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The biotransformation of a sulfonamide to a mercaptan and to mercapturic acid and glucuronide conjugates

1965; Elsevier BV; Volume: 14; Issue: 4 Linguagem: Inglês

10.1016/0006-2952(65)90218-2

1873-2968

D Colucci, D.A. Buyske,

Phosphodiesterase function and regulation

Benzothiazole-2 sulfonamide undergoes complete metabolism by the rat, rabbit, and dog to form three urinary metabolites conclusively identified by u.v. spectra, radiochemical analysis, and paper chromatography with authentic compounds as benzothiazole-2 mercapturic acid, benzothiazole-2 mercaptan, and benzothiazole-2 thioglucuronic acid. These products result from replacement of the sulfonamide by glutathione to form the intermediate tentatively identified as benzothiazole-2 glutathione. This intermediate then undergoes a multiple step reaction including the loss of two of the amino acids of the tripeptide followed by acetylation of the cysteine to form the mercapturic acid conjugate as a major metabolite. A cleavage of a sulfurcarbon bond of the benzothiazole-2 glutathione conjugate (or cysteine derivative) results in formation of a mercaptan group at a point where the sulfonamide was originally attached. Most of this mercaptan forms a thio ester with glucuronic acid before it is excreted in the urine.