Diloxanide furoate (CHEM020213)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:55:23 UTC
Update Date2016-11-09 01:16:09 UTC
Accession NumberCHEM020213
Identification
Common NameDiloxanide furoate
ClassSmall Molecule
DescriptionA carboxylic ester resulting from the formal condensation of the carboxy group of furan-2-carboxylic acid with the hydroxy group of 2,2-dichloro-N-(4-hydroxyphenyl)-N-methylacetamide. It is a drug used for the treatment of asymptomatic amebiasis.
Contaminant Sources
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
8073 CBChEBI
AmebiazolChEBI
CB 8073ChEBI
DichlofurazolChEBI
DiclofurazolChEBI
Diloxanid furoateChEBI
Entamide furoateChEBI
FuramideChEBI
FurentominChEBI
HistomibalChEBI
MiforonChEBI
Diloxanid furoic acidGenerator
Entamide furoic acidGenerator
Diloxanide furoateHMDB
2-FuramideHMDB
2,2-Dichloro-4'-hydroxy-N-methylacetanilide 2-furoateHMDB
Diloxanide furoic acidHMDB
4-(2,2-Dichloro-N-methylacetamido)phenyl furan-2-carboxylic acidHMDB
DiloxanideMeSH
Chemical FormulaC14H11Cl2NO4
Average Molecular Mass328.147 g/mol
Monoisotopic Mass327.007 g/mol
CAS Registry Number3736-81-0
IUPAC Name4-(2,2-dichloro-N-methylacetamido)phenyl furan-2-carboxylate
Traditional Namediloxanide
SMILESCN(C(=O)C(Cl)Cl)C1=CC=C(OC(=O)C2=CC=CO2)C=C1
InChI IdentifierInChI=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
Description belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol esters
Sub ClassNot Available
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9210000000-155781bb2d496f2f73d6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-9321100000-2db11dd84428f82ca90eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0329000000-1262050a3c668ecb16ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00or-0759000000-713dc68946d3510d857aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0229-0900000000-e8be416029e730eec9b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0019000000-cebc6857c99a38b12002Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00or-0479000000-1fd0103d81f6101d6ccfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-4910000000-8e2db9b32afa86e51d0aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-b367b5d264a721a31829Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1029000000-970964c4b48692161e11Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006t-6921000000-06fe5bc95cea9426f994Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-341d0e7a1b163c73a23aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ea-5496000000-ab18fdf2aed6acb29d76Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00e9-5930000000-9c89cb45f3d811d650fcSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDBSALT001813
HMDB IDHMDB0015684
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDiloxanide
Chemspider ID18400
ChEBI ID4601
PubChem Compound ID19529
Kegg Compound IDC07637
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10703963
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11411943
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11680811
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=11929661
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=14602387
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=15081350
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=1520794
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=16055294
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=16867415
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=16867588
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=18486369
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=21394273
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=2193407
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=22165007
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=23770637
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=23807049
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=26952868
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=2874011
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=28758845
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=4350466
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=8500812
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=8713754
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=9135682
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=9178149
25. 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.