A sulfonamide antibiotic
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Labeled Version(s)
28618Sulfamethoxazole-d4
Metabolite(s)
17247N-acetyl Sulfamethoxazole
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Sulfamethoxazole

Item No. 23613

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-amino-N-(5-methyl-3-isoxazolyl)-benzenesulfonamide
CAS Number
723-46-6
Synonyms
  • NSC 147832
  • Ro 4-2130
Molecular Formula
C10H11N3O3S
Formula Weight
253.3
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) (1:2): 0.5 mg/mlEthanol: 0.25 mg/ml
λmax
271 nm
SMILES
NC1=CC=C(S(NC2=NOC(C)=C2)(=O)=O)C=C1
InChi Code
InChI=1S/C10H11N3O3S/c1-7-6-10(12-16-7)13-17(14,15)9-4-2-8(11)3-5-9/h2-6H,11H2,1H3,(H,12,13)
InChi Key
JLKIGFTWXXRPMT-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Sulfamethoxazole is a sulfonamide antibiotic.1 It inhibits growth of E. coli (MIC = 10 μg/ml) and clinical isolates of methicillin-resistant S. aureus (MRSA; MICs = 25-50 μg/ml).2,3 Sulfamethoxazole, in combination with trimethoprim (Item No. 16473) at a ratio of 20:1, inhibits growth of MRSA in vivo in mice (MIC = 0.8 μg/ml; ED50s = 6.4 and 9.6 mg/kg for two MRSA strains).3 In a mouse model of urinary tract infection with E. coli, a combination of sulfamethoxazole and trimethoprim decreases recurrent infection when administered for 10 days.4 Sulfamethoxazole acts by inhibiting dihydropteroate synthase (DHPS), which converts a pteridine and 4-aminobenzoic acid (PABA; Item No. 18659) to dihydropteroate, an intermediate in folate biosynthesis. It inhibits recombinant P. carinii DHPS (IC50 = 23 nM; Ki = 7.5 nM) and folate biosynthesis in situ by 48.6%. Formulations containing sulfamethoxazole and trimethoprim have been used to treat bronchitis, prostatitis, and urinary tract infections among other infectious conditions.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hong, Y.-L., Hossler, P.A., Calhoun, D.H., et al. Inhibition of recombinant Pneumocystis carinii dihydropteroate synthetase by sulfa drugs. Antimicrob. Agents Chemother. 39(8), 1756-1763 (1995).

    2. Greenwood, D., and O'Grady, F. Activity and interaction of trimethoprim and sulphamethoxazole against Escherichia coli. J. Clin. Pathol. 29(2), 162-166 (1976).

    3. Elwell, L.P., Wilson, H.R., Knick, V.B., et al. In vitro and in vivo efficacy of the combination trimethoprim-sulfamethoxazole against clinical isolates of methicillin-resistant Staphylococcus aureus. Antimicrob. Agents Chemother. 29(6), 1092-1094 (1986).

    4. Schilling, J.D., Lorenz, R.G., and Hultgren, S.J. Effect of trimethoprim-sulfamethoxazole on recurrent bacteriuria and bacterial persistence in mice infected with uropathogenic Escherichia coli. Infect. Immun. 70(12), 7042-7049 (2002).