primaquine   

GtoPdb Ligand ID: 9952

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.
2D Structure
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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
SMILES / InChI / InChIKey
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
InChI Key INDBQLZJXZLFIT-UHFFFAOYSA-N
Guide to Malaria Pharmacology Comments
Primaquine is effective against all exoerythrocytic forms of the malaria parasite, including the hypnozoite and is also active against the sexual blood stage (gametocytes). Primaquine was, until the approval of tafenoquine in 2018, the only licensed drug available for terminal prophylaxis to prevent relapse or delayed-onset clinical presentation of P. vivax and P. ovale malaria.
Primaquine is on the World Health Organisation's List of Essential Medicines. Click here to access the pdf version of the WHO's 21st Essential Medicines list (2019).

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.