Human Metabolome Database Version 3.5

Showing metabocard for Diloxanide (HMDB15684)

Record Information
Version 3.5
Creation Date 2012-09-06 09:16:52 -0600
Update Date 2013-02-08 17:34:15 -0700
HMDB ID HMDB15684
Secondary Accession Numbers None
Metabolite Identification
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 Thumb
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Synonyms
  1. Diloxanide furoate
Chemical Formula C14H11Cl2NO4
Average Molecular Weight 328.147
Monoisotopic Molecular Weight 327.006513259
IUPAC Name 4-(2,2-dichloro-N-methylacetamido)phenyl furan-2-carboxylate
Traditional IUPAC Name diloxanide furoate
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
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Phenylacetic Acid Derivatives
Sub Class N/A
Other Descriptors
  • Anilides
  • Aromatic Heteropolycyclic Compounds
Substituents
  • Alkyl Chloride
  • Carboxamide Group
  • Carboxylic Acid Ester
  • Furan
  • Furoate
  • Organochloride
  • Tertiary Carboxylic Acid Amide
Direct Parent Phenylacetic Acid Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Drug
Biofunction Not Available
Application
  • Pharmaceutical
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.038 g/L ALOGPS
LogP 3.33 ALOGPS
LogP 3.08 ChemAxon
LogS -3.93 ALOGPS
pKa (strongest acidic) 13.09 ChemAxon
pKa (strongest basic) -4.7 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 59.75 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 78.21 ChemAxon
Polarizability 30.28 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular 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
Blood Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB08792
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB08792
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB08792 Link_out
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 Link_out
KEGG Compound ID C07637 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Diloxanide_furoate Link_out
NuGOwiki Link HMDB15684 Link_out
Metagene Link HMDB15684 Link_out
METLIN ID Not Available
PubChem Compound 19529 Link_out
PDB ID Not Available
ChEBI ID 858744 Link_out
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 Link_out