Enantiomeric separation of tapentadol by capillary electrophoresis-Study of chiral selectivity manipulation by various types of cyclodextrins

Joanna Znaleziona, Ida Fejos, Juraj Ševčík, Michal Douša, S. Béni, Vítězslav Maier

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

The chiral recognition of the centrally acting analgesic agent tapentadol and its isomers with various cyclodextrins (CDs) was studied by capillary electrophoresis, focusing on the migration order of four stereoisomers. In the case of non-charged hydroxypropylated CDs (2-hydroxypropyl-β-CD, 2-hydroxypropyl-γ-CD) the beta derivative was able to discriminate the S,R- and R,S-isomers in acidic background electrolyte, whereas the gamma allowed the separation of S,S- and R,R-tapentadol, respectively. Dual CD system containing both hosts was used to separate all of four isomers. Negatively charged sulfated-α-CD at 1.0% (w/v) concentration in 100. mM sodium borate buffer (pH 9.5) was capable of separating the isomers with favorable enantiomer migration order and the optimized method was able to determine 0.15% of chiral impurities of tapentadol in the presence of the last migrating clinically important R,R-isomer.

Original languageEnglish
Pages (from-to)10-16
Number of pages7
JournalJournal of Pharmaceutical and Biomedical Analysis
Volume105
DOIs
Publication statusPublished - Feb 5 2015

Fingerprint

Capillary electrophoresis
Cyclodextrins
Capillary Electrophoresis
Isomers
Stereoisomerism
Enantiomers
Electrolytes
Analgesics
Buffers
tapentadol
Impurities
Derivatives

Keywords

  • Capillary electrophoresis
  • Chiral separation
  • Cyclodextrin
  • Migration order
  • Nucynta
  • Tapentadol

ASJC Scopus subject areas

  • Analytical Chemistry
  • Drug Discovery
  • Pharmaceutical Science
  • Spectroscopy
  • Clinical Biochemistry

Cite this

Enantiomeric separation of tapentadol by capillary electrophoresis-Study of chiral selectivity manipulation by various types of cyclodextrins. / Znaleziona, Joanna; Fejos, Ida; Ševčík, Juraj; Douša, Michal; Béni, S.; Maier, Vítězslav.

In: Journal of Pharmaceutical and Biomedical Analysis, Vol. 105, 05.02.2015, p. 10-16.

Research output: Contribution to journalArticle

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