Diloxanide

Last updated
Diloxanide furoate
Diloxanide furoate.svg
Clinical data
Trade names Furamide
AHFS/Drugs.com Micromedex Detailed Consumer Information
Pregnancy
category
  • No available data
Routes of
administration 		by mouth
ATC code
Legal status
Legal status
  • CA:Not approved
  • US:Not approved
Pharmacokinetic data
Bioavailability 90% (diloxanide)
Metabolism Hydrolyzed to furoic acid and diloxanide, which undergoes extensive glucuronidation
Elimination half-life 3 hours
Excretion Kidney (90%), fecal (10%)
Identifiers
  • 4-[(Dichloroacetyl)(methyl)amino]phenyl furan-2-carboxylate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.008.583 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C14H11Cl2NO4
Molar mass 328.15 g·mol−1
3D model (JSmol)
Melting point 112.5 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 Yes check.svgY
  • Key:BDYYDXJSHYEDGB-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (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]

Contents

Diloxanide generally has mild side effects. [3] Side effects may include flatulence, vomiting, and itchiness. [1] During pregnancy it is recommended that it be taken after the first trimester. [1] It is a luminal amebicide meaning that it only works on infections within the intestines. [2]

Diloxanide came into medical use in 1956. [3] It is on the World Health Organization's List of Essential Medicines. [4] It is not commercially available in much of the 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]

Related Research Articles

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<span class="mw-page-title-main">Metronidazole</span> Antibiotic and antiprotozoal medication

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<i>Entamoeba histolytica</i> Anaerobic parasitic protist

Entamoeba histolytica is an anaerobic parasitic amoebozoan, part of the genus Entamoeba. Predominantly infecting humans and other primates causing amoebiasis, E. histolytica is estimated to infect about 35-50 million people worldwide. E. histolytica infection is estimated to kill more than 55,000 people each year. Previously, it was thought that 10% of the world population was infected, but these figures predate the recognition that at least 90% of these infections were due to a second species, E. dispar. Mammals such as dogs and cats can become infected transiently, but are not thought to contribute significantly to transmission.

<span class="mw-page-title-main">Giardiasis</span> Parasitic disease that results in diarrhea

Giardiasis is a parasitic disease caused by Giardia duodenalis. Infected individuals who experience symptoms may have diarrhoea, abdominal pain, and weight loss. Less common symptoms include vomiting and blood in the stool. Symptoms usually begin one to three weeks after exposure and, without treatment, may last two to six weeks or longer.

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Entamoeba coli is a non-pathogenic species of Entamoeba that frequently exists as a commensal parasite in the human gastrointestinal tract. E. coli is important in medicine because it can be confused during microscopic examination of stained stool specimens with the pathogenic Entamoeba histolytica. This amoeba does not move much by the use of its pseudopod, and creates a "sur place (non-progressive) movement" inside the large intestine. Usually, the amoeba is immobile, and keeps its round shape. This amoeba, in its trophozoite stage, is only visible in fresh, unfixed stool specimens. Sometimes the Entamoeba coli have parasites as well. One is the fungus Sphaerita spp. This fungus lives in the cytoplasm of the E. coli. While this differentiation is typically done by visual examination of the parasitic cysts via light microscopy, new methods using molecular biology techniques have been developed. The scientific name of the amoeba, E. coli, is often mistaken for the bacterium, Escherichia coli. Unlike the bacterium, the amoeba is mostly harmless, and does not cause as many intestinal problems as some strains of the E. coli bacterium. To make the naming of these organisms less confusing, "alternate contractions" are used to name the species for the purpose making the naming easier; for example, using Esch. coli and Ent. coli for the bacterium and amoeba, instead of using E. coli for both.

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<span class="mw-page-title-main">Tinidazole</span> Chemical compound

Tinidazole, sold under the brand name Tindamax among others, is a medication used against protozoan infections. It is widely known throughout Europe and the developing world as a treatment for a variety of anaerobic amoebic and bacterial infections. It was developed in 1972 and is a prominent member of the nitroimidazole antibiotic class.

<span class="mw-page-title-main">Paromomycin</span> Chemical compound

Paromomycin is an antimicrobial used to treat a number of parasitic infections including amebiasis, giardiasis, leishmaniasis, and tapeworm infection. It is a first-line treatment for amebiasis or giardiasis during pregnancy. Otherwise, it is generally a second line treatment option. It is taken by mouth, applied to the skin, or by injection into a muscle.

Dientamoebiasis is a medical condition caused by infection with Dientamoeba fragilis, a single-cell parasite that infects the lower gastrointestinal tract of humans. It is an important cause of traveler's diarrhea, chronic abdominal pain, chronic fatigue, and failure to thrive in children.

Antiprotozoal agents is a class of pharmaceuticals used in treatment of protozoan infection.

