Citation: 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. doi: 10.3724/SP.J.1123.2014.06026 shu

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

1.
College of Pharmacy, Guangdong Pharmaceutical University, Guangzhou 510006, China

Corresponding author: FAN Huajun,
Received Date: 17 June 2014
Available Online: 14 July 2014
Fund Project: 国家“重大新药创制”科技重大专项(2011ZX09102-001-31) (2011ZX09102-001-31)广东药学院师资队伍建设基金项目(52104109). (52104109)

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.
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沈阳化工大学材料科学与工程学院沈阳 110142