sulfadoxine   

GtoPdb Ligand ID: 10173

Synonyms: sulphadoxine
sulfadoxine is an approved drug (FDA (1981) in combination with pyrimethamine)
Compound class: Synthetic organic
Comment: Sulfadoxine is a sulfonamide containing compound with antimalarial activity. It is used in the treatment of malaria as a combination therapy.

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 124.81
Molecular weight 310.07
XLogP 0.62
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES COc1c(OC)ncnc1NS(=O)(=O)c1ccc(cc1)N
Isomeric SMILES COc1c(OC)ncnc1NS(=O)(=O)c1ccc(cc1)N
InChI 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
Whole organism assay data
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MOA/likely target Sp. Assay description Type Action Value Parameter Concentration range (M) Reference
Plasmodium falciparum hydroxymethyldihydropterin pyrophosphokinase-dihydropteroate synthase PfHB3 Parasite growth inhibition assay - - 8.4 pIC50 - 1
pIC50 8.4 (IC50 4x10-9 M) [3H]-hypoxanthine incorporation [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Plasmodium falciparum hydroxymethyldihydropterin pyrophosphokinase-dihydropteroate synthase Pf3D7 Parasite growth inhibition assay - - 7.1 pIC50 - 1
pIC50 7.1 (IC50 7.3x10-8 M) [3H]-hypoxanthine incorporation [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Plasmodium falciparum hydroxymethyldihydropterin pyrophosphokinase-dihydropteroate synthase PfK1 Parasite growth inhibition assay - - 6.7 pIC50 - 1
pIC50 6.7 (IC50 2.23x10-7 M) [3H]-hypoxanthine incorporation [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Plasmodium falciparum hydroxymethyldihydropterin pyrophosphokinase-dihydropteroate synthase PfDd2 Parasite growth inhibition assay - - 5.4 pIC50 - 1
pIC50 5.4 (IC50 3.97x10-6 M) [3H]-hypoxanthine incorporation [1]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)