Triclabendazole | CAS#68786-66-3

MedKoo Cat#: 526271 | Name: Triclabendazole

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Triclabendazole is an anthelmintic and fasciolicidal, binding to beta-tubulin and preventing the polymerization of the microtubules of which they are part. Studies in vitro and/or in infected animals suggest that triclabendazole and its active metabolites (sulfoxide and sulfone) are absorbed by the tegument of the immature and mature worms, leading to a decrease of the resting membrane potential, inhibition of tubulin function as well as protein and enzyme synthesis. These metabolic disturbances are associated with inhibition of motility, disruption of the surface as well as ultrastructure that includes inhibition of spermatogenesis and vitelline cells.

Chemical Structure

Triclabendazole

CAS#68786-66-3

Theoretical Analysis

MedKoo Cat#: 526271

Name: Triclabendazole

CAS#: 68786-66-3

Chemical Formula: C14H9Cl3N2OS

Exact Mass: 357.9501

Molecular Weight: 359.65

Elemental Analysis: C, 46.76; H, 2.52; Cl, 29.57; N, 7.79; O, 4.45; S, 8.91

Price and Availability

Size	Price	Availability
1g	USD 250.00	2 Weeks
5g	USD 450.00	2 Weeks
10g	USD 650.00	2 Weeks

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Related CAS #

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Synonym

Triclabendazole; EGA230B; EGA-230B; EGA 230B; Fasinex; NVP-EGA230; NVP-EGA 230; NVP-EGA-230; CGA 89317; CGA-89317; CGA89317; Egaten.

IUPAC/Chemical Name

6-Chloro-5-(2,3-dichlorophenoxy)-2-methylsulfanyl-1H-benzimidazole

InChi Key

NQPDXQQQCQDHHW-UHFFFAOYSA-N

InChi Code

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)

SMILES Code

CSC1=NC2=CC(OC3=CC=CC(Cl)=C3Cl)=C(Cl)C=C2N1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Triclabendazole was approved for medical use in the United States in 2019. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. For human use it can also be obtained from the World Health Organization. It is also used in other animals.

