Human Metabolome Database Version 3.5

Showing metabocard for Amodiaquine (HMDB14751)

Record Information
Version 3.5
Creation Date 2012-09-06 09:16:50 -0600
Update Date 2013-02-08 17:32:14 -0700
HMDB ID HMDB14751
Secondary Accession Numbers None
Metabolite Identification
Common Name Amodiaquine
Description Amodiaquine 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Amodiaquin
  2. Amodiaquine USP24
  3. Amodiaquine, ring-closed
Chemical Formula C20H22ClN3O
Average Molecular Weight 355.861
Monoisotopic Molecular Weight 355.145140048
IUPAC Name 4-[(7-chloroquinolin-4-yl)amino]-2-[(diethylamino)methyl]phenol
Traditional IUPAC Name amodiaquine
CAS Registry Number 86-42-0
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 Key OVCDSSHSILBFBN-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
  • 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 Parent Aminoquinolines and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Drug
Biofunction
  • Amebicides
  • Antimalarials
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 208 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 8.80e-03 g/L Not Available
LogP 3.7 Not Available
Predicted Properties
Property Value Source
Water Solubility 0.0088 g/L ALOGPS
LogP 4.83 ALOGPS
LogP 3.76 ChemAxon
LogS -4.61 ALOGPS
pKa (strongest acidic) 9.12 ChemAxon
pKa (strongest basic) 10.23 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 48.39 A2 ChemAxon
Rotatable Bond Count 6 ChemAxon
Refractivity 103.29 ChemAxon
Polarizability 38.89 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 DB00613
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB00613
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB00613 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 2080 Link_out
KEGG Compound ID C07626 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Amodiaquine Link_out
NuGOwiki Link HMDB14751 Link_out
Metagene Link HMDB14751 Link_out
METLIN ID Not Available
PubChem Compound 2165 Link_out
PDB ID CQA Link_out
ChEBI ID 2674 Link_out
References
Synthesis Reference Not 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 Link_out
  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 Link_out

Enzymes
Name: Histamine N-methyltransferase
Reactions: Not Available
Gene Name: HNMT
Uniprot ID: P50135 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C9
Reactions: Not Available
Gene Name: CYP2C9
Uniprot ID: P11712 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 2C8
Reactions: Not Available
Gene Name: CYP2C8
Uniprot ID: P10632 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA