Structure via PubChem · Public domain (PubChem)
sulfadoxine
Sign in to saveAlso known as Sulforthamidine, Fanzil, Sulphormethoxine, Fanasil, Ro-44393, Sulfadoxina, Sulphadoxine, 4-Sulfanilamido-5,6-dimethoxypyrimidine
Sulfadoxine (also spelled sulphadoxine) is an ultra-long-lasting sulfonamide used in combination with pyrimethamine to treat malaria.
Chemical data
- Formula
- C12H14N4O4S
- Molecular weight
- 310.33 g/mol
- IUPAC name
- 4-amino-N-(5,6-dimethoxypyrimidin-4-yl)benzenesulfonamide
- SMILES
- COC1=C(N=CN=C1OC)NS(=O)(=O)C2=CC=C(C=C2)N
- InChIKey
- PJSFRIWCGOHTNF-UHFFFAOYSA-N
- XLogP
- 0.7
- Polar surface area
- 125 Ų
- H-bond donors
- 2
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1981
- Admin. routes
- oral
- Indications
- malaria, pregnancy, anemia (phenotype), Plasmodium falciparum malaria
via ChEMBL · EBI
Research
4,096 papers- Sulfadoxine derivatization through multicomponent reactions to obtain new antiplasmodial compounds.Bioorganic & medicinal chemistry · 2025
- Pharmacokinetics of Sulfadoxine and Pyrimethamine for Intermittent Preventive Treatment of Malaria During Pregnancy and After Delivery.CPT: pharmacometrics & systems pharmacology · 2017
- Predicting the effect of sulfadoxine-pyrimethamine uptake by pregnant women on birth weight using a generalized ordered partial proportional odds model.BMC pregnancy and childbirth · 2022
- Cotrimoxazole versus sulfadoxine-pyrimethamine for intermittent preventive treatment of malaria in HIV-infected pregnant women in Bangui, Central African Republic: A pragmatic randomised controlled trial.Tropical medicine & international health : TM & IH · 2021
- High-performance liquid chromatographic assay for the determination of sulfadoxine and N-acetyl sulfadoxine in plasma from patients infected with sensitive and resistant Plasmodium falciparum malaria.Journal of chromatography. B, Analytical technologies in the biomedical and life sciences · 2007
via PubMed
Wikidata facts
- Subclass of
- sulfonamide
- Mass
- 310.073576
- Has use
- medication
Show 5 more facts
- chemical formula
- C₁₂H₁₄N₄O₄S
- canonical SMILES
- COC1=C(N=CN=C1OC)NS(=O)(=O)C2=CC=C(C=C2)N
- World Health Organisation international non-proprietary name
- sulfadoxine
- subject has role
- bactericide
- Commons category
- Sulfadoxine
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Mechanism of action
- See also
- References
Sulfadoxine (also spelled sulphadoxine) is an ultra-long-lasting sulfonamide used in combination with pyrimethamine to treat malaria.
It is also used to prevent malaria but due to high levels of sulphadoxine-pyrimethamine resistance, this use has become less common.
Excerpted from Wikipedia’s “sulfadoxine” article, available under the CC BY-SA 4.0 licence.