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
Classification
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
Approved drug? Yes (FDA (1981) in combination with pyrimethamine)
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name
4-amino-N-(5,6-dimethoxypyrimidin-4-yl)benzenesulfonamide
International Nonproprietary Names
INN number INN
2061 sulfadoxine
Synonyms
sulphadoxine
Database Links
CAS Registry No. 2447-57-6 (source: Scifinder)
ChEBI CHEBI:9329
ChEMBL Ligand CHEMBL1539
DrugBank Ligand DB01299
DrugCentral Ligand 2503
GtoPdb PubChem SID 381118883
PubChem CID 17134
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Search PubMed clinical trials sulfadoxine
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Search UniChem for chemical match using the InChIKey PJSFRIWCGOHTNF-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone PJSFRIWCGOHTNF