NAV

Diloxanide

Identification

Generic Name
Diloxanide
DrugBank Accession Number
DB08792
Background

Diloxanide (as 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.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 234.08
Monoisotopic: 233.0010339
Chemical Formula
C9H9Cl2NO2
Synonyms
  • Diloxanide
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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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Contraindications & Blackbox Warnings
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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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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

Categories

ATC Codes
P01AB52 — Metronidazole and diloxanideP01AC01 — Diloxanide
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Anilides
Direct Parent
Anilides
Alternative Parents
1-hydroxy-2-unsubstituted benzenoids / Tertiary carboxylic acid amides / Organopnictogen compounds / Organonitrogen compounds / Organochlorides / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds / Alkyl chlorides
Substituents
1-hydroxy-2-unsubstituted benzenoid / Alkyl chloride / Alkyl halide / Anilide / Aromatic homomonocyclic compound / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Hydrocarbon derivative / Organic nitrogen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
  • Protozoa

Chemical Identifiers

UNII
89134SCM7M
CAS number
579-38-4
InChI Key
GZZZSOOGQLOEOB-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

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. [Article]
PubChem Compound
11367
PubChem Substance
99445263
ChemSpider
10889
RxNav
67182
ChEMBL
CHEMBL2103768
ZINC
ZINC000000001299
PharmGKB
PA165958413
Drugs.com
Drugs.com Drug Page
Wikipedia
Diloxanide_furoate

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
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 RuleNoChemaxon
MDDR-like RuleNoChemaxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-00di-3900000000-9b0c7ba2020a88c95f96
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0190000000-73bc09a8ee3e30deac86
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-1090000000-177a8994aac2275182f8
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-053r-0970000000-0ef677b069391f93e188
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ul0-3900000000-9d4e1bda644817c70131
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-2900000000-e801ef93fc7c127217e2
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fl3-9800000000-993d56cfc76349841497
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-144.02618
predicted
DeepCCS 1.0 (2019)
[M+H]+146.42174
predicted
DeepCCS 1.0 (2019)
[M+Na]+152.63806
predicted
DeepCCS 1.0 (2019)

Drug created at September 20, 2010 14:58 / Updated at February 21, 2021 18:52