diloxanide
- CAS NO.:579-38-4
- Empirical Formula: C9H9Cl2NO2
- Molecular Weight: 234.08
- MDL number: MFCD00592507
- EINECS: 2094394
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-19 15:53:33
What is diloxanide?
The Uses of diloxanide
Diloxanide is also active against cysts and trophozoites localized in the lumen of the intestine, and it is used for treating the carrier E. histolytica, as well as for treating asymptomatic or moderate forms of amebiasis. In the transition stage to trophozoites, the drug is less active than iodoquinol. A synonym of this drug is furamide.
The Uses of diloxanide
Diloxanide is used for the treatment of amoebiasis which is an infection of the diegestive tract caused by amoebas of the entamoeba group.
Antimicrobial activity
Diloxanide inhibits E. histolytica with unusually high specificity at concentrations of 0.01–0.1 mg/L.
Acquired resistance
No resistance has been reported. Patients with dysentery have lower cure rates than cyst excreters.
Pharmaceutical Applications
Dichloro(hydroxyphenyl)methylacetamide. Available as an insoluble ester, the furoate, for oral administration.
Pharmacokinetics
Human pharmacokinetic data are limited. Animal data show that diloxanide furoate is rapidly absorbed from the intestine. The furoate is hydrolyzed in the gut, leaving high intraluminal concentrations of free diloxanide. About 75% is excreted via the kidney within 48 h, mostly as a glucuronide.
Clinical Use
Asymptomatic intestinal infection with E. histolytica
It is also used in invasive amebiasis in conjunction with
nitroimidazoles in order to eradicate luminal cysts.
Clinical Use
Furamide, or eutamide, is the 2-furoate ester of 2,2-dichloro-4 -hydroxy-N-methylacetanilide. It was developed as a resultof the discovery that various α,α-dichloroacetamidespossessed amebicidal activity in vitro. Diloxanide itself andmany of its esters are also active, and drug metabolism studiesindicate that hydrolysis of the amide is required for theamebicidal effect. Nonpolar esters of diloxanide are morepotent than polar ones. Diloxanide furoate has been used inthe treatment of asymptomatic carriers of E. histolytica. Itseffectiveness against acute intestinal amebiasis or hepaticabscesses, however, has not been established. Diloxanidefuroate is a white crystalline powder. It is administered orallyonly as 500-mg tablets and may be obtained in the UnitedStates from the CDC in Atlanta, Georgia.
Side Effects
It is well tolerated, but flatulence is common, and nausea and vomiting may occur.
Synthesis
Diloxanide, 2,2-dichloro-N-(4-furoyloxyphenyl)-N-methylacetamide (37.2.4), is made by acylating 2,2-dichloro-N-(4-hydroxyphenyl)-N-methylacetamide (37.2.3) with -2-furoyl chloride. The 2,2-dichloro-N-(4-hydroxyphenyl)-N-methylacetiamide (37.2.3) is made by N-acylating 4-hydroxy-N-methylaniline with either dichloroacetyl chloride, or by an extremely original method of using chloral cyanohydrin.
Properties of diloxanide
Melting point: | 175° |
Boiling point: | 356.2±42.0 °C(Predicted) |
Density | 1.439±0.06 g/cm3(Predicted) |
storage temp. | Store at -20°C |
solubility | DMSO:33.33(Max Conc. mg/mL);142.39(Max Conc. mM) |
form | Solid |
pka | 9.95±0.15(Predicted) |
color | Light brown to brown |
Safety information for diloxanide
Computed Descriptors for diloxanide
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