CAS 68786-66-3|Triclabendazole
Introduction：Basic information about CAS 68786-66-3|Triclabendazole, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Triclabendazole | ||
|---|---|---|---|
| CAS Number | 68786-66-3 | Molecular Weight | 359.658 |
| Density | 1.6±0.1 g/cm3 | Boiling Point | 495.9±55.0 °C at 760 mmHg |
| Molecular Formula | C14H9Cl3N2OS | Melting Point | 175-176°C |
| MSDS | ChineseUSA | Flash Point | 253.7±31.5 °C |
Names
| Name | Triclabendazole |
|---|---|
| Synonym | More Synonyms |
Triclabendazole BiologicalActivity
| Description | Triclabendazole(CGA89317) is a benzimidazole, it binds to tubulin impairing intracellular transport mechanisms and interferes with protein synthesis.Target: Microtubule/TubulinTriclabendazole treatment produces percentage decreases of the fluke egg output by 15.3%, 4.3% and 36.6%, respectively, in sheep, dairy cows and heifers, these results indicate the presence of TCBZ-resistant Fasciola hepatica in sheep and cattle on this farm [1]. Triclabendazole sulphoxide (50 mg/mL) results in extensive damage to the tegument of triclabendazole-susceptible F. hepatica, whereas triclabendazole-resistant flukes shows only localized and relatively minor disruption of the tegument covering the spines [2].Triclabendazole is metabolized into a number of compounds, depending on the route of administration, plasma levels peak at 18-24 hours (Triclabendazole sulphoxide) and 36-48 hours (Triclabendazole sulphone), neither Triclabendazole nor any toher metabolites can be detected in plasma. Triclabendazole sulphoxide blocks the transport of secretory bodies from the cell body to the tegumental surface, the block occurs at the site of their formation by the Golgi complex in the cell body, in their movement through the cytoplasmic connections to the syncytium, and in their movement from the base to the apex of the syncytium. Triclabendazole binds to the colchicine binding site on the β-tubulin molecule and this has been used at the basis for evaluating the relative acitvity of Triclabendazole [3]. |
|---|---|
| Related Catalog | Signaling Pathways >>Cell Cycle/DNA Damage >>Microtubule/TubulinSignaling Pathways >>Cytoskeleton >>Microtubule/TubulinResearch Areas >>Infection |
| References | [1]. Moll, L., et al., Resistance of Fasciola hepatica against triclabendazole in cattle and sheep in The netherlands. Vet Parasitol, 2000. 91(1-2): p. 153-8. [2]. Robinson, M.W., et al., Triclabendazole-resistant Fasciola hepatica: beta-tubulin and response to in vitro treatment with triclabendazole. Parasitology, 2002. 124(Pt 3): p. 325-38. [3]. Fairweather, I., Triclabendazole: new skills to unravel an old(ish) enigma. J Helminthol, 2005. 79(3): p. 227-34. |
Chemical & Physical Properties
| Density | 1.6±0.1 g/cm3 |
|---|---|
| Boiling Point | 495.9±55.0 °C at 760 mmHg |
| Melting Point | 175-176°C |
| Molecular Formula | C14H9Cl3N2OS |
| Molecular Weight | 359.658 |
| Flash Point | 253.7±31.5 °C |
| Exact Mass | 357.950104 |
| PSA | 63.21000 |
| LogP | 5.97 |
| Vapour Pressure | 0.0±1.3 mmHg at 25°C |
| Index of Refraction | 1.724 |
| InChIKey | NQPDXQQQCQDHHW-UHFFFAOYSA-N |
| SMILES | CSc1nc2cc(Oc3cccc(Cl)c3Cl)c(Cl)cc2[nH]1 |
| Stability | Stability |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- >8 gm/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- MDACAP Medicamentos de Actualidad. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1965- Volume(issue)/page/year: 21,227,1985
- TYPE OF TEST :
- LC50 - Lethal concentration, 50 percent kill
- ROUTE OF EXPOSURE :
- Inhalation
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- >500 mg/m3/4H
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- MDACAP Medicamentos de Actualidad. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1965- Volume(issue)/page/year: 21,227,1985
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Administration onto the skin
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- >4 gm/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- MDACAP Medicamentos de Actualidad. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1965- Volume(issue)/page/year: 21,227,1985
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- >8 gm/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- MDACAP Medicamentos de Actualidad. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1965- Volume(issue)/page/year: 21,227,1985
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rabbit
- DOSE/DURATION :
- 206 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- MDACAP Medicamentos de Actualidad. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1965- Volume(issue)/page/year: 21,227,1985 ** REPRODUCTIVE DATA **
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 800 mg/kg
- SEX/DURATION :
- female 8-15 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
- REFERENCE :
- TXCYAC Toxicology. (Elsevier Scientific Pub. Ireland, Ltd., POB 85, Limerick, Ireland) V.1- 1973- Volume(issue)/page/year: 43,283,1987
Safety Information
| Hazard Statements | H413 |
|---|---|
| Personal Protective Equipment | Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter |
| Hazard Codes | Xn: Harmful; |
| Risk Phrases | R36/37/38 |
| Safety Phrases | S26-S36 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | 3 |
| RTECS | DD6747000 |
| HS Code | 2933990090 |
Customs
| HS Code | 2933990090 |
|---|---|
| Summary | 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0% |
Articles38
More Articles| Time-course and accumulation of triclabendazole and its metabolites in bile, liver tissues and flukes collected from treated sheep. Exp. Parasitol. 136 , 14-9, (2014) The flukicidal compound triclabendazole (TCBZ) has a complex metabolic pattern that includes the systemic presence of its sulphoxide (TCBZ.SO) and sulphone (TCBZ.SO2) metabolites, usually recovered fr... | |
| The anthelmintic triclabendazole and its metabolites inhibit the membrane transporter ABCG2/BCRP. Antimicrob. Agents Chemother. 56(7) , 3535-43, (2012) ABCG2/BCRP is an ATP-binding cassette transporter that extrudes compounds from cells in the intestine, liver, kidney, and other organs, such as the mammary gland, affecting pharmacokinetics and milk s... | |
| Isothermal microcalorimetry to study the activity of triclabendazole and its metabolites on juvenile and adult Fasciola hepatica. Exp. Parasitol. 133(3) , 265-8, (2013) Isothermal microcalorimetry (IMC) is an analytical tool that continuously measures the heat flow generated by chemical, physical or biological processes. We have demonstrated that IMC is a useful tool... |
Synonyms
| Fasinex |
| MFCD00864519 |
| Triclabendazole |
| 6-Chloro-5-(2,3-dichlorophenoxy)-2-methylthio-benzimidazole |
| 5-Chloro-6-(2,3-dichlorophenoxy)-2-(methylsulfanyl)-1H-benzimidazole |
| 1H-Benzimidazole, 6-chloro-5-(2,3-dichlorophenoxy)-2-(methylthio)- |
| 5-Chloro-6-(2,3-dichlorophenoxy)-2-methylthio-1H-benzimidazole |
