Abstract
Bovine kidney and liver homogenates degraded a cysteine conjugate of methazolamide, S‐(5‐acetylimino‐4‐methyl‐Δ2‐1,3,4‐thiadiazolin‐2‐yl)cysteine. We isolated the degradation product following incubation with kidney homogenate by high‐performance liquid chromatography on reversed‐phase columns. The chemical structure was confirmed by proton and carbon‐13 nuclear magnetic resonance spectroscopy (1H NMR and 13C NMR, respectively), and elemental analysis by high‐resolution mass spectrometry to be N‐(3‐methyl‐5‐mercapto‐Δ4‐1,3,4‐thiadiazol‐2‐yl)acetamide, a thiol compound. The reaction is thought to be catalyzed by a pyridoxal‐dependent enzyme(s) as indicated by an inhibition study using aminooxyacetic acid. Possible involvement of the thiol compound in the development of an adverse effect is discussed. © 2001 Wiley‐Liss, Inc. and the American Pharmaceutical Association J Pharm Sci 90:224–233, 2001
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