Antiparasitics are a class of medications which are indicated for the treatment of parasitic diseases, such as those caused by helminths, amoeba, ectoparasites, parasitic fungi, and protozoa, among others. Antiparasitics target the parasitic agents of the infections by destroying them or inhibiting their growth; they are usually effective against a limited number of parasites within a particular class. Antiparasitics are one of the antimicrobial drugs which include antibiotics that target bacteria, and antifungals that target fungi. They may be administered orally, intravenously or topically. Overuse or misuse of antiparasitics can lead to the development of antimicrobial resistance.

<span class="mw-page-title-main">Nitazoxanide</span> Broad-spectrum antiparasitic and antiviral medication

Nitazoxanide, sold under the brand name Alinia among others, is a broad-spectrum antiparasitic and broad-spectrum antiviral medication that is used in medicine for the treatment of various helminthic, protozoal, and viral infections. It is indicated for the treatment of infection by Cryptosporidium parvum and Giardia lamblia in immunocompetent individuals and has been repurposed for the treatment of influenza. Nitazoxanide has also been shown to have in vitro antiparasitic activity and clinical treatment efficacy for infections caused by other protozoa and helminths; evidence as of 2014 suggested that it possesses efficacy in treating a number of viral infections as well.

<span class="mw-page-title-main">Protozoan infection</span> Parasitic disease caused by a protozoan

Protozoan infections are parasitic diseases caused by organisms formerly classified in the kingdom Protozoa. They are usually contracted by either an insect vector or by contact with an infected substance or surface and include organisms that are now classified in the supergroups Excavata, Amoebozoa, SAR, and Archaeplastida.

An amebicide is an agent that is destructive to amoeba, especially parasitic amoeba that cause amoebiasis.

<span class="mw-page-title-main">Amoebiasis</span> Human disease caused by amoeba protists

Amoebiasis, or amoebic dysentery, is an infection of the intestines caused by a parasitic amoeba Entamoeba histolytica. Amoebiasis can be present with no, mild, or severe symptoms. Symptoms may include lethargy, loss of weight, colonic ulcerations, abdominal pain, diarrhea, or bloody diarrhea. Complications can include inflammation and ulceration of the colon with tissue death or perforation, which may result in peritonitis. Anemia may develop due to prolonged gastric bleeding.

Entamoeba polecki is an intestinal parasite of the genus Entamoeba. E. polecki is found primarily in pigs and monkeys and is largely considered non-pathogenic in humans, although there have been some reports regarding symptomatic infections of humans. Prevalence is concentrated in New Guinea, with distribution also recorded in areas of southeast Asia, France, and the United States.

Entamoeba moshkovskii is part of the genus Entamoeba. It is found in areas with polluted water sources, and is prevalent in places such as Malaysia, India, and Bangladesh, but more recently has made its way to Turkey, Australia, and North America. This amoeba is said to rarely infect humans, but recently this has changed. It is in question as to whether it is pathogenic or not. Despite some sources stating this is a free living amoeba, various studies worldwide have shown it contains the ability to infect humans, with some cases of pathogenic potential being reported. Some of the symptoms that often occur are diarrhea, weight loss, bloody stool, and abdominal pain. The first known human infection also known as the "Laredo strain" of Entamoebic mushkovskii was in Laredo, Texas in 1991, although it was first described by a man named Tshalaia in 1941 in Moscow, Russia. It is known to affect people of all ages and genders.

References

  1. 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.
  2. 1 2 3 4 5 6 Farthing MJ (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. S2CID   19657328.
  3. 1 2 Hellgren U, Ericsson O, AdenAbdi Y, Gustafsson LL (2003). Handbook of Drugs for Tropical Parasitic Infections. CRC Press. p. 57. ISBN   9780203211519. Archived from the original on 2016-12-20.
  4. 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.
  5. 1 2 3 4 Griffin PM (2012). "Chapter 181: Diloxanide furoate". In Grayson ML (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.
  6. 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.
  7. ↑ McAuley JB, Herwaldt BL, Stokes SL, Becher JA, Roberts JM, Michelson MK, Juranek DD (September 1992). "Diloxanide furoate for treating asymptomatic Entamoeba histolytica cyst passers: 14 years' experience in the United States". Clinical Infectious Diseases. 15 (3): 464–468. doi:10.1093/clind/15.3.464. PMID   1520794.
  8. ↑ Arcangelo VP, Peterson AM (2006). "Parasitic Diseases". Pharmacotherapeutics For Advanced Practice: A Practical Approach. Lippincott Williams and Wilkins. pp.  441. ISBN   978-0-7817-5784-3.
  9. ↑ Gupta YK, Gupta M, Aneja S, Kohli K (January 2004). "Current drug therapy of protozoal diarrhoea". Indian Journal of Pediatrics. 71 (1): 55–58. doi:10.1007/BF02725657. PMID   14979387. S2CID   39637437.
  10. 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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