General
Preferred name
PRIMAQUINE
Synonyms
PRIMAQUINE PHOSPHATE ()
Primaquine bisphosphate ()
Primaquine Diphosphate ()
Primaquine (Diphosphate) ()
Primaquine Diphosphate63-45-6 ()
Primaquine (phosphate) ()
Primaquine (bisphosphate) ()
Primaquine diphosphate ()
NSC-149765 ()
Malquine ()
Primachine phosphate ()
Primaquine ()
Primaquini diphosphas ()
WR 2975 ()
SN-13272 ()
Kanaprim ()
NSC-27296 ()
Neo-quipenyl ()
Primachin ()
Maliride ()
WR-2975 ()
P&D ID
PD009815
CAS
90-34-6
63-45-6
Tags
natural product
drug
available
Approved by
FDA
First approval
1952
Drug Status
approved
Drug indication
Antimalarial
Malaria
Max Phase
Phase 4
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
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)
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.
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 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)
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Cell lines
13
Organisms
11
Compound Sets
26
Axon Medchem Screening Library
BOC Sciences Bioactive Compounds
Cayman Chemical Bioactives
ChEMBL Approved Drugs
ChEMBL Drugs
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
DrugMAP
DrugMAP Approved Drugs
DrugMatrix
Enamine BioReference Compounds
Guide to Pharmacology
LSP-MoA library (Laboratory of Systems Pharmacology)
NCATS Inxight Approved Drugs
NIH Clinical Collections (NCC)
NIH Mechanistic Set
NPC Screening Collection
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
TargetMol Bioactive Compound Library
The Pathogen Box
The Spectrum Collection
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
65
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
Pathway
Microbiology&virology
Anti-infection
Target
antibiotic
Antimalarial drug
Parasite
MOA
Antibiotic
Therapeutic Class
Antimalarials
Source data
