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Record Information
Version3.6
Creation Date2012-09-06 15:16:51 UTC
Update Date2013-02-09 00:33:15 UTC
HMDB IDHMDB15228
Secondary Accession NumbersNone
Metabolite Identification
Common NameOxamniquine
DescriptionAn anthelmintic with schistosomicidal activity against Schistosoma mansoni, but not against other Schistosoma spp. Oxamniquine causes worms to shift from the mesenteric veins to the liver where the male worms are retained; the female worms return to the mesentery, but can no longer release eggs. (From Martidale, The Extra Pharmacopoeia, 31st ed, p121)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC14H21N3O3
Average Molecular Weight279.3348
Monoisotopic Molecular Weight279.158291553
IUPAC Name(7-nitro-2-{[(propan-2-yl)amino]methyl}-1,2,3,4-tetrahydroquinolin-6-yl)methanol
Traditional IUPAC Nameoxamniquine
CAS Registry Number21738-42-1
SMILES
CC(C)NCC1CCC2=CC(CO)=C(C=C2N1)[N+]([O-])=O
InChI Identifier
InChI=1S/C14H21N3O3/c1-9(2)15-7-12-4-3-10-5-11(8-18)14(17(19)20)6-13(10)16-12/h5-6,9,12,15-16,18H,3-4,7-8H2,1-2H3
InChI KeyXCGYUJZMCCFSRP-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassQuinolines and Derivatives
Sub ClassHydroquinolines
Other Descriptors
  • Nitrobenzenes
Substituents
  • Nitro Compound
  • Organic Oxoazanium
  • Primary Alcohol
  • Secondary Aliphatic Amine (Dialkylamine)
Direct ParentHydroquinolines
Ontology
StatusExpected and Not Quantified
Origin
  • Drug
Biofunction
  • Schistosomicides
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point147 - 149 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.24e-01 g/LNot Available
LogP1.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP1.54ALOGPS
logP1.57ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)14.55ChemAxon
pKa (Strongest Basic)9.9ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area90.11ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity79.87ChemAxon
Polarizability30.19ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01096
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01096
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01096
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4451
KEGG Compound IDC07341
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOxamniquine
NuGOwiki LinkHMDB15228
Metagene LinkHMDB15228
METLIN IDNot Available
PubChem Compound4612
PDB IDNot Available
ChEBI ID163445
References
Synthesis ReferenceSee General references, Filho et. al. for synthesis of oxamniquine methacylate.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Filho RP, de Souza Menezes CM, Pinto PL, Paula GA, Brandt CA, da Silveira MA: Design, synthesis, and in vivo evaluation of oxamniquine methacrylate and acrylamide prodrugs. Bioorg Med Chem. 2007 Feb 1;15(3):1229-36. Epub 2006 Nov 16. Pubmed: 17134907

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed: 19934256