pyrimethamine   

GtoPdb Ligand ID: 4800

Synonyms: Daraprim® | GNF-Pf-5586 | TCMDC-125860
pyrimethamine is an approved drug (FDA (1953))
Compound class: Synthetic organic
Comment: Pyrimethamine is an antifolate compound with broad-spectrum antiprotozoal activity. It is used in the treatment and prevention of malaria as part of a combination therapy.

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: pyrimethamine

2D Structure
Click here for structure editor
Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 77.82
Molecular weight 248.08
XLogP 2.68
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CCc1nc(N)nc(c1c1ccc(cc1)Cl)N
Isomeric SMILES CCc1nc(N)nc(c1c1ccc(cc1)Cl)N
InChI InChI=1S/C12H13ClN4/c1-2-9-10(11(14)17-12(15)16-9)7-3-5-8(13)6-4-7/h3-6H,2H2,1H3,(H4,14,15,16,17)
InChI Key WKSAUQYGYAYLPV-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
Approved drug? Yes (FDA (1953))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name
5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine
International Nonproprietary Names
INN number INN
2215 pyrimethamine
Synonyms
Daraprim® | GNF-Pf-5586 | TCMDC-125860
Database Links
CAS Registry No. 58-14-0 (source: Scifinder)
ChEBI CHEBI:8673
ChEMBL Ligand CHEMBL36
DrugBank Ligand DB00205
DrugCentral Ligand 2332
GtoPdb PubChem SID 178101502
PubChem CID 4993
RCSB PDB Ligand CP6
Search Google for chemical match using the InChIKey WKSAUQYGYAYLPV-UHFFFAOYSA-N
Search Google for chemicals with the same backbone WKSAUQYGYAYLPV
Search PubMed clinical trials pyrimethamine
Search PubMed titles pyrimethamine
Search PubMed titles/abstracts pyrimethamine
Search UniChem for chemical match using the InChIKey WKSAUQYGYAYLPV-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone WKSAUQYGYAYLPV
Wikipedia Pyrimethamine

Product suppliers

View disclaimer

Tocris
Pyrimethamine
Cat. No. 3918