Triclabendazole

Triclabendazole, sold under the brand name Egaten among others, is a medication used to treat fascioliasis and paragonimiasis.^[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]

Triclabendazole

Clinical data
Trade names	Fasinex, Egaten, others
AHFS/Drugs.com	Monograph
MedlinePlus	a619048
License data	US DailyMed: Triclabendazole
Routes of administration	By mouth
ATC code	P02BX04 (WHO) QP52AC01 (WHO)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Metabolism	Oxidation to sulfone and sulfoxide metabolites
Elimination half-life	22–24 hours
Excretion	Feces (>95%), urine (2%), milk (<1%)
Identifiers
IUPAC name 5-Chloro-6-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzimidazole
CAS Number	68786-66-3 N
PubChem CID	50248
DrugBank	DB12245 Y
ChemSpider	45565 Y
UNII	4784C8E03O
KEGG	D07364 N
ChEMBL	ChEMBL1086440 Y
CompTox Dashboard (EPA)	DTXSID7043952
ECHA InfoCard	100.127.414
Chemical and physical data
Formula	C14H9Cl3N2OS
Molar mass	359.65 g·mol−1
3D model (JSmol)	Interactive image
Melting point	175 to 176 °C (347 to 349 °F)
SMILES CSc3nc2cc(Cl)c(Oc1cccc(Cl)c1Cl)cc2[nH]3
InChI 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) Y Key:NQPDXQQQCQDHHW-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

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 during pregnancy, triclabendazole has not been studied well in this population.^[2] It is a member of the benzimidazole family of medications for worms.^[1]

Triclabendazole was approved for medical use in the United States in 2019.^[3][4] It is on the World 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

It is a member of the benzimidazole family of anthelmintics. The benzimidazole drugs share a common molecular structure, triclabendazole being the exception in having a chlorinated benzene ring but no carbamate group. Benzimidazoles such as triclabendazole are generally accepted to bind to beta-tubulin therefore preventing the polymerization of microtubules.^{[citation needed]}

History

Since late 1990s, triclabendazole became available as a generic 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% and ivermectin 0.6% solution, is designed to treat infections by Fasciola hepatica (both immature and adult liver 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

1. World 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. Wolfe 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. Retrieved 18 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. Retrieved 10 December 2016.

Further reading

• "Report of the WHO Informal Meeting on use of triclabendazole in fascioliasis control" (PDF). World Health Organization (WHO). 2006.