primaquine

Ligand id: 9952

Name: primaquine

Structure and Physico-chemical Properties

2D Structure
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 2.13
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))
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. It is effective against all exoerythrocytic forms of the malaria parasite, including the hypnozoite and is also active against the sexual blood stage (gametocytes). Primaquine is the only approved drug that is currently available for terminal prophylaxis to prevent relapse or delayed-onset clinical presentation of P. vivax and P. ovale malaria.
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).
Primaquine is one of the antimalarials listed in the WHO 20th Essential Medicines List (2017).

Potential Target/Mechanism Of Action: As the precise mechanism of action of primaquine is not yet known, we do not have a molecular target for this compound.
Database Links
CAS Registry No. 90-34-6 (source: Scifinder)
ChEBI CHEBI:8405
ChEMBL Ligand CHEMBL506
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
Search UniChem for chemical match using the InChIKey INDBQLZJXZLFIT-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone INDBQLZJXZLFIT
Wikipedia Primaquine