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Revision as of 16:11, 9 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 468954004 of page Diloxanide_furoate for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CAS_number').  Latest revision as of 03:53, 24 December 2024 edit Whywhenwhohow (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers49,181 edits infobox 
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{{Short description|Medication for amoebic gut infections}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Use dmy dates|date=March 2024}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
| verifiedrevid = 460788866 | verifiedrevid = 470454750
⚫ | IUPAC_name = 4-phenyl furan-2-carboxylate
| image = Diloxanide furoate.svg | image = Diloxanide furoate.svg
| drug_name = Diloxanide | alt =


<!--Clinical data--> <!--Clinical data-->
| tradename = Entamide | tradename = Furamide
| Drugs.com = {{drugs.com|CONS|diloxanide}} | Drugs.com = {{drugs.com|CONS|diloxanide}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫ | pregnancy_category =
| pregnancy_US = <!-- A / B / C / D / X -->
⚫ | routes_of_administration = ]
⚫ | pregnancy_category = No available data
⚫ | ATC_prefix = P01
⚫ | ATC_suffix = AC01
| ATC_supplemental = {{ATC|P01|AB52}}, {{ATC|P01|AB53}}

| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> | legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_CA_comment = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> | legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_US_comment = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status =
| legal_status = Not approved <small>(], ])</small>
⚫ | routes_of_administration = Oral


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = 90% (diloxanide) | bioavailability = 90% (diloxanide)
| protein_bound = | protein_bound =
| metabolism = ] to furoic acid and diloxanide, which undergoes extensive ] | metabolism = ] to furoic acid and diloxanide, which undergoes extensive ]
| elimination_half-life = 3 hours | elimination_half-life = 3 hours
| excretion = ] (90%), fecal (10%) | excretion = ] (90%), fecal (10%)


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}} | CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = <!-- blanked - oldvalue: 3736-81-0 --> | CAS_number = 3736-81-0
⚫ | ATC_prefix = P01
⚫ | ATC_suffix = AC01
| PubChem = 19529 | PubChem = 19529
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB08792 | DrugBank = DB14638
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 18400 | ChemSpiderID = 18400
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = YP4N72IW34
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D02480 | KEGG = D02480
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 1334860 --> | ChEMBL = 1334860

⚫ | C=14 | H=11 | Cl=2 | N=1 | O=4
<!--Chemical data-->
| molecular_weight = 328.147 g/mol
⚫ | IUPAC_name = 4-phenyl furan-2-carboxylate
⚫ | C=14 | H=11 | Cl=2 | N=1 | O=4
| smiles = O=C(Oc1ccc(N(C(=O)C(Cl)Cl)C)cc1)c2occc2 | 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_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 | 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_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BDYYDXJSHYEDGB-UHFFFAOYSA-N | StdInChIKey = BDYYDXJSHYEDGB-UHFFFAOYSA-N
| melting_point = 112.5
| melting_high = 114
}} }}

<!-- Definition and medical uses -->
'''Diloxanide''' is a medication used to treat ].<ref name=WHO2008/> In places where infections are not common, it is a second line treatment after ] when a person has no symptoms.<ref name=Nat2006rev/> For people who are symptomatic, it is used after treatment with ] or ].<ref name=Nat2006rev/> It is taken ].<ref name=WHO2008/>

<!-- Side effects and mechanism -->
Diloxanide generally has mild side effects.<ref name=Hell2003/> Side effects may include ], vomiting, and itchiness.<ref name=WHO2008/> During ] it is recommended that it be taken after the ].<ref name=WHO2008>{{cite book | title = WHO Model Formulary 2008 | year = 2009 | isbn = 9789241547659 | vauthors = ((World Health Organization)) | veditors = Stuart MC, Kouimtzi M, Hill SR | hdl = 10665/44053 | author-link = World Health Organization | publisher = World Health Organization | hdl-access=free |pages=179, 587 }}</ref> It is a ] meaning that it only works on infections within the ].<ref name=Nat2006rev>{{cite journal | vauthors = Farthing MJ | title = Treatment options for the eradication of intestinal protozoa | journal = Nature Clinical Practice. Gastroenterology & Hepatology | volume = 3 | issue = 8 | pages = 436–445 | date = August 2006 | pmid = 16883348 | doi = 10.1038/ncpgasthep0557 | s2cid = 19657328 }}</ref>

