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Enantiomers of Triclabendazole Sulfoxide: Analytical and Semipreparative HPLC Separation, Absolute Configuration Assignment, and Transformation Into Sodium Salt

Enantiomers of Triclabendazole Sulfoxide: Analytical and Semipreparative HPLC Separation, Absolute Configuration Assignment, and Transformation Into Sodium Salt

Rosella Ferretti, Simone Carradori, Paolo Guglielmi, Marco Pierini, Adriano Casulli, Roberto Cirilli

J Pharm Biomed Anal. 2017 Jun 5;140:38-44.

PMID: 28340473

Abstract:

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°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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP100648133	Triclabendazole sulfoxide		100648-13-3	Price

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