A metabolite of asulam and sulfanilamide
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Parent Compound(s)
37902Asulam 23723Sulfanilamide
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4-Acetamidobenzenesulfonamide

Item No. 34689

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[4-(aminosulfonyl)phenyl]-acetamide
CAS Number
121-61-9
Synonyms
  • APAS
  • N-Acetyl p-Aminobenzene Sulfonamide
  • N4-Acetyl Sulfanilamide
  • N-Acetylsulfanilamide
  • NSC 217
  • NSC 406839
Molecular Formula
C8H10N2O3S
Formula Weight
214.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:10): 0.09 mg/ml
λmax
261 nm
SMILES
O=C(C)NC1=CC=C(S(=O)(N)=O)C=C1
InChi Code
InChI=1S/C8H10N2O3S/c1-6(11)10-7-2-4-8(5-3-7)14(9,12)13/h2-5H,1H3,(H,10,11)(H2,9,12,13)
InChi Key
PKOFBDHYTMYVGJ-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    4-Acetamidobenzenesulfonamide is a metabolite of the herbicide asulam and the sulfonamide antibiotic sulfanilamide (Item No. 23723).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 (Kis = 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

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Heijbroek, W.M., Muggleton, D.F., and Parke, D.V. Metabolism of the carbamate herbicide, asulam, in the rat. Xenobiotica 14(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 dogs. Carcinogenesis 16(1), 71-76 (1995).

    3. Olsen, H., and Mørland, J. Sulfonamide acetylation in isolated rat liver cells. Acta 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 sulfonamides. Bioorg. 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 activities. Eur. J. Med. Chem. 45(10), 4631-4639 (2010).