and acyl glucuronide 4 metabolites. All three metabolites have been implicated in rare idiosyncratic adverse reactions associated with this widely used drug. Therefore, for mechanistic toxicological studies of 1, substantial quantities of 2-4 are required and their syntheses and characterization are described here. Key steps were a convenient two-step preparation of aniline 5 from phenol, efficient and selective 6-iodination of amide 18, and high-yielding Ullmann couplings to generate diarylamines 11 and 21. The acyl glucuronide 4 was obtained by Mitsunobu reaction of 1 (free acid) with allyl glucuronate 23 followed by Pd(0) deprotection, using a modification of a published procedure. We report full characterization of 4 and note that this important metabolite has been made available pure and in quantity for the first time. We report also the metabolic fates of the synthetic metabolites: 2 and 3 were glucuronidated in rats, but only 3 formed glutathione adducts in vivo and by enzymatic synthesis via a quinoneimine intermediate. A previously undescribed glutathione adduct of 3 was obtained by enzymatic synthesis. Compound 4 formed an imine-linked protein conjugate as evinced by sodium cyanoborohydride trapping." @default.
• W2086282990 created "2016-06-24" @default.
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• W2086282990 date "2004-04-27" @default.
• W2086282990 modified "2023-10-07" @default.
• W2086282990 title "Syntheses and Characterization of the Acyl Glucuronide and Hydroxy Metabolites of Diclofenac" @default.
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• W2086282990 doi "https://doi.org/10.1021/jm030891w" @default.
• W2086282990 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/15139759" @default.
• W2086282990 hasPublicationYear "2004" @default.
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