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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL506
CHEMBL506
Compound Name PRIMAQUINE
ChEMBL Synonyms PRIMAQUINE PHOSPHATE | PRIMACHINE PHOSPHATE | PRIMAQUINE
Max Phase 4 (Approved)
Trade Names PRIMAQUINE | PRIMAQUINE PHOSPHATE
Molecular Formula C15H21N3O

Additional synonyms for CHEMBL506 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES COc1cc(NC(C)CCCN)c2ncccc2c1
Standard InChI InChI=1S/C15H21N3O/c1-11(5-3-7-16)18-14-10-13(19-2)9-12-6-4- ...
Download InChI
Standard InChI Key INDBQLZJXZLFIT-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • DrugMatrix
  • Harvard Malaria Screening
  • MMV Pathogen Box
  • Manually Added Drugs
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL506

Molecule Features

CHEMBL506 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Racemic Mixture Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Unknown Not Available PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Glucosephosphate Dehydrogenase DeficiencyD005955EFO:0007287glucosephosphate dehydrogenase deficiency1ClinicalTrials
ClinicalTrials
MalariaD008288EFO:0001068malaria4ATC
ClinicalTrials
Malaria, FalciparumD016778EFO:0007444Plasmodium falciparum malaria3ClinicalTrials
Malaria, VivaxD016780EFO:0007445Plasmodium vivax malaria3ClinicalTrials
ClinicalTrials
ObesityD009765EFO:0001073obesity1ClinicalTrials

Clinical Data

ClinicalTrials.gov PRIMAQUINE
The Cochrane Collaboration PRIMAQUINE

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
259.4 259.1685 2.78 6 60.17 BASE


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
4 2 0 4 3 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 10.38 2.74 .01 2 19 0.84

Structural Alerts

There are no structural alerts for CHEMBL506

Compound Cross References

ATC P - ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
P01 - ANTIPROTOZOALS
P01B - ANTIMALARIALS
P01BA - Aminoquinolines
P01BA03 - primaquine

ChemSpider ChemSpider:INDBQLZJXZLFIT-UHFFFAOYSA-N
DailyMed primaquine phosphate
PubChem SID: 174006623 SID: 24715072 SID: 24715073 SID: 50123426
Wikipedia Primaquine

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL506



ACToR 90-34-6
BindingDB 71542
Brenda 83785 5715
ChEBI 8405
DrugBank DB01087
DrugCentral 2266
eMolecules 1077024
EPA CompTox Dashboard DTXSID8023509
Guide to Pharmacology 9952
Human Metabolome Database HMDB0015219
IBM Patent System 507CF1735477E929E832B1C99E8BAE62
KEGG Ligand C07627
LINCS LSM-1649
Mcule MCULE-1557087031
MolPort MolPort-001-794-628
Nikkaji J4.316H
PharmGKB PA451103
PubChem 4908
PubChem: Thomson Pharma 14798934
SureChEMBL SCHEMBL22207

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/INDBQLZJXZLFIT-UHFFFAOYSA-N spacer
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