Human Metabolome Database Version 3.5

Showing metabocard for Primaquine (HMDB15219)

Record Information
Version 3.5
Creation Date 2012-09-06 09:16:51 -0600
Update Date 2013-02-08 17:33:14 -0700
HMDB ID HMDB15219
Secondary Accession Numbers None
Metabolite Identification
Common Name Primaquine
Description An 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Chemical Formula C15H21N3O
Average Molecular Weight 259.3467
Monoisotopic Molecular Weight 259.168462309
IUPAC Name N-(5-aminopentan-2-yl)-6-methoxyquinolin-8-amine
Traditional IUPAC Name primaquine
CAS Registry Number 90-34-6
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 Key INDBQLZJXZLFIT-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Quinolines and Derivatives
Sub Class Aminoquinolines 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 Parent Aminoquinolines and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Drug
Biofunction
  • Antimalarial Agents
  • Antimalarials
  • Antiprotozoal Agents
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point < 25 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 5.64e-02 g/L Not Available
LogP 2.1 Not Available
Predicted Properties
Property Value Source
Water Solubility 0.056 g/L ALOGPS
LogP 2.76 ALOGPS
LogP 1.64 ChemAxon
LogS -3.66 ALOGPS
pKa (strongest acidic) 17.11 ChemAxon
pKa (strongest basic) 10.2 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 60.17 A2 ChemAxon
Rotatable Bond Count 6 ChemAxon
Refractivity 78.51 ChemAxon
Polarizability 29.92 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB01087
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB01087
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB01087 Link_out
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID Not Available
KNApSAcK ID Not Available
Chemspider ID 4739 Link_out
KEGG Compound ID C07627 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Primaquine Link_out
NuGOwiki Link HMDB15219 Link_out
Metagene Link HMDB15219 Link_out
METLIN ID Not Available
PubChem Compound 4908 Link_out
PDB ID Not Available
ChEBI ID 8405 Link_out
References
Synthesis Reference Not 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 Link_out
  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 Link_out
  3. Coleman MD, Coleman NA: Drug-induced methaemoglobinaemia. Treatment issues. Drug Saf. 1996 Jun;14(6):394-405. Pubmed: 8828017 Link_out
  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 Link_out
  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 Link_out

Enzymes
Name: Ribosyldihydronicotinamide dehydrogenase [quinone]
Reactions: Not Available
Gene Name: NQO2
Uniprot ID: P16083 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A4
Reactions: Not Available
Gene Name: CYP3A4
Uniprot ID: P08684 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 1B1
Reactions: Not Available
Gene Name: CYP1B1
Uniprot ID: Q16678 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2D6
Reactions: Not Available
Gene Name: CYP2D6
Uniprot ID: P10635 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 1A1
Reactions: Not Available
Gene Name: CYP1A1
Uniprot ID: P04798 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 1A2
Reactions: Not Available
Gene Name: CYP1A2
Uniprot ID: P05177 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA