Diloxanide

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Diloxanide
Clinical data
Trade namesFuramide
AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
administration		by mouth
ATC code
Pharmacokinetic data
Bioavailability90% (diloxanide)
MetabolismHydrolyzed to furoic acid and diloxanide, which undergoes extensive glucuronidation
Elimination half-life3 hours
ExcretionKidney (90%), fecal (10%)
Identifiers
  • 4-[(Dichloroacetyl)(methyl)amino]phenyl furan-2-carboxylate
JSmol)
Melting point112.5 to 114 °C (234.5 to 237.2 °F)
  • O=C(Oc1ccc(N(C(=O)C(Cl)Cl)C)cc1)c2occc2
  • 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
 ☒NcheckY (what is this?)  (verify)

Diloxanide is a medication used to treat

amoeba infections.[1] In places where infections are not common, it is a second line treatment after paromomycin when a person has no symptoms.[2] For people who are symptomatic, it is used after treatment with metronidazole or tinidazole.[2] It is taken by mouth.[1]

Diloxanide generally has mild side effects.

intestines.[2]

Diloxanide came into medical use in 1956.

developed world as of 2012.[5]

Medical uses

Diloxanide furoate works only in the digestive tract and is a lumenal amebicide.[2][6] 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.[2][7] Paromomycin is considered the first line treatment for these cases.[citation needed]

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.[2][8]

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.[6] [why?]

Diloxanide furoate is not recommended in women who are breast feeding, and in children <2 years of age.[5]

Pharmacology

Diloxanide furoate destroys

trophozoites of E. histolytica and prevents amoebic cyst formation.[9] The exact mechanism of diloxanide is unknown.[10] Diloxanide is structurally related to chloramphenicol and may act in a similar fashion by disrupting the ribosome[5]

The prodrug, diloxanide furoate, is metabolized in the gastrointestinal tract to release the active drug, diloxanide.[10]

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

Society and culture

It is on the World Health Organization's List of Essential Medicines.[4]

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.[5]

References

  1. ^
    ISBN 9789241547659
    .
  2. ^
    S2CID 19657328
    .
  3. ^
    ISBN 9780203211519. Archived
    from the original on 20 December 2016.
  4. ^
    hdl:10665/325771
    . WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  5. ^
    ISBN 9781444147520. Archived
    from the original on 10 September 2017.
  6. ^
    ISBN 92-4-140104-4. Archived
    from the original on 12 September 2016.
  7. PMID 1520794
    .
  8. ISBN 978-0-7817-5784-3
    .
  9. S2CID 39637437
    .
  10. ^ a b c "Diloxanide 500 mg Tablets - Summary of Product Characteristics". UK Electronic Medicines Compendium. 31 March 2015. Archived from the original on 11 November 2016. Retrieved 11 November 2016.
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