Abstract
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).
Highlights
The difference in pharmacokinetic, pharmacodynamic, metabolic, and toxic properties between the enantiomers of chiral drugs and other biologically active compounds is well known [1,2,3]. On one side this fact and on the other, the rapid development of state-of-the-art technologies for the manufacturing [4,5,6,7,8] and analysis [8,9,10] of single enantiomers of chiral compounds enabled the commercialization of enantiomerically pure novel chiral drugs, as well as redevelopment of many well-known chiral drugs previously used as racemates in enantiomerically pure form [11,12,13]
The major goal of this study was to evaluate the effect of enantiomer elution order (EEO) on method validation parameters while keeping other factors minimal
Reported reversal of the EEO for ketoprofen on the Lux i-Amylose-3 column and its analogue with a coated chiral selector [1] was confirmed in the present study (Figure 2)
Summary
The difference in pharmacokinetic, pharmacodynamic, metabolic, and toxic properties between the enantiomers of chiral drugs and other biologically active compounds is well known [1,2,3].On one side this fact and on the other, the rapid development of state-of-the-art technologies for the manufacturing [4,5,6,7,8] and analysis [8,9,10] of single enantiomers of chiral compounds enabled the commercialization of enantiomerically pure novel chiral drugs, as well as redevelopment of many well-known chiral drugs previously used as racemates in enantiomerically pure form (so-called chiral switch) [11,12,13]. The difference in pharmacokinetic, pharmacodynamic, metabolic, and toxic properties between the enantiomers of chiral drugs and other biologically active compounds is well known [1,2,3]. Some chiral drugs are offered in both racemic as well as in enantiomerically pure formulations. The evaluation of enantiomeric purity of single-enantiomer chiral drug formulations is quite a hot topic nowadays. It has been considered for many years that eluting the minor impurity in front of the major component offers certain advantages for more precise quantification of the impurity [10,14,15,16,17]
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