Record Information
Version3.6
Creation Date2012-09-06 15:16:51 UTC
Update Date2013-02-09 00:33:14 UTC
HMDB IDHMDB15219
Secondary Accession NumbersNone
Metabolite Identification
Common NamePrimaquine
DescriptionAn aminoquinoline that is given by mouth to produce a radical cure and prevent relapse of vivax and ovale malarias following treatment with a blood schizontocide. It has also been used to prevent transmission of falciparum malaria by those returning to areas where there is a potential for re-introduction of malaria. Adverse effects include anemias and GI disturbances. (From Martindale, The Extra Pharmacopeia, 30th ed, p404)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC15H21N3O
Average Molecular Weight259.3467
Monoisotopic Molecular Weight259.168462309
IUPAC NameN-(5-aminopentan-2-yl)-6-methoxyquinolin-8-amine
Traditional IUPAC Nameprimaquine
CAS Registry Number90-34-6
SMILES
COC1=CC(NC(C)CCCN)=C2N=CC=CC2=C1
InChI Identifier
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 KeyINDBQLZJXZLFIT-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassQuinolines and Derivatives
Sub ClassAminoquinolines and Derivatives
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Hydroxyquinolines
  • N-substituted diamine(ChEBI)
  • aminoquinoline(ChEBI)
Substituents
  • Alkyl Aryl Ether
  • Anisole
  • Polyamine
  • Primary Aliphatic Amine (Alkylamine)
  • Pyridine
Direct ParentAminoquinolines and Derivatives
Ontology
StatusExpected and Not Quantified
Origin
  • Drug
Biofunction
  • Antimalarial Agents
  • Antimalarials
  • Antiprotozoal Agents
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.64e-02 g/LNot Available
LogP2.1Not Available
Predicted Properties
PropertyValueSource
water solubility0.056 g/LALOGPS
logP2.76ALOGPS
logP1.64ChemAxon
logS-3.7ALOGPS
pKa (strongest acidic)17.11ChemAxon
pKa (strongest basic)10.2ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count2ChemAxon
polar surface area60.17ChemAxon
rotatable bond count6ChemAxon
refractivity78.51ChemAxon
polarizability29.92ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01087
  • Not Applicable
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01087
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01087
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4739
KEGG Compound IDC07627
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPrimaquine
NuGOwiki LinkHMDB15219
Metagene LinkHMDB15219
METLIN IDNot Available
PubChem Compound4908
PDB IDNot Available
ChEBI ID8405
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mihaly GW, Ward SA, Edwards G, Nicholl DD, Orme ML, Breckenridge AM: Pharmacokinetics of primaquine in man. I. Studies of the absolute bioavailability and effects of dose size. Br J Clin Pharmacol. 1985 Jun;19(6):745-50. Pubmed: 4027117
  2. Cohen RJ, Sachs JR, Wicker DJ, Conrad ME: Methemoglobinemia provoked by malarial chemoprophylaxis in Vietnam. N Engl J Med. 1968 Nov 21;279(21):1127-31. Pubmed: 5686480
  3. Coleman MD, Coleman NA: Drug-induced methaemoglobinaemia. Treatment issues. Drug Saf. 1996 Jun;14(6):394-405. Pubmed: 8828017
  4. ALVING AS, ARNOLD J, HOCKWALD RS, CLAYMAN CB, DERN RJ, BEUTLER E, FLANAGAN CL: Potentiation of the curative action of primaquine in vivax malaria by quinine and chloroquine. J Lab Clin Med. 1955 Aug;46(2):301-6. Pubmed: 13242948
  5. Hill DR, Baird JK, Parise ME, Lewis LS, Ryan ET, Magill AJ: Primaquine: report from CDC expert meeting on malaria chemoprophylaxis I. Am J Trop Med Hyg. 2006 Sep;75(3):402-15. Pubmed: 16968913

Enzymes

Gene Name:
CYP3A4
Uniprot ID:
P08684
Gene Name:
CYP1B1
Uniprot ID:
Q16678
Gene Name:
CYP2D6
Uniprot ID:
P10635
Gene Name:
CYP1A1
Uniprot ID:
P04798
Gene Name:
CYP1A2
Uniprot ID:
P05177