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Triclabendazole

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
Triclabendazole
Clinical data
Trade namesFasinex, Egaten, others
AHFS/Drugs.comMonograph
MedlinePlusa619048
License data
Routes of
administration
By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
MetabolismOxidation to sulfone and sulfoxide metabolites
Eliminationhalf-life22–24 hours
ExcretionFeces (>95%), urine (2%), milk (<1%)
Identifiers
  • 5-Chloro-6-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzimidazole
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.127.414Edit this at Wikidata
Chemical and physical data
FormulaC14H9Cl3N2OS
Molar mass359.65 g·mol−1
3D model (JSmol)
Melting point175 to 176 °C (347 to 349 °F)
  • CSc3nc2cc(Cl)c(Oc1cccc(Cl)c1Cl)cc2[nH]3
  • InChI=1S/C14H9Cl3N2OS/c1-21-14-18-9-5-8(16)12(6-10(9)19-14)20-11-4-2-3-7(15)13(11)17/h2-6H,1H3,(H,18,19) checkY
  • Key:NQPDXQQQCQDHHW-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Triclabendazole, sold under the brand nameEgaten among others, is a medication used to treatfascioliasis andparagonimiasis.[1] It is very effective for both conditions.[1] Treatment in hospital may be required.[1] It is taken by mouth with typically one or two doses being required.[1]

Side effects are generally few, but can include abdominal pain and headaches.[1]Biliary colic may occur due to dying worms.[2] While no harm has been found with use duringpregnancy, triclabendazole has not been studied well in this population.[2] It is a member of thebenzimidazole family ofmedications for worms.[1]

Triclabendazole was approved for medical use in the United States in 2019.[3][4] It is on theWorld Health Organization's List of Essential Medicines.[5] For human use, it can be obtained from the World Health Organization.[2] It is also used in animals.[6]

Chemistry

[edit]

It is a member of thebenzimidazole family ofanthelmintics. The benzimidazole drugs share a common molecular structure, triclabendazole being the exception in having a chlorinated benzene ring but nocarbamate group. Benzimidazoles such as triclabendazole are generally accepted to bind tobeta-tubulin therefore preventing the polymerization ofmicrotubules.[7]

History

[edit]

Since late 1990s, triclabendazole became available as ageneric drug, as patents expired in many countries. Many products were developed then. Among them, Trivantel 15, a 15% triclabendazole suspension, was launched by Agrovet Market Animal Health in the early 2000s. In 2009, the first triclabendazole injectable solution (combined with ivermectin) was developed and launched, also by Agrovet Market Animal Health. The product, Fasiject Plus, a triclabendazole 36% andivermectin 0.6% solution, is designed to treat infections byFasciola hepatica (both immature and adultliver flukes),roundworms and ectoparasites, as well.[citation needed]

Fasinex is a brand name for veterinary use while Egaten is a brand name for human use.[citation needed]

References

[edit]
  1. ^abcdefWorld Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.).WHO Model Formulary 2008. World Health Organization. pp. 94, 96.hdl:10665/44053.ISBN 9789241547659.
  2. ^abcWolfe MM, Lowe RC (2014)."Benzimidazoles".Pocket Guide to GastrointestinaI Drugs. John Wiley & Sons. p. PT173.ISBN 9781118481554.Archived from the original on 20 December 2016.
  3. ^"Drug Trials Snapshots: Egaten".U.S.Food and Drug Administration (FDA). 13 February 2019.
  4. ^"Egaten (triclabendazole)"(PDF).FDA. Archived fromthe original(PDF) on 2 October 2019. Retrieved18 February 2019.
  5. ^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. ^"Triclabendazole".Drugs.com.Archived from the original on 20 December 2016. Retrieved10 December 2016.
  7. ^Baksheeva VE, La Rocca R, Allegro D, Derviaux C, Pasquier E, Roche P, Morelli X, Devred F, Golovin AV, Tsvetkov PO (2025). "NanoDSF Screening for Anti-tubulin Agents Uncovers New Structure–Activity Insights".Journal of Medicinal Chemistry.doi:10.1021/acs.jmedchem.5c01008.

Further reading

[edit]
Antiplatyhelmintic agents
Antitrematodals
(schistosomicides)
Bindstubulin
AChE inhibitor
Other/unknown
Anticestodals
(taeniacides)
Bindstubulin
Other/unknown
Antinematodal agents
(including
macrofilaricides)
Bindstubulin
Glutamate-gated chloride channel,GABA receptor
NMDA
Other/unknown
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