Chiral separation of five arylpropionic acid drugs and determination of their enantiomers in pharmaceutical preparations by reversed-phase high performance liquid chromatography with cellulose-tris- (4-methylbenzoate) stationary phase

doi:10.3724/SP.J.1123.2014.06026

Abstract

Abstract:

Chromatographic behaviors for enantiomeric separation of arylpropionic acid drugs were systematically developed by reversed phase-high performance liquid chromatography (RP-HPLC) using cellulose-tris-(4-methylbenzoate) (CTMB) as chiral stationary phase (CSP). The effects of the composition of the mobile phase, additives and temperature on chiral separation of flurbiprofen, pranoprofen, naproxen, ibuprofen and loxoprofen were further investigated. The enantiomers had been successfully separated on CSP of CTMB by the mobile phase of methanol-0.1%(v/v) formic acid except naproxen by acetonitrile-0.1%(v/v) formic acid at 25 ℃. The mechanisms of the racemic resolution for the above mentioned five drugs are discussed thermodynamically and structurally. The resolutions between respective enantiomers for arylpropionic acid drugs on CTMB had significant differences due to their chromatographic behaviors. The order of resolutions ranked pranoprofen, loxoprofen, flurbiprofen, ibuprofen and naproxen. The method established has been successfully applied to the determination of the enantiomers of the five drugs in commercial preparations under the optimized conditions. It proved that the method is simple, reliable and accurate.

Key words: arylpropionic acid drugs, cellulose-tris-(4-methylbenzoate), chiral separation, chiral stationary phase, reversed-phase high performance liquid chromatography (RP-HPLC)

CLC Number:

O658

LUO An, WAN Qiang, FAN Huajun, CHEN Zhi, WU Xuehao, HUANG Xiaowen, ZANG Linquan. Chiral separation of five arylpropionic acid drugs and determination of their enantiomers in pharmaceutical preparations by reversed-phase high performance liquid chromatography with cellulose-tris- (4-methylbenzoate) stationary phase[J]. Chinese Journal of Chromatography, 2014, 32(9): 1013-1018.

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