Diloxanide

Diloxanide furoate
Names
Trade namesFuramide
IUPAC name
  • 4-[(Dichloroacetyl)(methyl)amino]phenyl furan-2-carboxylate
Clinical data
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Pregnancy
category
  • No data
Routes of
use		by mouth
Defined daily dose1.5 gram[1]
External links
AHFS/Drugs.comMicromedex Detailed Consumer Information
Legal
Legal status
  • CA: Not approved
  • US: Not approved
Pharmacokinetics
Bioavailability90% (diloxanide)
MetabolismHydrolyzed to furoic acid and diloxanide, which undergoes extensive glucuronidation
Elimination half-life3 hours
ExcretionKidney (90%), fecal (10%)
Chemical and physical data
FormulaC14H11Cl2NO4
Molar mass328.15 g·mol−1
3D model (JSmol)
Melting point112.5 to 114 °C (234.5 to 237.2 °F)
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 checkY
  • Key:BDYYDXJSHYEDGB-UHFFFAOYSA-N checkY

Diloxanide is a medication used to treat amoeba infections.[2] In places where infections are not common, it is a second line treatment after paromomycin when a person has no symptoms.[3] For people who are symptomatic, it is used after treatment with metronidazole or tinidazole.[3] It is taken by mouth.[2]

Diloxanide generally has mild side effects.[4] Side effects may include flatulence, vomiting, and itchiness.[2] During pregnancy it is recommended that it be taken after the first trimester.[2] It is a luminal amebicide meaning that it only works on infections within the intestines.[3]

Diloxanide came into medical use in 1956.[4] It is on the World Health Organization's List of Essential Medicines.[5] It is not commercially available in much of the developed world as of 2012.[6]

Medical uses

Diloxanide furoate works only in the digestive tract and is a lumenal amebicide.[3][7] It is considered second line treatment for infection with amoebas when no symptoms are present but the person is passing cysts, in places where infections are not common.[3][8] Paromomycin is considered the first line treatment for these cases.

For people who are symptomatic, it is used after treatment with ambecides that can penetrate tissue, like metronidazole or tinidazole. Diloxanide is considered second-line, while paromomycin is considered first line for this use as well.[3][9]

Dosage

The defined daily dose is 1.5 gram (by mouth).[1]

Side 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.[7]

Diloxanide furoate is not recommended in women who are breast feeding, and in children <2 years of age.[6]

Pharmacology

Diloxanide furoate destroys trophozoites of E. histolytica and prevents amoebic cyst formation.[10] The exact mechanism of diloxanide is unknown.[11] Diloxanide is structurally related to chloramphenicol and may act in a similar fashion by blocking protein synthesis.[6]

The prodrug, diloxanide furoate, is metabolized in the gastrointestinal tract to release the active drug, diloxanide.[11]

90% of each dose is excreted in the urine and the other 10% is excreted in the feces.[11]

Society and culture

It is on the World Health Organization's List of Essential Medicines.[5]

The drug was discovered by Boots UK in 1956, and introduced as Furamide; it was not available in much of the developed world as of 2012.[6]

References

  1. 1 2 "WHOCC - ATC/DDD Index". www.whocc.no. Archived from the original on 8 August 2020. Retrieved 21 September 2020.
  2. 1 2 3 4 World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. pp. 179, 587. hdl:10665/44053. ISBN 9789241547659.
  3. 1 2 3 4 5 6 Farthing, Michael JG (August 2006). "Treatment options for the eradication of intestinal protozoa". Nature Clinical Practice Gastroenterology & Hepatology. 3 (8): 436–445. doi:10.1038/ncpgasthep0557. PMID 16883348.
  4. 1 2 Hellgren, Urban; Ericsson, Orjan; AdenAbdi, Yakoub; Gustafsson, Lars L. (2003). Handbook of Drugs for Tropical Parasitic Infections. CRC Press. p. 57. ISBN 9780203211519. Archived from the original on 2016-12-20.
  5. 1 2 World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  6. 1 2 3 4 Griffin, Paul M (2012). "Chapter 181: Diloxanide furoate". In Grayson, M. Lindsay (ed.). Kucers' the use of antibiotics a clinical review of antibacterial, antifungal, antiparasitic and antiviral drugs (6th ed.). Boca Raton, Florida: CRC Press. p. 2121. ISBN 9781444147520. Archived from the original on 2017-09-10.
  7. 1 2 "Protozoa: Amoebiasis and giardiasis: Diloxanide". WHO Model Prescribing Information: Drugs Used in Parasitic Diseases (2nd ed.). WHO. 1995. ISBN 92-4-140104-4. Archived from the original on 2016-09-12.
  8. ↑ 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.
  9. ↑ Arcangelo, Virginia Poole (2006). Pharmacotherapeutics For Advanced Practice: A Practical Approach. Lippincott Williams and Wilkins. pp. 441. ISBN 978-0-7817-5784-3.
  10. ↑ Gupta, Y. K.; Gupta, Madhur; Aneja, S.; Kohli, K. (January 2004). "Current drug therapy of protozoal diarrhoea". The Indian Journal of Pediatrics. 71 (1): 55–58. doi:10.1007/BF02725657. PMID 14979387.
  11. 1 2 3 "Diloxanide 500 mg Tablets - Summary of Product Characteristics". UK Electronic Medicines Compendium. March 31, 2015. Archived from the original on 11 November 2016. Retrieved 11 November 2016.
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