A sulfonamide antibiotic and inhibitor of CAII and CAIX
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Sulfanilamide

Item No. 23723

Technical Information
Formal Name
4-amino-benzenesulfonamide
CAS Number
63-74-1
Synonyms
  • 4-Aminobenzenesulfonamide
  • p-Aminobenzenesulfonamide
  • NSC 7618
  • Ro 1-3354
Molecular Formula
C6H8N2O2S
Formula Weight
Purity
≥98%
A solid
DMSO: Slightly SolubleMethanol: Slightly SolubleWater: Slightly Soluble
λmax
264 nm
SMILES
NC1=CC=C(S(N)(=O)=O)C=C1
InChi Code
InChI=1S/C6H8N2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H2,8,9,10)
InChi Key
FDDDEECHVMSUSB-UHFFFAOYSA-N
Shipping & Storage Information
Storage
4°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Sulfanilamide is a sulfonamide antibiotic.1 It is bacteriostatic against Streptococcus when used at a concentration of 20 μg/ml and inhibits the growth of 106 clinical isolates of Gonococcus at 0.01% v/v.1,2 Sulfanilamide reduces plasma levels of Streptococcus in infected rabbits.3 It is an inhibitor of carbonic anhydrase II (CAII) and CAIX (Kis = 294 and 300 nM, respectively, for the human enzymes).4 It is selective for CAII and CAIX over CAI and CAIV (Kis = 3000 and >10,000 nM, respectively, for the bovine and human enzymes). Sulfanilamide inhibits the growth of S. haemolyticus and E. coli when used at a concentration of 300 µM.5 Formulations containing sulfanilamide have been used in the topical treatment of vaginal fungal infections.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. White, H.J., and Parker, J.M. The bactericidal effect of sulfanilamide upon beta hemolytic streptococci in vitro. J. Bacteriol. 36(5), 481-498 (1938).

    2. Carpenter, C.M., and Wingate, H.F. The "Sulfanilamide Death Time" in vitro of 106 strains of the Gonococcus. J. Bacteriol. 41(4), 473-478 (1941).

    3. Gay, F.G., and Clark, A.R. On the mode of action of sulfanilamide in experimental streptococcus empyema. J. Exp. Med. 66(5), 535-548 (1937).

    4. Vullo, D., Franchi, M., Gallori, E., et alCarbonic anhydrase inhibitors: Inhibition of the tumor-associated isozyme IX with aromatic and heterocyclic sulfonamides. Bioorg. Med. Chem. Lett. 13(6), 1005-1009 (2003).

    5. McIlwain, H. The biochemical specificity of sulfanilamide and of other antibacterial agents. Science 95(2472), 509-511 (1942).