Isolation and Characterization of Human Urinary Metabolites of Meclomen

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The principal metabolites of meclomen (sodium meclofenamate; sodium 2-[(2,6-dichloro-3-methylphenyl)]aminobenzoate monohydrate) were isolated from human urine and characterized by gas chromatography-mass spectrometry (GC-MS) and proton nuclear magnetic resonance (^1H-NMR) spectroscopy together with the Folin-Ciocalteu test. Oxidation occurred at the methyl group at C-3 and/or the aromatic ring in meclomen, yielding the methylol (M-1), dicarboxylic acid (M-2), phenols (M-3 and M-4), 3-hydroxymethylated phenol (M-7), 3-demethylated phenol (M-6) and phenolic dicarboxylic acid (M-8).Among these metabolites, M-1,M-2,M-3 and M-4 are common to fenamate antiinflammatory analgesics. A novel metabolite, M-6,is presumably produced from M-8 through M-7 or M-2 as an intermediate.

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