Diloxanide furoate: Difference between revisions

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__NOTOC__
{{Drugbox
{{CMG}}
| Verifiedfields = changed
| verifiedrevid = 470454750
| IUPAC_name = 4-[(dichloroacetyl)(methyl)amino]phenyl furan-2-carboxylate
| image = Diloxanide furoate.png
| drug_name = Diloxanide


==Overview==
<!--Clinical data-->
| tradename = Furamide
| Drugs.com = {{drugs.com|CONS|diloxanide}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B            / C / D / X -->
| pregnancy_category = No available data
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status = Not approved <small>([[United States|US]], [[Canada|CA]])</small>
| routes_of_administration = Oral


Diloxanide furoate is an anti-protozoal drug used in the treatment of [[Entamoeba histolytica]] and some other protozoal infections.
<!--Pharmacokinetic data-->
| bioavailability = 90% (diloxanide)
| protein_bound = 
| metabolism = [[hydrolysis|Hydrolyzed]] to furoic acid and diloxanide, which undergoes extensive [[glucuronidation]]
| elimination_half-life = 3 hours
| excretion = [[Kidney|Renal]] (90%), fecal (10%)


==Category==
<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 3736-81-0
| ATC_prefix = P01
| ATC_suffix = AC01
| PubChem = 19529
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB08792
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 18400
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D02480
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1334860


Antiparasitic
<!--Chemical data-->
 
| C=14 | H=11 | Cl=2 | N=1 | O=4
==US Brand Names==
| molecular_weight = 328.147 g/mol
 
| smiles = O=C(Oc1ccc(N(C(=O)C(Cl)Cl)C)cc1)c2occc2
ENTAMIDE, FUMARIDE (not available in the U.S.)
| InChI = 1/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
 
| InChIKey = BDYYDXJSHYEDGB-UHFFFAOYAB
==Prescribing Information==
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
 
| StdInChI = 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
===Therapeutic indications===
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
For the treatment of acute and chronic intestinal [[amebiasis]].
| StdInChIKey = BDYYDXJSHYEDGB-UHFFFAOYSA-N
===Administration===
}}
 
__NOTOC__
Adults: One tablet three times daily for ten days.
{{SI}}
 
{{CMG}}
Children: 20 mg/kg bodyweight daily in divided doses for ten days. Furamide is not suitable for use in children weighing less than 25 kg.
==Overview==
 
'''Diloxanide furoate''' is a luminal amebicide used in the treatment of ''[[Amebiasis]].'' 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 US. In India it is available as ''Amicline'' by ''Franco-Indian''.
Elderly: There is no need for dosage reduction in the elderly.
 
If required, a second course of treatment may be prescribed.
 
===Contraindications===
[[Hypersensitivity]] to diloxanide furoate.
 
===Precautions===
 
Keep all medicines out of the reach of children.
 
===Drug Interactions===
 
No clinically-significant drug interactions known.
 
===Pregnancy and Lactation===
 
The safety of Furamide during pregnancy and lactation has not been established and use during these periods should therefore be avoided.
 
===Adverse Effects===
 
No serious side effects have been reported and the bacterial flora of the gut is not upset. Flatulence sometimes occurs but may usually be disregarded. Occasionally, vomiting, pruritus and urticaria may occur.
 
===Overdosage===
 
Furamide tablets are unlikely to constitute a hazard in overdosage. In severe overdosage, early gastric lavage is recommended. There is no specific antidote. Treatment should be symptomatic and supportive.
 
===Clinical Pharmacology===
 
In the gut, diloxanide furoate is largely, if not wholly, hydrolysed into diloxanide and furoic acid under the combined action of bacterial and gut esterases. After absorption, diloxanide is very rapidly conjugated to form a glucuronide. In circulating blood, it is present to about 99% as a glucuronide and 1% as free diloxanide. Diloxanide is predominantly excreted in the urine. It is believed that the unabsorbed diloxanide is the active anti-amoebic substance, up to 10% remaining in the gut which is subsequently excreted as diloxanide in the faeces.
 
==Mechanism of Action==
 
Diloxanide furoate is a luminal amoebicide acting principally in the bowel lumen, although its mode of action is not known.
 
==Safety and Effectiveness==
 
A 13-year study conducted by the United States [[Center for Disease Control]] between 1977 and 1990 found that this drug had a low incidence of side effects and was successful in treatment of 86% of asymptomatic carriers of ''[[Entamoeba histolytica]].'' <ref name="pmid1520794">{{cite journal |author=McAuley JB, Herwaldt BL, Stokes SL, ''et al'' |title=Diloxanide furoate for treating asymptomatic Entamoeba histolytica cyst passers: 14 years' experience in the United States |journal=Clin. Infect. Dis. |volume=15 |issue=3 |pages=464–8 |year=1992 |pmid=1520794 |doi=}}</ref>


==Availability==
<!-- Society and culture -->
It is on the [[World Health Organization's List of Essential Medicines]], a list of the most important medication needed in a basic [[health system]].


A [[CDC]] study authorized the use of this drug in the treatment of 4,371 cases of ''[[Entamoeba histolytica]]'' from 1977 to 1990.  <ref name="pmid1520794" />  
==Safety and effectiveness==
A 13-year study conducted by the United States [[Center for Disease Control]] between 1977 and 1990 found that this drug had a low incidence of side effects and was successful in treatment of 86% of asymptomatic carriers of ''[[Entamoeba histolytica]].''   


==References==
==References==
{{Reflist|2}}
{{Reflist|2}}


[[Category:Antibiotics]]
[[Category:Antiprotozoal agents]]
[[Category:Wikinfect]]
[[Category:Drug]]

Latest revision as of 13:04, 23 April 2015

Diloxanide
Clinical data
Trade namesFuramide
AHFS/Drugs.comMicromedex Detailed Consumer Information
Pregnancy
category
  • No available data
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • Not approved (US, CA)
Pharmacokinetic data
Bioavailability90% (diloxanide)
MetabolismHydrolyzed to furoic acid and diloxanide, which undergoes extensive glucuronidation
Elimination half-life3 hours
ExcretionRenal (90%), fecal (10%)
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
KEGG
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC14H11Cl2NO4
Molar mass328.147 g/mol
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Diloxanide furoate is a luminal amebicide used in the treatment of Amebiasis. 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 US. In India it is available as Amicline by Franco-Indian.

It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.

Safety and effectiveness

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

References

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