The metabolism of sulphonamides

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Abstract
The extent of acetylation and oxidation in the rabbit of certain N-substituted heterocyclic sulfonamide drugs has been measured. Similar measurements have been made on sulfanilic acid, p-aminobenzoic acid and related compounds. All sulfonamides with pKa''s between 6 and 9 are highly acetylated; compounds with a pKa less than 6 were not highly acetylated. p-Subs-tituted acetanilides are not deacetylated by the rabbit. In some sulfonamides, e.g., sulfamerazine, sulfamezathine and sulfathiazole, oxidation occurs in the free drug but not with the acetylated drug, whereas with sulfapyridine both the acetyl derivative and the free drug are oxidized. Sulfadiazine and sulfapyrazine are not oxidized. Sulfanilic acid is neither acetylated nor oxidized whereas p-aminobenzpic acid is slightly acetylated (c.20%) but not oxidized. The results obtained have been related as far as possible to certain physico-chemical concepts.