primaquine

Ligand id: 9952

Name: primaquine

Structure and Physico-chemical Properties

2D Structure
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Calculated Physico-chemical Properties
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

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
Approved drug? Yes (FDA (1952))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name
N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine
International Nonproprietary Names
INN number INN
218 primaquine
Comments
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.
Database Links
CAS Registry No. 90-34-6 (source: Scifinder)
ChEBI CHEBI:8405
ChEMBL Ligand CHEMBL506
GtoPdb PubChem SID 374883839
PubChem CID 4908
RCSB PDB Ligand 1PQ
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
Search UniChem for chemical match using the InChIKey INDBQLZJXZLFIT-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone INDBQLZJXZLFIT
Wikipedia Primaquine