Chiral Separation of Ketoprofen Racemate by using Chirex<sup>®</sup> 3005 and Kromasil<sup>®</sup> CHI-II Chiral Column

Tae Ho Yoon; In Ho Kim

Korean Journal of Chemical Engineering, Vol.21, No.2, 521-526, March, 2004

DOI10.1007/BF02705443 Export Citation

Chiral Separation of Ketoprofen Racemate by using Chirex^® 3005 and Kromasil^® CHI-II Chiral Column

Tae Ho Yoon, and In Ho Kim^†

Department of Chemical Engineering, Chungnam National University, Daejeon 305-764, Korea

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Ketoprofen is a non-steroid anti-inflammatory drug (NSAID) that has analgesic, anti-inflammatory and antipyretic properties, of which pharmacological activity has been contributed mainly by the S-ketoprofen enantiomer. To gain highly purified S-ketoprofen enantiomer from ketoprofen racemate, suitable stationary phase was investigated by comparing R-type naphthylglycine and 3,5-dinitrobenzoic acid of Chirex^® 3005 and O,O'-bis(4-tertbutyl-benzoyl)-N and N'-diallyl-L-tartardiamide of Kromasil^® CHI-II. S-ketoprofen enantiomer was successfully isolated by using the Kromasil column as well as the mobile phase of hexane/tert-butyl methyl ether/acetic acid (v/v)=60/40/0.1. Equilibrium constants of R- and S-ketoprofen were obtained by pulsed injection method (PIM) at various concentrations of ketoprofen racemate and loading sample amounts, which serve the basic information on overloading sample volume and amounts. A volume of 100 μl containing 3.0 mg of ketoprofen racemate to Kromasil column (250 mm×4.6 mm) resulted in 85% recovery of injected sample under an high concentration (30 mg/ml) feed condition.

Keywords:Ketoprofen Racemate;HPLC;Chiral Separation;Enantiomer;Fractionation

[References]

Blanco M, Coello J, Iturriaga H, Maspoch S, Perez-Maseda C, J. Chromatogr. A, 793(1), 165 (1998)
Boisvert J, Caille G, McGilveray IJ, Qureshi SA, J. Chromatogr. B, 690, 189 (1997)
Gindy AE, Ashour A, Abdel-Fattah L, Shababa MM, J. Pharm. Biomed. Anal., 25(2), 171 (2001)
Francotte ER, Richert P, J. Chromatogr. A, 769(1), 101 (1997)
Grubb NG, Rudy DW, Hall SD, J. Chromatogr. B, 678(2), 237 (1996)
Jagota NK, Stewart JT, J. Chromatogr. A, 604(2), 255 (1992)
Kakodkar SV, Witiak DT, Johnson TP, Baldwin JR, Rahwan RG, J. Medicinal Chem., 22(1), 77 (1979)
Menzel-Soglowek S, Geisslinger G, Brune K, J. Chromatogr. B, 532, 295 (1990)
Meyring M, Chankvetadze B, Blaschke G, J. Chromatogr. A, 876, 157 (2000)
Morrison RT, Boyd RN, "Organic Chemistry," 6th ed., 136, Prentice-Hall Inc., New York, U.S.A. (1992)
Oshima T, Inoue K, Furusaki S, Goto M, J. Membr. Sci., 217(1-2), 87 (2003)
Pietta P, Manera E, Ceva P, J. Chromatogr., 387, 525 (1987)
Sallustio BC, Abas AP, Hayball J, Purdie YJ, Meffin PJ, J. Chromatogr. B, 374(2), 329 (1986)
Schurig V, Juza M, J. Chromatogr. A, 757, 119 (1997)
Wainer IW, "Drug Streochemistry: Analytical Method and Pharmacology," 2nd ed., Marcel Dekker, New York, 67 (1993)
Wright MR, Jamali F, J. Chromatogr. B, 616, 59 (1993)
Van Overbeke A, Baeyens W, VanDen Bossche W, Dewaele C, J. Pharm. Biomed. Anal., 12(7), 911 (1994)

[Referenced By]

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[1] Blanco M, Coello J, Iturriaga H, Maspoch S, Perez-Maseda C, J. Chromatogr. A, 793(1), 165 (1998)

[2] Boisvert J, Caille G, McGilveray IJ, Qureshi SA, J. Chromatogr. B, 690, 189 (1997)

[3] Gindy AE, Ashour A, Abdel-Fattah L, Shababa MM, J. Pharm. Biomed. Anal., 25(2), 171 (2001)

[4] Francotte ER, Richert P, J. Chromatogr. A, 769(1), 101 (1997)

[5] Grubb NG, Rudy DW, Hall SD, J. Chromatogr. B, 678(2), 237 (1996)

[6] Jagota NK, Stewart JT, J. Chromatogr. A, 604(2), 255 (1992)

[7] Kakodkar SV, Witiak DT, Johnson TP, Baldwin JR, Rahwan RG, J. Medicinal Chem., 22(1), 77 (1979)

[8] Menzel-Soglowek S, Geisslinger G, Brune K, J. Chromatogr. B, 532, 295 (1990)

[9] Meyring M, Chankvetadze B, Blaschke G, J. Chromatogr. A, 876, 157 (2000)

[10] Morrison RT, Boyd RN, "Organic Chemistry," 6th ed., 136, Prentice-Hall Inc., New York, U.S.A. (1992)

[11] Oshima T, Inoue K, Furusaki S, Goto M, J. Membr. Sci., 217(1-2), 87 (2003)

[12] Pietta P, Manera E, Ceva P, J. Chromatogr., 387, 525 (1987)

[13] Sallustio BC, Abas AP, Hayball J, Purdie YJ, Meffin PJ, J. Chromatogr. B, 374(2), 329 (1986)

[14] Schurig V, Juza M, J. Chromatogr. A, 757, 119 (1997)

[15] Wainer IW, "Drug Streochemistry: Analytical Method and Pharmacology," 2nd ed., Marcel Dekker, New York, 67 (1993)

[16] Wright MR, Jamali F, J. Chromatogr. B, 616, 59 (1993)

[17] Van Overbeke A, Baeyens W, VanDen Bossche W, Dewaele C, J. Pharm. Biomed. Anal., 12(7), 911 (1994)