A sulfonamide antibiotic
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Labeled Version(s)
37200Sulfadoxin-d4
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Sulfadoxin

Item No. 21488

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-amino-N-(5,6-dimethoxy-4-pyrimidinyl)-benzenesulfonamide
CAS Number
2447-57-6
Synonyms
  • Ro 4-4393
Molecular Formula
C12H14N4O4S
Formula Weight
310.3
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
273 nm
SMILES
NC1=CC=C(S(N(C2=NC=NC(OC)=C2OC)[H])(=O)=O)C=C1
InChi Code
InChI=1S/C12H14N4O4S/c1-19-10-11(14-7-15-12(10)20-2)16-21(17,18)9-5-3-8(13)4-6-9/h3-7H,13H2,1-2H3,(H,14,15,16)
InChi Key
PJSFRIWCGOHTNF-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    Sulfadoxin is a sulfonamide antibiotic that inhibits dihydropteroate synthetase (DHPS), an enzyme involved in folic acid (Item No. 20515) synthesis.1 Sulfadoxin competes with 4-aminobenzoate (PABA), the native substrate of DHPS, and inhibits PABA incorporation into folic acid.2 Folate is essential for purine and pyrimidine synthesis, therefore, sulfadoxin has antiproliferative activity in non-resistant P. falciparum.2,3 Sulfadoxin inhibits growth of P. falciparum in vitro, but potency varies between non-resistant (IC50 = 4 ng/ml) and resistant strains (IC50 = 3,970 ng/ml).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Brooks, D.R., Wang, P., Read, M., et al. Sequence variation of the hydroxymethyldihydropterin pyrophosphokinase: dihydropteroate synthase gene in lines of the human malaria parasite, Plasmodium falciparum, with differing resistance to sulfadoxine. Eur. J. Biochem. 224(2), 397-405 (1994).

    2. Hyde, J.E. Exploring the folate pathway in Plasmodium falciparum. Acta. Trop. 94(3), 191-206 (2005).

    3. Wang, P., Read, M., Sims, P.F.G., et al. Sulfadoxine resistance in the human malaria parasite Plasmodium falciparum is determined by mutations in dihydropteroate synthetase and an additional factor associated with folate utilization. Mol. Microbiol. 23(5), 979-986 (1997).