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
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)
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 Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
2061 sulfadoxine
Synonyms Click here for help
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Sulfadoxine, sulforthomidine, sulformethoxin, sulphorthodimethoxine
Other databases
CAS Registry No. 2447-57-6 (source: Scifinder)
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
UniChem Compound Search for chemical match using the InChIKey PJSFRIWCGOHTNF-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey PJSFRIWCGOHTNF-UHFFFAOYSA-N