sulfadoxine   Click here for help

GtoPdb Ligand ID: 10173

Synonyms: sulphadoxine
Approved drug Antimalarial Ligand
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.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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 Click here for help
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 Click here for help
4-amino-N-(5,6-dimethoxypyrimidin-4-yl)benzenesulfonamide
International Nonproprietary Names Click here for help
INN number INN
2061 sulfadoxine
Synonyms Click here for help
sulphadoxine
Database Links Click here for help
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
Search Google for chemical match using the InChIKey PJSFRIWCGOHTNF-UHFFFAOYSA-N
Search Google for chemicals with the same backbone PJSFRIWCGOHTNF
Search PubMed clinical trials sulfadoxine
Search PubMed titles sulfadoxine
Search PubMed titles/abstracts sulfadoxine
Search UniChem for chemical match using the InChIKey PJSFRIWCGOHTNF-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone PJSFRIWCGOHTNF