Diloxanide furoate

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

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Name
Diloxanide furoate
Accession Number
DB14638  (DBSALT001813)
Type
Small Molecule
Groups
Approved
Description
Not Available
Structure
Thumb
Synonyms
  • 2,2-dichloroacetamido-4-n-methylphenyl 2-furoate
  • 4-(n-methyl-2,2-dichloroacetamido)phenyl 2-furoate
  • Dichlofurazol
  • Diloxanidi furoas
Active Moieties
NameKindUNIICASInChI Key
Diloxanideprodrug89134SCM7M579-38-4GZZZSOOGQLOEOB-UHFFFAOYSA-N
Categories
UNII
YP4N72IW34
CAS number
3736-81-0
Weight
Average: 328.147
Monoisotopic: 327.006513259
Chemical Formula
C14H11Cl2NO4
InChI Key
BDYYDXJSHYEDGB-UHFFFAOYSA-N
InChI
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
IUPAC Name
4-(2,2-dichloro-N-methylacetamido)phenyl furan-2-carboxylate
SMILES
CN(C(=O)C(Cl)Cl)C1=CC=C(OC(=O)C2=CC=CO2)C=C1

Pharmacology

Indication

Diloxanide 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.

Pharmacodynamics

Diloxanide 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 action

Unknown. Diloxanide may inhibit protein synthesis.

Absorption

Bioavailability is 90% (in diloxanide parental form), however diloxanide furoate is slowly absorbed from the gastrointestinal tract.

Volume of distribution
Not Available
Protein binding
Not 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 elimination

Renal (90%, rapidly excreted as glucuronide metabolite). 10% is excreted in the feces as diloxanide.

Half life

3 hours

Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

References

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
Human Metabolome Database
HMDB0015684
KEGG Drug
D02480
KEGG Compound
C07637
ChemSpider
18400
BindingDB
70295
ChEBI
4601
ChEMBL
CHEMBL1334860
Wikipedia
Diloxanide

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0382 mg/mLALOGPS
logP3.33ALOGPS
logP3.08ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)13.09ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area59.75 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity78.21 m3·mol-1ChemAxon
Polarizability30.28 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-9321100000-2db11dd84428f82ca90e

Taxonomy

Description
This compound 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenol esters
Sub Class
Not Available
Direct Parent
Phenol esters
Alternative Parents
Furoic acid esters / Anilides / Phenoxy compounds / Tertiary carboxylic acid amides / Heteroaromatic compounds / Carboxylic acid esters / Oxacyclic compounds / Monocarboxylic acids and derivatives / Organopnictogen compounds / Organonitrogen compounds
show 5 more
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
show 18 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
phenols, benzoate ester (CHEBI:4601)

Drug created on September 01, 2018 12:34 / Updated on September 02, 2019 20:20