An internal standard for the quantification of sulfamethoxazole-d4
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Unlabeled Version(s)
23613Sulfamethoxazole
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Sulfamethoxazole-d4

Item No. 28618

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-amino-N-(5-methyl-3-isoxazolyl)-benzene-2,3,5,6-d4-sulfonamide
CAS Number
1020719-86-1
Molecular Formula
C10H7D4N3O3S
Formula Weight
257.3
Purity
≥99% deuterated forms (d1-d4); ≤1% d0
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: slightly solubleMethanol: slightly soluble
SMILES
NC1=C([2H])C([2H])=C(S(NC2=NOC(C)=C2)(=O)=O)C([2H])=C1[2H]
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)/i2D,3D,4D,5D
InChi Key
JLKIGFTWXXRPMT-QFFDRWTDSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Sulfamethoxazole-d4 is intended for use as an internal standard for the quantification of sulfamethoxazole (Item No. 23613) by GC- or LC-MS. 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 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).