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. 1965 Sep;96(3):829–836. doi: 10.1042/bj0960829

The structure of the glucuronide of sulphadimethoxine formed in man

J W Bridges 1, M R Kibby 1, R T Williams 1
PMCID: PMC1207225  PMID: 5862422

Abstract

1. 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. 2. The same compound was made synthetically by standard methods from sodium sulphadimethoxine and methyl 2,3,4-tri-O-acetyl-1-bromoglucuronate. 3. On hydrolysis with acid, the glucuronide yielded sulphanilic acid, glucuronic acid and barbituric acid, and with β-glucuronidase it slowly yielded sulphadimethoxine and glucuronic acid. 4. Evidence based on infrared spectra and other data showed that the urinary and synthetic glucuronide was 1-deoxy-1-[N1′-(2″,4″-dimethoxypyrimidin-6″ -yl)sulphanilamido-β-d-glucosid]uronic acid or sulphadimethoxine N1-glucuronide. 5. N1-Methyl- and Nring-methyl derivatives of sulphadimethoxine and 4-methoxy-6-sulphanilamidopyrimidine were prepared and their infrared and ultraviolet spectra determined for comparison.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

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