TriclabendazoleCAS# 68786-66-3 |
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Quality Control & MSDS
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| Cas No. | 68786-66-3 | SDF | Download SDF |
| PubChem ID | 50248 | Appearance | Powder |
| Formula | C14 H9Cl3N2OS | M.Wt | 359.66 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Synonyms | CGA89317 | ||
| Solubility | DMSO : 100 mg/mL (278.04 mM; Need ultrasonic) | ||
| Chemical Name | 6-chloro-5-(2,3-dichlorophenoxy)-2-methylsulfanyl-1H-benzimidazole | ||
| SMILES | CSC1=NC2=CC(=C(C=C2N1)Cl)OC3=C(C(=CC=C3)Cl)Cl | ||
| Standard InChIKey | NQPDXQQQCQDHHW-UHFFFAOYSA-N | ||
| Standard 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) | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Triclabendazole(CGA89317) is a benzimidazole, it binds to tubulin impairing intracellular transport mechanisms and interferes with protein synthesis.
Target: Microtubule/Tubulin
Triclabendazole 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]. References: | |||||
Triclabendazole Dilution Calculator
Triclabendazole Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.7804 mL | 13.902 mL | 27.804 mL | 55.6081 mL | 69.5101 mL |
| 5 mM | 0.5561 mL | 2.7804 mL | 5.5608 mL | 11.1216 mL | 13.902 mL |
| 10 mM | 0.278 mL | 1.3902 mL | 2.7804 mL | 5.5608 mL | 6.951 mL |
| 50 mM | 0.0556 mL | 0.278 mL | 0.5561 mL | 1.1122 mL | 1.3902 mL |
| 100 mM | 0.0278 mL | 0.139 mL | 0.278 mL | 0.5561 mL | 0.6951 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Triclabendazole is a benzimidazole, it binds to tubulin impairing intracellular transport mechanisms and interferes with protein synthesis.
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Novel triclabendazole prodrug: A highly water soluble alternative for the treatment of fasciolosis.[Pubmed:28027870]
Bioorg Med Chem Lett. 2017 Feb 1;27(3):616-619.
In this work we present the synthesis, aqueous solubility and stability, hydrolysis by alkaline phosphatase, and in vivo fasciolicidal activity in sheep of a highly water soluble phosphate salt prodrug of Triclabendazole (MFR-5). The aqueous solubility of MFR-5 at pH 7 was 88,000-fold that of Triclabendazole. MFR-5 showed excellent aqueous stability (>95% after 26h) at pH 7, making it ideal for developing pharmaceutical compositions in the form of solutions that can easily be hydrolyzed by the enzyme alkaline phosphatase (t=13.6s) to liberate the precursor compound. An aqueous solution of MFR-5 administered intramuscularly to sheep at concentrations of 4, 6 and 8mg/kg presented a fasciolicidal efficiency of 96.5%, 98.4% and 99.2%, respectively. In the in vivo experiments, MFR-5 reduced 100% the excretion of eggs in all of the above concentrations.
Re-infection with Fasciola gigantica 6-month post-treatment with triclabendazole in cattle from mobile pastoralist husbandry systems at Lake Chad.[Pubmed:27884440]
Vet Parasitol. 2016 Oct 30;230:43-48.
At Lake Chad in central Africa, livestock fascioliasis caused by Fasciola gigantica represents a major veterinary health problem, particularly in cattle reared in mobile pastoralist husbandry systems. We assessed re-infection after a single dose of Triclabendazole with fascioliasis in cattle in a mobile pastoralist setting towards the end of the dry season. Within the cattle herds of 14 groups of mobile pastoralists, 375 cattle were randomly selected. A faecal sample was obtained from each animal to determine the prevalence of F. gigantica. Animals were administered a single oral dose of Triclabendazole (12mg/kg). A second faecal sample was obtained 6-month post-treatment after cattle had returned from the annual migration cycle. Faecal samples were fixed in sodium acetate-acetic acid-formalin (SAF), and examined for F. gigantica using the sedimentation technique. From the 375 cattle enrolled at baseline, 198 animals (53%) in 12 groups of mobile pastoralists were re-sampled at the 6-month follow-up. Baseline prevalence did not differ noteworthy between animals lost to follow-up and those re-examined. At baseline, bovine fascioliasis prevalence in cattle with follow-up data was 41.9% (95% confidence interval (CI) 35.2-48.9%). At the 6-month post-treatment follow-up, the prevalence was 46.0% (95% CI 39.2-52.9%), ranging between 0% and 75% at the herd level. The mean faecal egg counts at the unit of the herd were higher at follow-up compared to baseline. The observed persistent high prevalence of F. gigantica infection in cattle shows that a single pre-rainy season treatment does not prevent rapid re-infection despite the partial migration away from the high-risk areas at Lake Chad into drier areas. A locally adapted strategic control package for fascioliasis in cattle in the Lake Chad area ought to integrate targeted Triclabendazole treatment and seasonal transhumance practices.
Simultaneous extraction and determination of albendazole and triclabendazole by a novel syringe to syringe dispersive liquid phase microextraction-solidified floating organic drop combined with high performance liquid chromatography.[Pubmed:27286766]
Anal Chim Acta. 2016 Aug 17;932:22-8.
A syringe to syringe dispersive liquid phase microextraction-solidified floating organic drop was introduced and used for the simultaneous extraction of trace amounts of albendazole and Triclabendazole from different matrices. The extracted analytes were determined by high performance liquid chromatography along with fluorescence detection. The analytical parameters affecting the microextraction efficiency including the nature and volume of the extraction solvent, sample volume, sample pH, ionic strength and the cycles of extraction were optimized. The calibration curves were linear in the range of 0.1-30.0 mug L(-1) and 0.2-30.0 mug L(-1) with determination coefficients of 0.9999 and 0.9998 for albendazole and Triclabendazole respectively. The detection limits defined as three folds of the signal to noise ratio were found to be 0.02 mug L(-1) for albendazole and 0.06 mug L(-1) for Triclabendazole. The inter-day and intra-day precision (RSD%) for both analytes at three concentration levels (0.5, 2.0 and 10.0 mug L(-1)) were in the range of 6.3-10.1% and 5.0-7.5% respectively. The developed method was successfully applied to determine albendazole and Triclabendazole in water, cow milk, honey, and urine samples.
Enantiomers of triclabendazole sulfoxide: Analytical and semipreparative HPLC separation, absolute configuration assignment, and transformation into sodium salt.[Pubmed:28340473]
J Pharm Biomed Anal. 2017 Jun 5;140:38-44.
Direct HPLC separation of the enantiomers of Triclabendazole sulfoxide (TCBZ-SO), which is the main metabolite of the anthelmintic drug Triclabendazole, was carried out using the polysaccharide-based Chiralpak AS-H and Chiralpak IF-3 chiral stationary phases (CSPs). The chromatographic behaviour of both CSPs was evaluated and compared using normal-phase and reversed-phase eluents at different column temperatures. The eluent mixture of n-hexane-2-propanol-trifluoroacetic acid 70:30:0.1 (v/v/v) and a column temperature of 40 degrees C were identified as the best operational conditions to carry out semipreparative enantioseparations on a 1-cm I.D. AS-H column. Under these conditions, 12.5mg of racemic sample were resolved in a single chromatographic run within 15min. Comparison of calculated and experimental chiroptical properties provided the absolute configuration assignment at the sulfur atom. The salification of the isolated enantiomers of TCBZ-SO by reaction with sodium hydroxide solution produced water-soluble Na salts which are potentially useful in the development of new anthelmintic enantiomerically pure formulations.
