4-Acetamidobenzenesulfonamide (Synonyms: APAS, N-Acetyl p-Aminobenzene Sulfonamide, N4-Acetyl Sulfanilamide, N-Acetylsulfanilamide, NSC 217, NSC 406839)

4-Acetamidobenzenesulfonamide is a metabolite of the herbicide asulam and the sulfonamide antibiotic sulfanilamide .^1,2,3 It is formed from asulam by conversion to sulfanilamide via intestinal microflora, followed by N⁴-acetylation in the liver. 4-Acetamidobenzenesulfonamide inhibits carbonic anhydrase II (CAII), CAIX, and CAXII (K_is = 246, 135, and 49 nM, respectively, for the human enzymes).⁴ It has also been used in the synthesis of compounds with antibacterial activity.⁵

1.Heijbroek, W.M., Muggleton, D.F., and Parke, D.V.Metabolism of the carbamate herbicide, asulam, in the ratXenobiotica14(3)235-247(1984) 2.Okumura, F., Ueda, O., Kitamura, S., et al.N-acetylation and N-formylation of carcinogenic arylamines and related compounds in dogsCarcinogenesis16(1)71-76(1995) 3.Olsen, H., and MØrland, J.Sulfonamide acetylation in isolated rat liver cellsActa Pharmacol. Toxicol. (Copenh)49(2)102-109(1981) 4.Ozensoy, O., Puccetti, L., Fasolis, G., et al.Carbonic anhydrase inhibitors: Inhibition of the tumor-associated isozymes IX and XII with a library of aromatic and heteroaromatic sulfonamidesBioorg. Med. Chem. Lett.15(21)4862-4866(2005) 5.Wang, X.-L., Wan, K., and Zhou, C.-H.Synthesis of novel sulfanilamide-derived 1,2,3-triazoles and their evaluation for antibacterial and antifungal activitiesEur. J. Med. Chem.45(10)4631-4639(2010)