primaquine   Click here for help

GtoPdb Ligand ID: 9952

Approved drug PDB Ligand Antimalarial Ligand
primaquine is an approved drug (FDA (1952))
Compound class: Synthetic organic
Comment: Primaquine is a synthetic, 8-aminoquinoline derivative that has potent antimalarial activity.
The approved drug is a racemic mixture and we show the chemical structure without stereochemistry to represent the mixture. The non-isomeric structure is also represented in the PubChem, ChEMBL and ChEBI entries listed in the links table below, while the two enantiomers forming the racemate are represented by PubChem CID 3044368 and PubChem CID 3044369.
The marketed formulations contain primaquine phosphate (PubChem CID 6135).

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 3
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 60.17
Molecular weight 259.17
XLogP 2.09
No. Lipinski's rules broken 0
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Canonical SMILES NCCCC(Nc1cc(OC)cc2c1nccc2)C
Isomeric SMILES NCCCC(Nc1cc(OC)cc2c1nccc2)C
InChI InChI=1S/C15H21N3O/c1-11(5-3-7-16)18-14-10-13(19-2)9-12-6-4-8-17-15(12)14/h4,6,8-11,18H,3,5,7,16H2,1-2H3
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
Approved drug? Yes (FDA (1952))
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
218 primaquine
Database Links Click here for help
CAS Registry No. 90-34-6 (source: Scifinder)
DrugCentral Ligand 2266
GtoPdb PubChem SID 374883839
PubChem CID 4908
Search Google for chemical match using the InChIKey INDBQLZJXZLFIT-UHFFFAOYSA-N
Search Google for chemicals with the same backbone INDBQLZJXZLFIT
Search PubMed clinical trials primaquine
Search PubMed titles primaquine
Search PubMed titles/abstracts primaquine
UniChem Compound Search for chemical match using the InChIKey INDBQLZJXZLFIT-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey INDBQLZJXZLFIT-UHFFFAOYSA-N
Wikipedia Primaquine