DrugBank: Diloxanide (DB08792)

Identification

Name

Diloxanide

Accession Number

DB08792

Type

small molecule

Groups

approved

Description

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.

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Diloxanide furoate

Salts

Not Available

Brand names

Not Available

Brand mixtures

Not Available

Categories

Not Available

CAS number

3736-81-0

Weight

Average: 328.147
Monoisotopic: 327.006513259

Chemical Formula

C₁₄H₁₁Cl₂NO₄

InChI Key

InChIKey=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

Plain Text

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

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Not Available

Classes

Not Available

Substructures

Not Available

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

Protozoa

Pathways

Not Available

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

solid

Experimental Properties

Property	Value	Source
logP	2.24	DUTTA,H ET AL. (1988)

Predicted Properties

Property	Value	Source
water solubility	3.82e-02 g/l	ALOGPS
logP	3.33	ALOGPS
logP	3.08	ChemAxon
logS	-3.9	ALOGPS
pKa (strongest acidic)	13.09	ChemAxon
pKa (strongest basic)	-4.7	ChemAxon
physiological charge	0	ChemAxon
hydrogen acceptor count	2	ChemAxon
hydrogen donor count	0	ChemAxon
polar surface area	59.75	ChemAxon
rotatable bond count	5	ChemAxon
refractivity	78.21	ChemAxon
polarizability	30.28	ChemAxon

References

Synthesis Reference

Not Available

General Reference

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. Williams and T.L. Lemke, #Foye’s Principles of Medicinal Chemistry (fifth ed), Lippincott Williams & Wilkins, Baltimore (2002), p. 872.www.ncbi.nlm.nih.gov/pubmed/1520794

External Links

Resource	Link
ChemSpider	18400
PharmGKB	PA165958413
Drugs.com	http://www.drugs.com/mmx/diloxanide-furoate.html
Wikipedia	http://en.wikipedia.org/wiki/Diloxanide_furoate

ATC Codes

P01AC01

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Not Available

Food Interactions

Not Available

Comments

Drug created on September 20, 2010 08:58 / Updated on February 08, 2013 16:27