A sulfonamide antibacterial
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Labeled Version(s)
36575Sulfamethazine-d4
Metabolite(s)
42996N-acetyl Sulfamethazine
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Sulfamethazine

Item No. 20976

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-amino-N-(4,6-dimethyl-2-pyrimidinyl)-benzenesulfonamide
CAS Number
57-68-1
Synonyms
  • NSC 67457
  • NSC 683529
  • Sulfadimethyldiazine
  • Sulfadimidine
Molecular Formula
C12H14N4O2S
Formula Weight
278.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMSO: 50 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/mlEthanol: 0.3 mg/ml
λmax
211, 269 nm
SMILES
NC1=CC=C(S(NC2=NC(C)=CC(C)=N2)(=O)=O)C=C1
InChi Code
InChI=1S/C12H14N4O2S/c1-8-7-9(2)15-12(14-8)16-19(17,18)11-5-3-10(13)4-6-11/h3-7H,13H2,1-2H3,(H,14,15,16)
InChi Key
ASWVTGNCAZCNNR-UHFFFAOYSA-N
Shipping & Storage Information
Storage
Room temperature
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    25 g

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    50 g

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    100 g

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    250 g

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    Cayman Chemical
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    Product Description

    Sulfamethazine is a sulfonamide antibiotic.1,2 It inhibits dihydropteroate synthase (DHPS; IC50 = 5.7 µM for the T. gondii enzyme). Sulfamethazine is active against A. pleuropneumoniae (MIC = 32 µg/ml) and enhances the antibacterial activity of trimethoprim (Item No. 16473) against E. coli.3,4 It has been detected in environmental water samples.5,6 Formulations containing sulfamethazine have been used in the treatment of bacterial infections in livestock.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Allegra, C.J., Boarman, D., Kovacs, J.A., et al. Interaction of sulfonamide and sulfone compounds with Toxoplasma gondii dihydropteroate synthase. J. Clin. Invest. 85(2), 371-379 (1990).

    2. Salmon, S.A., Watts, J.L., Case, C.A., et al. Comparison of MICs of ceftiofur and other antimicrobial agents against bacterial pathogens of swine from the United States, Canada, and Denmark. J. Clin. Microbiol. 33(9), 2435-2444 (1995).

    3. Mengelers, M.J., Hougee, P.E., Janssen, L.H., et al. Structure-activity relationships between antibacterial activities and physicochemical properties of sulfonamides. J. Vet. Pharmacol. Ther. 20(4), 276-283 (1997).

    4. Peng, F.-J., Ying, G.-G., Liu, Y.-S., et al. Joint antibacterial activity of soil-adsorbed antibiotics trimethoprim and sulfamethazine. Sci. Total Environ. 506-507, 58-65 (2015).

    5. Washington, M.T., Moorman, T.B., Soupir, M.L., et al. Monitoring tylosin and sulfamethazine in a tile-drained agricultural watershed using polar organic chemical integrative sampler (POCIS). Sci. Total. Environ. 612, 358-367 (2017).

    6. López-Serna, R., Petrović, M., and Barceló, D. Direct analysis of pharmaceuticals, their metabolites and transformation products in environmental waters using on-line TurboFlow™ chromatography-liquid chromatography-tandem mass spectrometry. J. Chomatogr. A. 1252, 115-129 (2012).