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Merck
CN

35391

Triclabendazole sulfoxide

VETRANAL®, analytical standard

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C14H9Cl3N2O2S
CAS Number:
100648-13-3
Molecular Weight:
375.66
Beilstein:
5829656
MDL number:
MFCD09038493
UNSPSC Code:
41116107
PubChem Substance ID:
329755152
NACRES:
NA.24

Key Documents

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grade

analytical standard

Quality Level

100

product line

VETRANAL®

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

forensics and toxicology
pharmaceutical (small molecule)

format

neat

SMILES string

CS(=O)c1nc2cc(Cl)c(Oc3cccc(Cl)c3Cl)cc2[nH]1

InChI

1S/C14H9Cl3N2O2S/c1-22(20)14-18-9-5-8(16)12(6-10(9)19-14)21-11-4-2-3-7(15)13(11)17/h2-6H,1H3,(H,18,19)

InChI key

GABQPFWIQFRJSE-UHFFFAOYSA-N

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General description

Triclabendazole sulfoxide belongs to the benzimidazole class of anthelmintics drugs. It is very much effective against mature and immature stages of Fasciola hepatica and Fasciola gigantica in all ruminant species.

Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Other Notes

Find a digital Reference Material for this product available on our online platform ChemisTwin® for NMR. You can use this digital equivalent on ChemisTwin® for your sample identity confirmation and compound quantification (with digital external standard). An NMR spectrum of this substance can be viewed and an online comparison against your sample can be performed with a few mouseclicks. Learn more here and start your free trial.

Legal Information

VETRANAL is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM8414
BCCL1071
BCCG3902
BCCD1858
BCCB5255

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L Mottier et al.
The Journal of parasitology, 92(6), 1355-1360 (2007-02-20)
Triclabendazole (TCBZ) and albendazole (ABZ) are flukicidal benzimidazole compounds extensively used in veterinary medicine. Although TCBZ has excellent activity against mature and immature stages of the liver fluke, Fasciola hepatica, ABZ action is restricted to flukes older than 12 wk.
A W Stitt et al.
Parasitology research, 79(7), 529-536 (1993-01-01)
The effects of the novel benzimidazole, triclabendazole (Fasinex, Ciba-Geigy), in its active sulphoxide metabolite form (TCBZ-SX), on the tegumental surface of Fasciola hepatica has been examined in vitro. The tegument of adult flukes incubated in TCBZ-SX (50 micrograms/ml) appeared swollen
Pharmacokinetic disposition of triclabendazole in cattle and sheep; discrimination of the order and the rate of the absorption process of its active metabolite triclabendazole sulfoxide
Mestorino.N, et al.
Veterinary Research Communications, 32, 21-33 (2008)
Interaction of anthelmintic drugs with P-glycoprotein in recombinant LLC-PK1-mdr1a cells
Dupuy J, et al.
Chemico-Biological Interactions, 186, 280-286 (2010)
Mark W Robinson et al.
Parasitology research, 92(3), 205-210 (2003-12-04)
Benzimidazole anthelmintics are widely used against nematode, cestode and trematode parasites. The drugs undergo several enzyme-mediated reactions within the host animal that produce a number of metabolites. Although it has been shown that certain helminths, including Fasciola hepatica, can metabolise
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