Diloxanide furoate: Difference between revisions

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


<!--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


<!--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%)


'''Diloxanide furoate''' is an anti-protozoal drug used in the treatment of [[Entamoeba histolytica]] and some other protozoal infections.
<!--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


==Safety and Effectiveness==
<!--Chemical data-->
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>
| C=14 | H=11 | Cl=2 | N=1 | O=4
| molecular_weight = 328.147 g/mol
| smiles = O=C(Oc1ccc(N(C(=O)C(Cl)Cl)C)cc1)c2occc2
| 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
| 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BDYYDXJSHYEDGB-UHFFFAOYSA-N
}}
__NOTOC__
{{SI}}
{{CMG}}
==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''.


==Availability by Country==
<!-- 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]].


'''United States''': Not currently approved for use.  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}}
{{Reflist|2}}
 
 
 
 
[[Category:Drugs]]


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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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