Record Information
Version3.6
Creation Date2012-09-06 15:16:50 UTC
Update Date2013-02-09 00:32:14 UTC
HMDB IDHMDB14751
Secondary Accession NumbersNone
Metabolite Identification
Common NameAmodiaquine
DescriptionAmodiaquine is only found in individuals that have used or taken this drug. It is a 4-aminoquinoquinoline compound with anti-inflammatory properties. [PubChem]The mechanism of plasmodicidal action of amodiaquine is not completely certain. Like other quinoline derivatives, it is thought to inhibit heme polymerase activity. This results in accumulation of free heme, which is toxic to the parasites. The drug binds the free heme preventing the parasite from converting it to a form less toxic. This drug-heme complex is toxic and disrupts membrane function.
Structure
Thumb
Synonyms
  1. Amodiaquin
  2. Amodiaquine USP24
  3. Amodiaquine, ring-closed
Chemical FormulaC20H22ClN3O
Average Molecular Weight355.861
Monoisotopic Molecular Weight355.145140048
IUPAC Name4-[(7-chloroquinolin-4-yl)amino]-2-[(diethylamino)methyl]phenol
Traditional IUPAC Nameamodiaquine
CAS Registry Number86-42-0
SMILES
CCN(CC)CC1=C(O)C=CC(NC2=C3C=CC(Cl)=CC3=NC=C2)=C1
InChI Identifier
InChI=1S/C20H22ClN3O/c1-3-24(4-2)13-14-11-16(6-8-20(14)25)23-18-9-10-22-19-12-15(21)5-7-17(18)19/h5-12,25H,3-4,13H2,1-2H3,(H,22,23)
InChI KeyOVCDSSHSILBFBN-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassQuinolines and Derivatives
Sub ClassAminoquinolines and Derivatives
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • a small molecule(Cyc)
  • phenols(ChEBI)
  • quinolines(ChEBI)
Substituents
  • Aminophenol Derivative
  • Aminopyridine
  • Aryl Chloride
  • Chlorobenzene
  • Organochloride
  • Phenol
  • Phenol Derivative
  • Phenylmethylamine
  • Polyamine
  • Pyridine
  • Tertiary Aliphatic Amine (Trialkylamine)
Direct ParentAminoquinolines and Derivatives
Ontology
StatusExpected and Not Quantified
Origin
  • Drug
Biofunction
  • Amebicides
  • Antimalarials
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point208 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility8.80e-03 g/LNot Available
LogP3.7Not Available
Predicted Properties
PropertyValueSource
water solubility0.0088 g/LALOGPS
logP4.83ALOGPS
logP3.76ChemAxon
logS-4.6ALOGPS
pKa (strongest acidic)9.12ChemAxon
pKa (strongest basic)10.23ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count2ChemAxon
polar surface area48.39ChemAxon
rotatable bond count6ChemAxon
refractivity103.29ChemAxon
polarizability38.89ChemAxon
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 DB00613
  • Not Applicable
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00613
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00613
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2080
KEGG Compound IDC07626
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAmodiaquine
NuGOwiki LinkHMDB14751
Metagene LinkHMDB14751
METLIN IDNot Available
PubChem Compound2165
PDB IDCQA
ChEBI ID2674
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Harrison AC, Kitteringham NR, Clarke JB, Park BK: The mechanism of bioactivation and antigen formation of amodiaquine in the rat. Biochem Pharmacol. 1992 Apr 1;43(7):1421-30. Pubmed: 1567466
  2. Jewell H, Maggs JL, Harrison AC, O'Neill PM, Ruscoe JE, Park BK: Role of hepatic metabolism in the bioactivation and detoxication of amodiaquine. Xenobiotica. 1995 Feb;25(2):199-217. Pubmed: 7618347

Enzymes

Gene Name:
HNMT
Uniprot ID:
P50135
Gene Name:
CYP2C9
Uniprot ID:
P11712
Gene Name:
CYP1B1
Uniprot ID:
Q16678
Gene Name:
CYP2D6
Uniprot ID:
P10635
Gene Name:
CYP1A1
Uniprot ID:
P04798
Gene Name:
CYP2C8
Uniprot ID:
P10632