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Oxamniquine

July 24, 2017
Common Name

Oxamniquine Description

An 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

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source MansilKegg VansilKegg OxaminiquineMeSH

Chemical Formlia

C14H21N3O3 Average Molecliar Weight

279.3348 Monoisotopic Molecliar Weight

279.158291553 IUPAC Name

(7-nitro-2-{[(propan-2-yl)amino]methyl}-1,2,3,4-tetrahydroquinolin-6-yl)methanol Traditional Name

oxamniquine CAS Registry Number

21738-42-1 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 Key

XCGYUJZMCCFSRP-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as nitroquinolines and derivatives. These are compounds containing a nitro group attached to a quinoline moiety. Kingdom

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Quinolines and derivatives Direct Parent

Nitroquinolines and derivatives Alternative Parents

  • Hydroquinolines
  • Nitroaromatic compounds
  • Secondary alkylarylamines
  • Aralkylamines
  • Benzenoids
  • Propargyl-type 1,3-dipolar organic compounds
  • Organic oxoazanium compounds
  • Dialkylamines
  • Azacyclic compounds
  • Primary alcohols
  • Organopnictogen compounds
  • Organic zwitterions
  • Organic oxides
  • Hydrocarbon derivatives
  • Aromatic alcohols

    • Substituents

  • Nitroquinoline
  • Tetrahydroquinoline
  • Nitroaromatic compound
  • Secondary aliphatic/aromatic amine
  • Aralkylamine
  • Benzenoid
  • C-nitro compound
  • Organic nitro compound
  • Secondary aliphatic amine
  • Organic oxoazanium
  • Secondary amine
  • Allyl-type 1,3-dipolar organic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Azacycle
  • Organic oxide
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic alcohol
  • Organic zwitterion
  • Hydrocarbon derivative
  • Alcohol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • C-nitro compound (CHEBI:78416 )
  • quinolines (CHEBI:78416 )
  • secondary amino compound (CHEBI:78416 )
  • aromatic primary alcohol (CHEBI:78416 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Schistosomicides

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point147 – 149 °CNot Available Boiling PointNot AvailableNot Available Water Solubility1.24e-01 g/LNot Available LogP1.5Not Available

    Predicted Properties

    Property Value Source Water Solubility0.12 mg/mLALOGPS 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 Area90.11 Å2ChemAxon Rotatable Bond Count5ChemAxon Refractivity79.87 m3·mol-1ChemAxon Polarizability30.19 Å3ChemAxon Number of Rings2ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-001i-0090000000-cbc05dcd3c76cb5e6dbcView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-00di-0090000000-13f1262c88faee196444View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-00di-0950000000-082ec38664b574d25a9cView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-00dj-0900000000-781fed8c05ecf56fc5b6View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-006t-0900000000-9e5d872a8378b48f787fView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – , positivesplash10-00dj-2910000000-90237e532f4d41c89192View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01096

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01096

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01096 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

    4451 KEGG Compound ID

    C07341 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Oxamniquine NuGOwiki Link

    HMDB15228 Metagene Link

    HMDB15228 METLIN ID

    Not Available PubChem Compound

    4612 PDB ID

    Not Available ChEBI ID

    163445

    Product: ATB-347

    References Synthesis Reference See 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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

    PMID: 10778990

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