Triclabendazole sulfoxide

Names

[ Name ]:
Triclabendazole sulfoxide

[Synonym ]:
Tcbz-SX
Triclabendazole sulfoxide
1H-Benzimidazole,6-chloro-5-(2,3-dichlorophenoxy)-2-(methylsulfinyl)
5-chloro-6-(2,3-dichlorophenoxy)-2-methylsulfinyl-1H-benzimidazole
triclabendazole sulphoxide

Biological Activity

[Description]:

Triclabendazole sulfoxide (TCBZ-SO) is the main plasma metabolite of Triclabendazole, and exhibits anti-parasite effects. Triclabendazole sulfoxide can inhibit membrane transporter ABCG2/BCRP[1][2].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Membrane Transporter/Ion Channel >> BCRP

[References]

[1]. Barrera B, et, al. The anthelmintic triclabendazole and its metabolites inhibit the membrane transporter ABCG2/BCRP. Antimicrob Agents Chemother. 2012 Jul;56(7):3535-43.

[2]. Robinson MW, et, al. The comparative metabolism of triclabendazole sulphoxide by triclabendazole-susceptible and triclabendazole-resistant Fasciola hepatica. Parasitol Res. 2004 Feb;92(3):205-10.

Chemical & Physical Properties

[ Density]:
1.69

[ Boiling Point ]:
547.6ºC at 760 mmHg

[ Molecular Formula ]:
C₁₄H₉Cl₃N₂O₂S

[ Molecular Weight ]:
375.65700

[ Flash Point ]:
285ºC

[ Exact Mass ]:
373.94500

[ PSA ]:
74.19000

[ LogP ]:
5.91850

[ Vapour Pressure ]:
4.81E-12mmHg at 25°C

[ Index of Refraction ]:
1.749

[ Storage condition ]:
2-8°C

Safety Information

[ Hazard Statements ]:
H413

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Fasciola hepatica: disruption of the vitelline cells in vitro by the sulphoxide metabolite of triclabendazole.

Parasitol. Res. 82(4) , 333-9, (1996)

The effects of the active sulphoxide metabolite of the fasciolicide triclabendazole (Fasinex, Ciba-Geigy) on the vitelline cells of Fasciola hepatica were determined in vitro by transmission electron ...

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...

Fasciola gigantica: tegumental surface alterations following treatment in vitro with the sulphoxide metabolite of triclabendazole.

Parasitol. Res. 88(4) , 315-25, (2002)

The effect of the active sulphoxide metabolite of the fasciolicide triclabendazole on the surface morphology of the tropical liver fluke, Fasciola gigantica, was determined in vitro by scanning electr...