Diloxanide furoate
Identification
- Generic Name
- Diloxanide furoate
- DrugBank Accession Number
- DB14638
- Background
Not Available
- Type
- Small Molecule
- Groups
- Approved
- Structure
- Weight
- Average: 328.147
Monoisotopic: 327.006513259 - Chemical Formula
- C14H11Cl2NO4
- Synonyms
- 2,2-dichloroacetamido-4-n-methylphenyl 2-furoate
- 4-(n-methyl-2,2-dichloroacetamido)phenyl 2-furoate
- Dichlofurazol
- Diloxanide furoate
- Diloxanidi furoas
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.
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- 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
- Adverse Effects
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- Toxicity
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
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Active Moieties
Name Kind UNII CAS InChI Key Diloxanide prodrug 89134SCM7M 579-38-4 GZZZSOOGQLOEOB-UHFFFAOYSA-N
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- Alkyl chloride / Alkyl halide / Anilide / Aromatic heteromonocyclic compound / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Carboxylic acid ester / Furan / Furoic acid ester show 18 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- phenols, benzoate ester (CHEBI:4601)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- YP4N72IW34
- CAS number
- 3736-81-0
- 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
References
- General References
- 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. [Article]
- External Links
- Human Metabolome Database
- HMDB0015684
- KEGG Drug
- D02480
- KEGG Compound
- C07637
- ChemSpider
- 18400
- BindingDB
- 70295
- ChEBI
- 4601
- ChEMBL
- CHEMBL1334860
- ZINC
- ZINC000000001300
- Wikipedia
- Diloxanide
Clinical Trials
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
Property Value Source Water Solubility 0.0382 mg/mL ALOGPS logP 3.33 ALOGPS logP 3.08 Chemaxon logS -3.9 ALOGPS pKa (Strongest Acidic) 13.09 Chemaxon pKa (Strongest Basic) -3.1 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 59.75 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 78.21 m3·mol-1 Chemaxon Polarizability 30.28 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 172.4882992 predictedDarkChem Lite v0.1.0 [M-H]- 170.00365 predictedDeepCCS 1.0 (2019) [M+H]+ 172.9054992 predictedDarkChem Lite v0.1.0 [M+H]+ 172.36166 predictedDeepCCS 1.0 (2019) [M+Na]+ 173.0280992 predictedDarkChem Lite v0.1.0 [M+Na]+ 178.45482 predictedDeepCCS 1.0 (2019)
Drug created at September 01, 2018 18:34 / Updated at February 21, 2021 18:54