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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2017-12-07 02:52:38 UTC
HMDB IDHMDB0015684
Secondary Accession Numbers
  • HMDB15684
Metabolite Identification
Common NameDiloxanide
DescriptionDiloxanide 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
Thumb
Synonyms
ValueSource
Diloxanide furoateHMDB
2-FuramideMeSH
FuramideMeSH
2,2-dichloro-4'-Hydroxy-N-methylacetanilide 2-furoateMeSH
Entamide furoateMeSH
Chemical FormulaC14H11Cl2NO4
Average Molecular Weight328.147
Monoisotopic Molecular Weight327.006513259
IUPAC Name4-(2,2-dichloro-N-methylacetamido)phenyl furan-2-carboxylate
Traditional Namediloxanide
CAS Registry Number3736-81-0
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 KeyBDYYDXJSHYEDGB-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassPhenol esters
Direct ParentPhenol esters
Alternative Parents
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
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.038 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity78.21 m³·mol⁻¹ChemAxon
Polarizability30.28 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9210000000-155781bb2d496f2f73d6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-9321100000-2db11dd84428f82ca90eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0329000000-1262050a3c668ecb16ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00or-0759000000-713dc68946d3510d857aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0229-0900000000-e8be416029e730eec9b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0019000000-cebc6857c99a38b12002View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00or-0479000000-1fd0103d81f6101d6ccfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-4910000000-8e2db9b32afa86e51d0aView in MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB08792 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB08792 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB08792
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID18400
KEGG Compound IDC07637
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDiloxanide_furoate
METLIN IDNot Available
PubChem Compound19529
PDB IDNot Available
ChEBI ID858744
References
Synthesis ReferenceNot 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 ]