General
Preferred name
PRIMAQUINE
Synonyms
PRIMAQUINE PHOSPHATE ()
Primaquine bisphosphate ()
Primaquine Diphosphate ()
Primaquine Diphosphate63-45-6 ()
Primaquine (Diphosphate) ()
Primaquine (phosphate) ()
Primaquine (bisphosphate) ()
Primaquine diphosphate ()
WR 2975 ()
Camden ()
NSC-149765 ()
Malquine ()
Primaquini diphosphas ()
WR-2975 ()
NSC-27296 ()
Kanaprim ()
Neo-quipenyl ()
Primachin ()
Maliride ()
SN-13272 ()
Primaquina ()
Primaquine ()
Primaquine monophosphate ()
P&D ID
PD009815
CAS
90-34-6
63-45-6
66616-84-0
Tags
available
drug
Approved by
FDA
First approval
1952
Drug indication
Malaria
Drug Status
approved
Max Phase
4.0
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
PRICE 29
DESCRIPTION Primaquine diphosphate is a potent antimalaria agent and a potent gametocytocide in falciparum malaria. Primaquine diphosphate prevents relapse in vivax and ovale malaria[1].
DESCRIPTION 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. (GtoPdb)
DESCRIPTION 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.
DESCRIPTION Primaquine is a potent antimalaria agent and a potent gametocytocide in falciparum malaria. Primaquine prevents relapse in vivax and ovale malaria[1][2].
PRICE 29
DESCRIPTION Primaquine phosphate inhibits integrase (HIV). (Enamine Bioactive Compounds)
DESCRIPTION Primaquine is the only generally available anti-malarial that prevents relapse in vivax and ovale malaria, and the only potent gametocytocide in falciparum malaria. (BOC Sciences Bioactive Compounds)
DESCRIPTION Primaquine diphosphate is the phosphate salt form of primaquine, a synthetic, 8-aminoquinoline derivative with antimalarial properties. Although its mechanism of action is unclear, primaquine bind to and alter the properties of protozoal DNA. This agent eliminates tissue (exo-erythrocytic) malarial infection, preventing the development of the erythrocytic forms of the parasite which are responsible for relapses in Plasmodium vivax and ovale malaria. Primaquine is active against late hepatic stages (hypnozoites, schizonts). (TargetMol Bioactive Compound Library)
DESCRIPTION Primaquine is an antimalarial compound and a gametocytocide, clearing liver schizonts and dormant forms of Plasmodium vivax. (TargetMol Bioactive Compound Library)
Cell lines
15
Organisms
7
Compound Sets
27
Axon Medchem Screening Library
3177
BOC Sciences Bioactive Compounds
primaquine-bisphosphate-cas-63-45-6-74002
Cayman Chemical Bioactives
18223
ChEMBL Approved Drugs
CHEMBL43128
CHEMBL506
ChEMBL Drugs
CHEMBL43128
CHEMBL506
DrugBank
DB01087
DrugBank Approved Drugs
DB01087
DrugCentral
2266
DrugCentral Approved Drugs
2266
DrugMAP
DMWQ16I
DrugMAP Approved Drugs
DMWQ16I
DrugMatrix
Enamine Bioactive Compounds
EBC-06855
Enamine BioReference Compounds
Guide to Pharmacology
9952
LSP-MoA library (Laboratory of Systems Pharmacology)
CHEMBL506
MedChem Express Bioactive Compound Library
HY-12651
HY-12651A
NCATS Inxight Approved Drugs
MVR3634GX1
NIH Clinical Collections (NCC)
NIH Mechanistic Set
NPC Screening Collection
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
primaquine-diphosphate
TargetMol Bioactive Compound Library
T0850
T60411
The Pathogen Box
The Spectrum Collection
External IDs
68
Properties
(calculated by RDKit )
Molecular Weight
259.17
Hydrogen Bond Acceptors
4
Hydrogen Bond Donors
2
Rotatable Bonds
6
Ring Count
2
Aromatic Ring Count
2
cLogP
2.78
TPSA
60.17
Fraction CSP3
0.4
Chiral centers
1.0
Largest ring
6.0
QED
0.84
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Disease
REFERENCE COMPOUNDS
Target
P. falciparum
antibiotic
Parasite
Antimalarial drug
MOA
Antibiotic
Pathway
Microbiology/virology
Anti-infection
Therapeutic Class
Antimalarials
Source data