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Spectroscopic analysis demonstrates transacylation and hydrolysis pathways of ibuprofen acyl glucuronides, highlighting reaction kinetics that may drive metabolite toxicity.
Drugs and drug metabolites containing a carboxylic-acid moiety can undergo in vivo conjugation to form 1-β-O-acyl-glucuronides (1-β-O-AGs). In addition to hydrolysis, these conjugates can undergo spontaneous acyl migration, and anomerisation reactions, resulting in a range of positional isomers. Facile transacylation has been suggested as a mechanism contributing to the toxicity of acyl glucuronides, with the kinetics of these processes thought to be a factor. Previous
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Richards et al. (2024) studied this question.
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