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Record Information
Version3.6
Creation Date2012-09-06 15:16:52 UTC
Update Date2013-02-09 00:34:15 UTC
HMDB IDHMDB15684
Secondary Accession NumbersNone
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
  1. Diloxanide furoate
Chemical FormulaC14H11Cl2NO4
Average Molecular Weight328.147
Monoisotopic Molecular Weight327.006513259
IUPAC Name4-(2,2-dichloro-N-methylacetamido)phenyl furan-2-carboxylate
Traditional Namediloxanide furoate
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
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassPhenylacetic Acid Derivatives
Sub ClassN/A
Other Descriptors
  • Anilides
  • Aromatic Heteropolycyclic Compounds
Substituents
  • Alkyl Chloride
  • Carboxamide Group
  • Carboxylic Acid Ester
  • Furan
  • Furoate
  • Organochloride
  • Tertiary Carboxylic Acid Amide
Direct ParentPhenylacetic Acid Derivatives
Ontology
StatusExpected and Not Quantified
Origin
  • Drug
BiofunctionNot Available
Application
  • Pharmaceutical
Cellular locations
  • Membrane (predicted from logP)
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 Solubility0.038ALOGPS
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
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB08792
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB08792
  • Not Applicable
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
NuGOwiki LinkHMDB15684
Metagene LinkHMDB15684
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