New metabolites of the drug 5-aminosalicylic acid. I:N-β-D-glucopyranosyl-5-aminosalicylic acid

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Abstract
1. A new unstable metabolite of 5-aminosalicylic acid (5-ASA) was found in plasma from healthy volunteers dosed with 5-ASAi.v. 2. The metabolite was prepared by incubation of 5-ASA with rat liver homogenate, and isolated using preparative h.p.l.c. 3. The metabolite was identified as N-β-D-glucopyranosyl-5-aminosalicylic acid by n.m.r. spectroscopy and by FAB mass spectrometry. 4. N-β-D-Glucopyranosyl-5-ASA was formed non-enzymically from 5-ASA and glucose in phosphate buffer pH7.4, and was unstable under weakly acidic conditions, decomposition increasing with temperature, i.e. decomposition was complete after 30 min at pH 5.0 and 23°C.