<!-- Society and culture -->
Diloxanide came into medical use in 1956.<ref name=Hell2003>{{cite book| vauthors = Hellgren U, Ericsson O, AdenAbdi Y, Gustafsson LL |title=Handbook of Drugs for Tropical Parasitic Infections|date=2003|publisher=CRC Press|isbn=9780203211519|page=57|url=https://books.google.com/books?id=DYc7bY-egLEC&pg=PA57|language=en|url-status=live|archive-url=https://web.archive.org/web/20161220074428/https://books.google.ca/books?id=DYc7bY-egLEC&pg=PA57|archive-date=20 December 2016}}</ref> It is on the ].<ref name="WHO21st">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref> It is not commercially available in much of the ] as of 2012.<ref name=Kucers2012>{{cite book| vauthors = Griffin PM | veditors = Grayson ML |title=Kucers' the use of antibiotics a clinical review of antibacterial, antifungal, antiparasitic and antiviral drugs|date=2012|publisher=CRC Press|location=Boca Raton, Florida|isbn=9781444147520|page=2121|edition=6th|chapter-url=https://books.google.com/books?id=XR3cBQAAQBAJ&pg=PA2121|chapter=Chapter 181: Diloxanide furoate|url-status=live|archive-url=https://web.archive.org/web/20170910151801/https://books.google.com/books?id=XR3cBQAAQBAJ&pg=PA2121|archive-date=10 September 2017}}</ref>

== Medical uses ==
Diloxanide furoate works only in the digestive tract and is a ].<ref name=Nat2006rev/><ref name=WHOmodel1995>{{cite book|title=WHO Model Prescribing Information: Drugs Used in Parasitic Diseases|date=1995|publisher=WHO|isbn=92-4-140104-4|edition=2nd|chapter-url=http://apps.who.int/medicinedocs/en/d/Jh2922e/2.1.2.html|chapter=Protozoa: Amoebiasis and giardiasis: Diloxanide|url-status=live|archive-url=https://web.archive.org/web/20160912214427/http://apps.who.int/medicinedocs/en/d/Jh2922e/2.1.2.html|archive-date=12 September 2016}}</ref> It is considered second line treatment for ] when no symptoms are present but the person is passing cysts, in places where infections are not common.<ref name=Nat2006rev/><ref name="pmid1520794">{{cite journal | vauthors = McAuley JB, Herwaldt BL, Stokes SL, Becher JA, Roberts JM, Michelson MK, Juranek DD | title = Diloxanide furoate for treating asymptomatic Entamoeba histolytica cyst passers: 14 years' experience in the United States | journal = Clinical Infectious Diseases | volume = 15 | issue = 3 | pages = 464–468 | date = September 1992 | pmid = 1520794 | doi = 10.1093/clind/15.3.464 }}</ref> ] is considered the first line treatment for these cases.{{cn|date=December 2022}}

For people who are symptomatic, it is used after treatment with ambecides that can penetrate tissue, like ] or ]. Diloxanide is considered second-line, while paromomycin is considered first line for this use as well.<ref name=Nat2006rev/><ref>{{Cite book | chapter = Parasitic Diseases |title=Pharmacotherapeutics For Advanced Practice: A Practical Approach| vauthors = Arcangelo VP, Peterson AM |publisher=Lippincott Williams and Wilkins|year=2006|isbn=978-0-7817-5784-3|pages=| chapter-url=https://archive.org/details/pharmacotherapeu02edunse/page/441}}</ref>

==Adverse effects==
Side effects include flatulence, itchiness, and hives. In general, the use of diloxanide is well tolerated with minimal toxicity. Although there is no clear risk of harm when used during pregnancy, diloxanide should be avoided in the first trimester if possible.<ref name=WHOmodel1995/> {{why?|date=December 2022}}

Diloxanide furoate is not recommended in women who are breast feeding, and in children <2 years of age.<ref name=Kucers2012/>

== Pharmacology ==
Diloxanide furoate destroys ] of ''E. histolytica'' and prevents amoebic cyst formation.<ref name=Gupta2004rev>{{cite journal | vauthors = Gupta YK, Gupta M, Aneja S, Kohli K | title = Current drug therapy of protozoal diarrhoea | journal = Indian Journal of Pediatrics | volume = 71 | issue = 1 | pages = 55–58 | date = January 2004 | pmid = 14979387 | doi = 10.1007/BF02725657 | s2cid = 39637437 }}</ref> The exact mechanism of diloxanide is unknown.<ref name=UKlabel2015/> Diloxanide is structurally related to chloramphenicol and may act in a similar fashion by disrupting the ]<ref name=Kucers2012/>

The ], diloxanide furoate, is metabolized in the gastrointestinal tract to release the active drug, diloxanide.<ref name=UKlabel2015>{{cite web|title=Diloxanide 500 mg Tablets - Summary of Product Characteristics|url=https://www.medicines.org.uk/emc/medicine/10787|publisher=UK Electronic Medicines Compendium|access-date=11 November 2016|date=31 March 2015|url-status=dead|archive-url=https://web.archive.org/web/20161111191427/https://www.medicines.org.uk/emc/medicine/10787|archive-date=11 November 2016}}</ref>

90% of each dose is excreted in the urine and the other 10% is excreted in the feces.<ref name=UKlabel2015/>

==Society and culture==
It is on the ].<ref name="WHO21st" />

The drug was discovered by ] in 1956, and introduced as ''Furamide''; it was not available in much of the developed world as of 2012.<ref name=Kucers2012/>

== References ==
{{Reflist}}

{{Agents against amoebozoa}}
{{Portal bar | Medicine}}

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