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Home > Encyclopedia > Diloxanide furoate

Diloxanide furoate

Diloxanide furoate structure

Diloxanide furoate 

structure
  • CAS No:

    3736-81-0

  • Formula:

    C14H11Cl2NO4

  • Chemical Name:

    Diloxanide furoate

  • Synonyms:

    2-Furancarboxylic acid,4-[(2,2-dichloroacetyl)methylamino]phenyl ester;2-Furoic acid,ester with 2,2-dichloro-4′-hydroxy-N-methylacetanilide;2-Furancarboxylic acid,4-[(dichloroacetyl)methylamino]phenyl ester;Furoic acid,ester with 2,2-dichloro-4′-hydroxy-N-methylacetanilide;Acetanilide,2,2-dichloro-4′-hydroxy-N-methyl-,2-furoate (ester);8073 CB;Dichlofurazol;Entamide furoate;Entamide 2-furoate;4-Hydroxy-N-methyl dichloroacetanilide 2-furoate;Furamide (amebicide);Furamide;Diloxanide furoate;Diloxanid furoate;Amebiazol;Diclofurazol;Furentomin;Histomibal;Miforon

Description

Diloxanide furoate is a luminal amebicide used in the treatment of Amebiasis, is considered the luminal agent of choice for mild intestinal amebiasis or asymptomatic cyst carriers.


Solid


Diloxanide furoate is a carboxylic ester resulting from the formal condensation of the carboxy group of furan-2-carboxylic acid with the hydroxy group of 2,2-dichloro-N-(4-hydroxyphenyl)-N-methylacetamide. It is a drug used for the treatment of asymptomatic amebiasis. It has a role as an antiamoebic agent and a prodrug. It is a member of furans, a carboxylic ester, a tertiary carboxamide and an organochlorine compound.

Diloxanide furoate Basic Attributes

328.15

328.15

223-108-1

YP4N72IW34

759146

DTXSID8048999

2924296000

Characteristics

59.8

3.26530

Solid

1.424±0.06 g/cm3(Predicted)

111-114 °C

>49.2 [ug/mL]

171.7 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

NONH for all modes of transport

3

22

36

LV1821800

Xn

P264, P270, P301+P312, P330, P501

H302

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 40 companies from 1 notifications to the ECHA C&L Inventory.

Drug Information

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.

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.

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

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.

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).

3 hours

Unknown. Diloxanide may inhibit protein synthesis.

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

Diloxanide furoate Use and Manufacturing

Antidiarrhoeals / Antiprotozoles

Computed Properties

Molecular Weight:328.1
XLogP3:3.4
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:327.0065132
Monoisotopic Mass:327.0065132
Topological Polar Surface Area:59.8
Heavy Atom Count:21
Complexity:383
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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