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Diloxanide

Diloxanide structure

CAS No:
579-38-4
Formula:
C9H9Cl2NO2
Chemical Name:
Diloxanide
Synonyms:
Acetamide,2,2-dichloro-N-(4-hydroxyphenyl)-N-methyl-;Acetanilide,2,2-dichloro-4′-hydroxy-N-methyl-;2,2-Dichloro-N-(4-hydroxyphenyl)-N-methylacetamide;N-Dichloroacetyl-N-methyl-p-hydroxyaniline;2,2-Dichloro-4′-hydroxy-N-methylacetanilide;Dichloro-N-4-hydroxyphenyl-N-methylacetamide;Entamide;Diloxanide;Amebamida;Ame-boots;Diloxanid;RD 3803
Categories:
Active Pharmaceutical Ingredients > Antiparasitic Drugs

Description

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.

Diloxanide Basic Attributes

Molecular Weight：

234.081

Exact Mass：

234.08

EC Number：

209-439-4

UNII：

89134SCM7M

DSSTox ID：

DTXSID0022939

ATC Code：

P - Antiparasitic products, insecticides and repellents

Characteristics

PSA：

40.5

XLogP3：

2.24

Density：

1.439g/cm3

Melting Point：

175 °C

Boiling Point：

356.2ºC at 760 mmHg

Flash Point：

169.2ºC

Refractive Index：

1.615

Drug Information

Drug 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.

Pharmacology：

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.

MeSH：

Agents which are destructive to amebae, especially the parasitic species causing AMEBIASIS in man and animal. (See all compounds classified as Amebicides.)

Absorption：

Bioavailability is 90% (in diloxanide parental form), however diloxanide furoate is slowly absorbed from the gastrointestinal tract.|Renal (90%, rapidly excreted as glucuronide metabolite). 10% is excreted in the feces as diloxanide.

Metabolism/Metabolites：

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).

Biological Half-Life：

3 hours

Mechanism of Action：

Unknown. Diloxanide may inhibit protein synthesis.

MeSH Entry Terms：

2,2-dichloro-4'-hydroxy-N-methylacetanilide 2-furoate

Diloxanide Use and Manufacturing

Dichloro(hydroxyphenyl)methylacetamide. Available as an insoluble ester, the furoate, for oral administration.

Computed Properties

Molecular Weight:234.08
XLogP3:2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:233.0010339
Monoisotopic Mass:233.0010339
Topological Polar Surface Area:40.5
Heavy Atom Count:14
Complexity:203
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes