triclabendazole

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 470613656

| IUPAC_name = 5-Chloro-6-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzimidazole

| image = Triclabendazole.svg

| image_class = skin-invert-image

| width = 215

| alt =

| image2 = Triclabendazole-from-xtal-3D-bs-17.png

| image_class2 = bg-transparent

| alt2 =

| tradename = Fasinex, Egaten, others

| Drugs.com = {{drugs.com|monograph|triclabendazole}}

| MedlinePlus = a619048

| DailyMedID = Triclabendazole

| pregnancy_category =

| routes_of_administration = By mouth

| ATC_prefix = P02

| ATC_suffix = BX04

| ATC_supplemental = {{ATCvet|P52|AC01}}

| legal_US = Rx-only

| legal_status =

| bioavailability =

| metabolism = Oxidation to sulfone and sulfoxide metabolites

| elimination_half-life = 22–24 hours

| excretion = Feces (>95%), urine (2%), milk (<1%)

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 68786-66-3

| PubChem = 50248

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB12245

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 45565

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 4784C8E03O

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1086440

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = D07364

| C=14 | H=9 | Cl=3 | N=2 | O=1 | S=1

| smiles = CSc3nc2cc(Cl)c(Oc1cccc(Cl)c1Cl)cc2[nH]3

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = NQPDXQQQCQDHHW-UHFFFAOYSA-N

| melting_point = 175

| melting_high = 176

}}

Triclabendazole, sold under the brand name Egaten among others, is a medication used to treat fascioliasis and paragonimiasis. It is very effective for both conditions. Treatment in hospital may be required. It is taken by mouth with typically one or two doses being required.{{cite book | title = WHO Model Formulary 2008 | year = 2009 | isbn = 9789241547659 | vauthors = ((World Health Organization)) | veditors = Stuart MC, Kouimtzi M, Hill SR | hdl = 10665/44053 | author-link = World Health Organization | publisher = World Health Organization | hdl-access=free |pages=94, 96 }}

Side effects are generally few, but can include abdominal pain and headaches. Biliary colic may occur due to dying worms. While no harm has been found with use during pregnancy, triclabendazole has not been studied well in this population. It is a member of the benzimidazole family of medications for worms.

Triclabendazole was approved for medical use in the United States in 2019.{{cite web | title=Drug Trials Snapshots: Egaten | website=U.S. Food and Drug Administration (FDA) | date=13 February 2019 | url=https://www.fda.gov/drugs/drug-approvals-and-databases/drug-trials-snapshots-egaten }}{{cite web |title=Egaten (triclabendazole) |url=https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/208711s000lbl.pdf |archive-url=https://web.archive.org/web/20191002232100/https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/208711s000lbl.pdf |url-status=dead |archive-date=2 October 2019 |website=FDA |access-date=18 February 2019}} It is on the World Health Organization's List of Essential Medicines.{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO }} For human use, it can be obtained from the World Health Organization.{{cite book| vauthors = Wolfe MM, Lowe RC |title=Pocket Guide to GastrointestinaI Drugs|publisher=John Wiley & Sons|isbn=9781118481554|page=PT173|date=2014|chapter-url=https://books.google.com/books?id=sUKMAgAAQBAJ&pg=PT173|language=en|chapter=Benzimidazoles|url-status=live|archive-url=https://web.archive.org/web/20161220081111/https://books.google.ca/books?id=sUKMAgAAQBAJ&pg=PT173|archive-date=20 December 2016}} It is also used in animals.{{cite web|title=Triclabendazole | work = Drugs.com |url= https://www.drugs.com/international/triclabendazole.html |access-date=10 December 2016|url-status=live|archive-url=https://web.archive.org/web/20161220224224/https://www.drugs.com/international/triclabendazole.html|archive-date=20 December 2016}}

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.{{cn|date=December 2022}}

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.{{cn|date=December 2022}}

Fasinex is a brand name for veterinary use while Egaten is a brand name for human use.{{cn|date=December 2022}}

triclabendazole

Chemistry

History

References

Further reading