Diloxanide

Diloxanide furoate

Systematic (IUPAC) name
4-[(Dichloroacetyl)(methyl)amino]phenyl furan-2-carboxylate
Clinical data
Trade names	Furamide
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy category	No available data
Routes of administration	Oral
Legal status
Legal status	Not approved (US, CA)
Pharmacokinetic data
Bioavailability	90% (diloxanide)
Metabolism	Hydrolyzed to furoic acid and diloxanide, which undergoes extensive glucuronidation
Biological half-life	3 hours
Excretion	Renal (90%), fecal (10%)
Identifiers
CAS Number	3736-81-0
ATC code	P01AC01 (WHO)
PubChem	CID 19529
DrugBank	DB08792
ChemSpider	18400
KEGG	D02480
ChEMBL	CHEMBL1334860
Chemical data
Formula	C14H11Cl2NO4
Molar mass	328.147 g/mol
SMILES O=C(Oc1ccc(N(C(=O)C(Cl)Cl)C)cc1)c2occc2
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 Key:BDYYDXJSHYEDGB-UHFFFAOYSA-N
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Diloxanide (INN) is a luminal amebicide used in the treatment of amebiasis.^[1] It is formulated as the furoate ester diloxanide furoate. It is considered the luminal agent of choice for mild intestinal amebiasis or asymptomatic cyst carriers. It can also be added to metronidazole (active drug in luminal and extraintestinal amebiasis) in acute amebic dysentery as well as hepatic abscess(In hepatic abscess it is for the control of cysts in the lumen which may cause relapse). The drug was discovered by The Boots Company Plc in 1956 and introduced as Furamide. The Furamide brand is now owned by Abbott Laboratories. It is not available in the United States. In India it is available as Amicline by Franco-Indian.

Diloxanide furoate is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.^[2]

Safety and effectiveness

A 13-year study conducted by the United States Center for Disease Control between 1977 and 1990 found that diloxanide furoate had a low incidence of side effects and was successful in treatment of 86% of asymptomatic carriers of Entamoeba histolytica.^[3]

References

1. Fernandes H, D'Souza CR, Swethadri GK, Naik CN (2009). "Ameboma of the colon with amebic liver abscess mimicking metastatic colon cancer". Indian J Pathol Microbiol 52 (2): 228–30. doi:10.4103/0377-4929.48927. PMID 19332922.
2. "WHO Model List of Essential Medicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.
3. McAuley JB, Herwaldt BL, Stokes SL; et al. (1992). "Diloxanide furoate for treating asymptomatic Entamoeba histolytica cyst passers: 14 years' experience in the United States". Clin. Infect. Dis. 15 (3): 464–8. doi:10.1093/clind/15.3.464. PMID 1520794.