pyrimethamine   Click here for help

GtoPdb Ligand ID: 4800

Synonyms: Daraprim® | GNF-Pf-5586 | TCMDC-125860
Approved drug PDB Ligand Antimalarial Ligand
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.
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2D Structure
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Physico-chemical Properties
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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
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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 Click here for help
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
Approved drug? Yes (FDA (1953))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
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IUPAC Name Click here for help
5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine
International Nonproprietary Names Click here for help
INN number INN
2215 pyrimethamine
Synonyms Click here for help
Daraprim® | GNF-Pf-5586 | TCMDC-125860
Database Links Click here for help
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
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UniChem Compound Search for chemical match using the InChIKey WKSAUQYGYAYLPV-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey WKSAUQYGYAYLPV-UHFFFAOYSA-N
Wikipedia Pyrimethamine

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Tocris
Pyrimethamine (links to external site)
Cat. No. 3918