Carbon-Carbon Bond Cleavage Catalyzed by Human Cytochrome P450 Enzymes: a-Ketol as the Key Intermediate Metabolite in Sequential Metabolism of Olanexidine.
Drug metabolism letters(2019)
摘要
3,2-ketol olanexidine and 2,3-ketol olanexidine were confirmed as the key intermediates in carbon-carbon bond cleavage. Its mechanism is proposed that a nucleophilic addition of iron-peroxo species, generated by CYP2D6 and CYP3A4/5, to the carbonyl group caused the carbon-carbon bond cleavage between the adjacent hydroxyl and ketone groups. As results, 2,3-ketol olanexidine formed a C6 side chain acid metabolite. While, 3,2-ketol olanexidine formed a C6 side chain aldehyde intermediate, which was either oxidized to a C6 side chain acid metabolite or reduced to a C6 side chain hydroxyl metabolite.
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关键词
Carbon-Carbon Bond Cleavage,Cytochrome P450 Enzyme,Ketol,Metabolic Pathway,Metabolism,Olanexidine
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