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Identification
NameDiloxanide
Accession NumberDB08792
TypeSmall Molecule
GroupsApproved
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
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Diloxanide furoate
3736-81-0
Thumb
  • InChI Key: BDYYDXJSHYEDGB-UHFFFAOYSA-N
  • Monoisotopic Mass: 327.006513259
  • Average Mass: 328.147
DBSALT001813
Categories
UNII89134SCM7M
CAS number579-38-4
WeightAverage: 234.08
Monoisotopic: 233.0010339
Chemical FormulaC9H9Cl2NO2
InChI KeyGZZZSOOGQLOEOB-UHFFFAOYSA-N
InChI
InChI=1S/C9H9Cl2NO2/c1-12(9(14)8(10)11)6-2-4-7(13)5-3-6/h2-5,8,13H,1H3
IUPAC Name
2,2-dichloro-N-(4-hydroxyphenyl)-N-methylacetamide
SMILES
CN(C(=O)C(Cl)Cl)C1=CC=C(O)C=C1
Pharmacology
IndicationDiloxanide is used alone as a primary agent in the treatment of asymptomatic (cyst passers) intestinal amebiasis caused by Entamoeba histolytica. Diloxanide may also be used concurrently, or sequentially, with other agents such as the nitroimidazoles (eg. metronidazole) in the treatment of invasive or extraintestinal forms of amebiasis.
Structured Indications Not Available
PharmacodynamicsDiloxanide is a luminal amebicide, however the mechanism of action of diloxanide is unknown. Diloxanide destroys the trophozoites of E. histolytica that eventually form into cysts. The cysts are then excreted by persons infected with asymptomatic amebiasis. Diloxanide furoate is a prodrug, and is hydrolyzed in the gastrointestinal tract to produce diloxanide, the active ingredient.
Mechanism of actionUnknown. Diloxanide may inhibit protein synthesis.
Related Articles
AbsorptionBioavailability is 90% (in diloxanide parental form), however diloxanide furoate is slowly absorbed from the gastrointestinal tract.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hydrolyzed to furoic acid and diloxanide, which undergoes extensive glucuronidation (99% of diloxanide occurs as glucuronide and 1% as free diloxanide in the systemic circulation).

Route of eliminationRenal (90%, rapidly excreted as glucuronide metabolite). 10% is excreted in the feces as diloxanide.
Half life3 hours
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Protozoa
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
References
Synthesis ReferenceNot 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 ]
External Links
ATC CodesP01AC01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9454
Blood Brain Barrier+0.9784
Caco-2 permeable+0.5558
P-glycoprotein substrateNon-substrate0.8705
P-glycoprotein inhibitor INon-inhibitor0.9364
P-glycoprotein inhibitor IINon-inhibitor0.7636
Renal organic cation transporterNon-inhibitor0.8958
CYP450 2C9 substrateNon-substrate0.7021
CYP450 2D6 substrateNon-substrate0.8229
CYP450 3A4 substrateSubstrate0.585
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8944
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5266
Ames testAMES toxic0.538
CarcinogenicityNon-carcinogens0.7816
BiodegradationNot ready biodegradable0.8478
Rat acute toxicity2.2608 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9924
hERG inhibition (predictor II)Non-inhibitor0.9271
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP2.24DUTTA,H ET AL. (1988)
Predicted Properties
PropertyValueSource
Water Solubility2.31 mg/mLALOGPS
logP2.01ALOGPS
logP2.05ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)9.39ChemAxon
pKa (Strongest Basic)-5.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area40.54 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity55.99 m3·mol-1ChemAxon
Polarizability20.9 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAnilides
Direct ParentAnilides
Alternative Parents
Substituents
  • Anilide
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Alkyl chloride
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Alkyl halide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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Drug created on September 20, 2010 08:58 / Updated on August 17, 2016 12:24