The structure of the glucuronide of sulphadimethoxine formed in man

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Abstract
The major metabolite of 2,4-dimethoxy-6-sulphanilamidopyrimidine (sulphadimethoxine) in urine in man is a non-reducing glucuronide, which has been isolated and characterized as its S-benzylthiouronium salt. The same compound was made synthetically by standard methods from sodium sulphadimethoxine and methyl 2,3,4-tri-O-acetyl-1-bromoglucuronate. On hydrolysis with acid, the glucuronide yielded sulphanilic acid, glucuronic acid and barbituric acid, and with [beta]-glucuronidase it slowly yielded sulphadimethoxine and glucuronic acid. Evidence based on infrared spectra and other data showed that the urinary and synthetic glucuronide was l-deoxy-l-[N1[image]-(2[image],4[image]-dimethoxypyrimidin-6[image]-yl) sulphanialamido-[beta]-D-glucosid]uronic acid or sulphadimethoxine N1-glucuronide. N1-Methyl- and Nring- methyl derivatives of sulphadimethoxine and 4-methoxy-6-sulphanilamidopyrimidine were prepared and their infrared and ultraviolet spectra determined for comparison.