The Effect of Enantiomer Elution Order on the Determination of Minor Enantiomeric Impurity in Ketoprofen and Enantiomeric Purity Evaluation of Commercially Available Dexketoprofen Formulations

Molecules. 2020 Dec 11;25(24):5865. doi: 10.3390/molecules25245865.


In a recent study, opposite enantiomer elution order was observed for ketoprofen enantiomers on two amylose-phenylcarbamate-based chiral columns with the same chemical composition of the chiral selector but in one case with coated while in the other with an immobilized chiral selector. In the present study, the influence of this uncommon effect on method validation parameters for the determination of minor enantiomeric impurity in dexketoprofen was studied. The validated methods with two alternative elution orders for enantiomers were applied for the evaluation of enantiomeric impurity in six marketed dexketoprofen formulations from various vendors. In most of these formulations except one the content of enantiomeric impurity exceeded 0.1% (w/w).

Keywords: amylose tris(3-chloro-5-methylphenylcarbamate); dexketoprofen; enantiomer elution order reversal; enantiomeric impurity determination; method validation.

MeSH terms

  • Amylose / chemistry*
  • Calibration
  • Chemistry Techniques, Analytical
  • Chemistry, Pharmaceutical
  • Chromatography
  • Chromatography, High Pressure Liquid / methods*
  • Drug Compounding
  • Drug Contamination
  • Ketoprofen / analogs & derivatives*
  • Ketoprofen / chemistry
  • Limit of Detection
  • Phenylcarbamates / chemistry*
  • Reproducibility of Results
  • Stereoisomerism
  • Tromethamine / chemistry*


  • Phenylcarbamates
  • Tromethamine
  • Amylose
  • Ketoprofen
  • dexketoprofen trometamol