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.
In the Vinony graph
Vinony's link graph records 187 inbound references to sulfadoxine, and connects out to sulfamethazine, antibiotic and fidaxomicin.
It is catalogued under topics including 4-Aminophenyl compounds, Antimalarial agents and Dihydropteroate synthetase inhibitors.
Vinony links it to 20 Wikipedia language editions.
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.