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Diloxanide

July 24, 2017
Common Name

Diloxanide Description

Diloxanide furoate is an anti-protozoal drug used in the treatment of Entamoeba histolytica and some other protozoal infections. Although it is not currently approved for use in the United States, it was approved by a CDC study in the treatment of 4,371 cases of Entamoeba histolytica from 1977 to 1990. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source Diloxanide furoateHMDB 2-FuramideMeSH FuramideMeSH 2,2-dichloro-4'-Hydroxy-N-methylacetanilide 2-furoateMeSH Entamide furoateMeSH

Chemical Formlia

C14H11Cl2NO4 Average Molecliar Weight

328.147 Monoisotopic Molecliar Weight

327.006513259 IUPAC Name

4-(2,2-dichloro-N-methylacetamido)phenyl furan-2-carboxylate Traditional Name

diloxanide CAS Registry Number

3736-81-0 SMILES

CN(C(=O)C(Cl)Cl)C1=CC=C(OC(=O)C2=CC=CO2)C=C1

InChI Identifier

InChI=1S/C14H11Cl2NO4/c1-17(13(18)12(15)16)9-4-6-10(7-5-9)21-14(19)11-3-2-8-20-11/h2-8,12H,1H3

InChI Key

BDYYDXJSHYEDGB-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group. Kingdom

Chemical entities Super Class

Organic compounds Class

Benzenoids Sub Class

Phenol esters Direct Parent

Phenol esters Alternative Parents

  • Furoic acid esters
  • Anilides
  • Phenoxy compounds
  • Tertiary carboxylic acid amides
  • Heteroaromatic compounds
  • Carboxylic acid esters
  • Oxacyclic compounds
  • Monocarboxylic acids and derivatives
  • Organopnictogen compounds
  • Organonitrogen compounds
  • Organochlorides
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds
  • Alkyl chlorides

    • Substituents

  • Phenol ester
  • Furoic acid ester
  • Anilide
  • Furoic acid or derivatives
  • Phenoxy compound
  • Monocyclic benzene moiety
  • Furan
  • Tertiary carboxylic acid amide
  • Heteroaromatic compound
  • Carboxamide group
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Alkyl halide
  • Organopnictogen compound
  • Alkyl chloride
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound

    • Molecliar Framework

    Aromatic heteromonocyclic compounds External Descriptors

  • phenols (CHEBI:4601 )
  • benzoate ester (CHEBI:4601 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

    Not Available Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane (predicted from logP)

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.038 mg/mLALOGPS logP3.33ALOGPS logP3.08ChemAxon logS-3.9ALOGPS pKa (Strongest Acidic)13.09ChemAxon pKa (Strongest Basic)-4.7ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count2ChemAxon Hydrogen Donor Count0ChemAxon Polar Surface Area59.75 Å2ChemAxon Rotatable Bond Count5ChemAxon Refractivity78.21 m3·mol-1ChemAxon Polarizability30.28 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 – , positivesplash10-0002-9321100000-2db11dd84428f82ca90eView 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

  • Membrane (predicted from logP)

    • 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 DB08792

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB08792

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB08792 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

    18400 KEGG Compound ID

    C07637 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Diloxanide_furoate NuGOwiki Link

    HMDB15684 Metagene Link

    HMDB15684 METLIN ID

    Not Available PubChem Compound

    19529 PDB ID

    Not Available ChEBI ID

    858744

    Product: MI-774

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. McAuley JB, Herwaldt BL, Stokes SL, Becher JA, Roberts JM, Michelson MK, Juranek DD: Diloxanide furoate for treating asymptomatic Entamoeba histolytica cyst passers: 14 years experience in the United States. Clin Infect Dis. 1992 Sep;15(3):464-8. [PubMed:1520794 ]

    PMID: 16797584

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