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 359.65 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Real D, Orzan L, Leonardi D, Salomon CJ. Improving the Dissolution of Triclabendazole from Stable Crystalline Solid Dispersions Formulated for Oral Delivery. AAPS PharmSciTech. 2019 Dec 5;21(1):16. doi: 10.1208/s12249-019-1551-4. PubMed PMID: 31807963. 2: Gandhi P, Schmitt EK, Chen CW, Samantray S, Venishetty VK, Hughes D. Triclabendazole in the treatment of human fascioliasis: a review. Trans R Soc Trop Med Hyg. 2019 Dec 1;113(12):797-804. doi: 10.1093/trstmh/trz093. PubMed PMID: 31638149; PubMed Central PMCID: PMC6906998. 3: Ramadan HK, Hassan WA, Elossily NA, Ahmad AA, Mohamed AA, Abd-Elkader AS, Abdelsalam EMN, Khojah HMJ. Evaluation of nitazoxanide treatment following triclabendazole failure in an outbreak of human fascioliasis in Upper Egypt. PLoS Negl Trop Dis. 2019 Sep 25;13(9):e0007779. doi: 10.1371/journal.pntd.0007779. eCollection 2019 Sep. PubMed PMID: 31553716; PubMed Central PMCID: PMC6779272. 4: Viviani P, Lifschitz AL, Luque SE, Lloberas MM, Maté ML, Cardozo PA, Lanusse CE, Virkel GL. Pharmacologic interaction between oxfendazole and triclabendazole: In vitro biotransformation and systemic exposure in sheep. Exp Parasitol. 2019 Sep;204:107718. doi: 10.1016/j.exppara.2019.107718. Epub 2019 Jun 12. PubMed PMID: 31201779. 5: Mollinedo S, Gutierrez P, Azurduy R, Valle F, Salas A, Mollinedo Z, Soto P, Villarroel CF, Ransom J, Lawrence R, Berman J, Soto J. Mass Drug Administration of Triclabendazole for Fasciola Hepatica in Bolivia. Am J Trop Med Hyg. 2019 Jun;100(6):1494-1497. doi: 10.4269/ajtmh.19-0060. PubMed PMID: 31115295; PubMed Central PMCID: PMC6553894. 6: P A AS, S M A A. Immature Fasciola gigantica: Time-dependent ultrastructural changes following in vivo treatment with triclabendazole. Acta Trop. 2019 Aug;196:15-21. doi: 10.1016/j.actatropica.2019.04.015. Epub 2019 Apr 24. PubMed PMID: 31028722. 7: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006-. Available from http://www.ncbi.nlm.nih.gov/books/NBK539279/ PubMed PMID: 30933456. 8: Romero J, Villaguala C, Quiroz F, Landaeta-Aqueveque C, Alfaro G, Pérez R. Flukicide efficacy against Fasciola hepatica of Triclabendazole and Nitroxynil in cattle of the central valley of Chile. Rev Bras Parasitol Vet. 2019 Jan-Mar;28(1):164-167. doi: 10.1590/S1984-296120180089. Epub 2019 Mar 11. PubMed PMID: 30892461. 9: Gilbert G, MacGillivray FS, Robertson HL, Jonsson NN. Adverse effects of routine bovine health treatments containing triclabendazole and synthetic pyrethroids on the abundance of dipteran larvae in bovine faeces. Sci Rep. 2019 Mar 13;9(1):4315. doi: 10.1038/s41598-019-40800-6. PubMed PMID: 30867487; PubMed Central PMCID: PMC6416274. 10: Kamaludeen J, Graham-Brown J, Stephens N, Miller J, Howell A, Beesley NJ, Hodgkinson J, Learmount J, Williams D. Lack of efficacy of triclabendazole against Fasciola hepatica is present on sheep farms in three regions of England, and Wales. Vet Rec. 2019 Apr 20;184(16):502. doi: 10.1136/vr.105209. Epub 2019 Mar 1. PubMed PMID: 30824600; PubMed Central PMCID: PMC6583106. 11: Maté L, Giantin M, Viviani P, Ballent M, Tolosi R, Lifschitz A, Lanusse C, Dacasto M, Virkel G. Effects of fenbendazole and triclabendazole on the expression of cytochrome P450 1A and flavin-monooxygenase isozymes in bovine precision-cut liver slices. Vet J. 2019 Mar;245:61-69. doi: 10.1016/j.tvjl.2019.01.001. Epub 2019 Jan 15. PubMed PMID: 30819427. 12: Kikuchi H, Sakai T, Okura T, Nemoto S, Akiyama H. Total determination of triclabendazole and its metabolites in bovine tissues using liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2019 Mar 1;1109:54-59. doi: 10.1016/j.jchromb.2019.01.021. Epub 2019 Jan 28. PubMed PMID: 30721796. 13: Real D, Hoffmann S, Leonardi D, Salomon C, Goycoolea FM. Chitosan-based nanodelivery systems applied to the development of novel triclabendazole formulations. PLoS One. 2018 Dec 12;13(12):e0207625. doi: 10.1371/journal.pone.0207625. eCollection 2018. PubMed PMID: 30540811; PubMed Central PMCID: PMC6291145. 14: Giri P, Gupta L, Naidu S, Joshi V, Patel N, Giri S, Srinivas NR. In Vitro Drug-Drug Interaction Potential of Sulfoxide and/or Sulfone Metabolites of Albendazole, Triclabendazole , Aldicarb, Methiocarb, Montelukast and Ziprasidone. Drug Metab Lett. 2018;12(2):101-116. doi: 10.2174/1872312812666180816164626. PubMed PMID: 30117405; PubMed Central PMCID: PMC6416464. 15: Solana MV, Domínguez MF, Scarcella S, Radio S, Smircich P, Fernández S, Solana H, Tort JF. Different SNPs in Fasciola hepatica P-glycoprotein from diverse Latin American populations are not associated with Triclabendazole resistance. Mol Biochem Parasitol. 2018 Sep;224:57-60. doi: 10.1016/j.molbiopara.2018.07.005. Epub 2018 Jul 25. PubMed PMID: 30055185. 16: Hodgkinson JE, Cwiklinski K, Beesley N, Hartley C, Allen K, Williams DJL. Clonal amplification of Fasciola hepatica in Galba truncatula: within and between isolate variation of triclabendazole-susceptible and -resistant clones. Parasit Vectors. 2018 Jun 26;11(1):363. doi: 10.1186/s13071-018-2952-z. PubMed PMID: 29941045; PubMed Central PMCID: PMC6020221. 17: Real D, Leonardi D, Williams RO 3rd, Repka MA, Salomon CJ. Solving the Delivery Problems of Triclabendazole Using Cyclodextrins. AAPS PharmSciTech. 2018 Jul;19(5):2311-2321. doi: 10.1208/s12249-018-1057-5. Epub 2018 May 29. PubMed PMID: 29845501. 18: Viviani P, Lifschitz AL, Maté ML, García JP, Lanusse CE, Virkel GL. Assessment of the pharmacological interactions between the nematodicidal fenbendazole and the flukicidal triclabendazole: In vitro studies with bovine liver microsomes and slices. J Vet Pharmacol Ther. 2018 Jun;41(3):476-484. doi: 10.1111/jvp.12492. Epub 2018 Feb 21. PubMed PMID: 29465161. 19: Abdelaal MMO, Brennan GP, Hanna REB, Abdel-Aziz A, Fairweather I. Disruption of egg production by triclabendazole-resistant Fasciola hepatica following treatment with a commercial preparation of myrrh (Mirazid). Acta Parasitol. 2017 Jun 1;62(2):336-347. doi: 10.1515/ap-2017-0041. PubMed PMID: 28426420. 20: Ferretti R, Carradori S, Guglielmi P, Pierini M, Casulli A, Cirilli R. Enantiomers of triclabendazole sulfoxide: Analytical and semipreparative HPLC separation, absolute configuration assignment, and transformation into sodium salt. J Pharm Biomed Anal. 2017 Jun 5;140:38-44. doi: 10.1016/j.jpba.2017.03.021. Epub 2017 Mar 16. PubMed PMID: 28340473.