Enantioselective determination of chlorpheniramine in various formulations by HPLC using carboxymethyl-β-cyclodextrin as a chiral additive

Archives of Pharmacal Research

Volumn 31, Issue 4, 2008, Pages 523-529

  Chen, Quan Cheng ^a   Jeong, Su Jin ^a   Hwang, Gwi Seo ^b   Kim, Kyeong Ho ^c   Kang, Jong Seong ^a  

^a Chungnam National University   (South Korea)

^b Gachon University College of Medicine   (South Korea)

^c Kangwon National University   (South Korea)

Author keywords

Carboxymethyl cyclodextrin; Chiral selector; Chlorpheniramine; Enantioselective determination; Stability constant

Indexed keywords

BETA CYCLODEXTRIN DERIVATIVE; CARBOXYMETHYL BETA CYCLODEXTRIN; CARBOXYMETHYL-BETA-CYCLODEXTRIN; CHLORPHENIRAMINE; HISTAMINE H1 RECEPTOR ANTAGONIST;

ARTICLE; CALIBRATION; CHEMISTRY; DRUG DOSAGE FORM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION AND PURIFICATION; ISOMERISM; METHODOLOGY; PH; REPRODUCIBILITY; STANDARD;

BETA-CYCLODEXTRINS; CALIBRATION; CHLORPHENIRAMINE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DOSAGE FORMS; HISTAMINE H1 ANTAGONISTS; HYDROGEN-ION CONCENTRATION; ISOMERISM; REPRODUCIBILITY OF RESULTS;

EID: 43049115707     PISSN: 02536269     EISSN: 19763786     Source Type: Journal    
DOI: 10.1007/s12272-001-1188-3     Document Type: Article

References (29)

1. Agyei, N. M., Gahm, K. H., and Stalcup, A. M., Chiral separations using heparin and dextran sulfate in capillary zone electrophoresis. Anal. Chim. Acta, 307, 185-191 (1995).
2. Baumy, Ph., Morin, Ph., Dreux, M., Viaud, M. C., Boye, S., and Guillaumet, G., Determination of β-cyclodextrin inclusion complex constants for 3,4-dihtdro-2H-1-benzopyran enantiomers by capillary electrophoresis. J. Chromatogr. A, 707 311-326 (1995).
3. Bressolle, F., Audran, M., Pham, T. N., and Vallon, J. J., Cyclodextrins and enantiomeric separations of drugs by liquid chromatography and capillary electrophoresis: basic principles and new developments. J. Chromatogr. B, 687, 303-336 (1996).
4. 3H]-mepyramine. J. Pharmacol. Exp. Ther., 209, 437-442 (1979).
5. Chankvetadze, B., Burjanadze, N., Maynard, D. M., Bergander, K., Bergenthal, D., and Blaschke, G., Comparative enantioseparations with native β-cyclodextrin and heptakis-(2-O-methyl-3,6-di-O-sulfo)-β-cyclodextrin in capillary electrophoresis. Electrophoresis, 23, 3027-3034 (2002).
6. De Beer, J. O., Vandenbroucke, C. V., Massart, D. L., and De Spiegeleer, B. M., Half-fraction and full factorial designs versus central composite design for retention modelling in reversed-phase ion-pair liquid chromatography. J. Pharm. Biomed. Anal., 14, 525-541 (1996).
7. Fried, K. M., Young, A. E., Yasuda, S. U., and Wainer, I. W., The enantioselective determination of chlorpheniramine and its major metabolites in human plasma using chiral chromatography on a b-cyclodextrin chiral stationary phase and mass spectrometric detection. J. Pharm. Biomed. Anal., 27, 479-488 (2002).
8. Gottia, R., Cavrini, V., Andrisanoa, V., and Mascellani, G., Semisynthetic chondroitins as chiral buffer additives in capillary electrophoresis. J. Chromatogr. A, 845, 247-256 (1999).
9. Haginaka, J. and Kagawa, C., Retentivity and enantioselectivity of uniformly sized molecularly imprinted polymers for d-chlorpheniramine and l-chlorpheniramine in hydro-organic mobile phases. J. Chromatogr. B, 804, 19-24 (2004).
10. Haginaka, J. and Kagawa, C., Uniformly sized molecularly imprinted polymer for d-chlorpheniramine: Evaluation of retention and molecular recognition properties in an aqueous mobile phase. J. Chromatogr. A, 948, 77-84 (2002).
11. Haginaka, J., Kagawa, C., and Matsunaga, H., Separation of enantiomers on a chiral stationary phase based on ovoglycoprotein. VII. Comparison of chiral recognition ability of ovoglycoprotein from chicken and Japanese quail egg whites. J. Chromatogr. A, 858, 155-165 (1999).
12. Haginaka, J. and Kanasugi, N., Separation of basic drug enantiomers by capillary zone electrophoresis using ovoglycoprotein as a chiral selector. J. Chromatogr. A, 782, 281-288 (1997).
13. Hiep, B. T., Khanh, V., Hung, N. K., Thuillier, A., and Gimenez, F., Determination of the enantiomers of chlorpheniramine and its main monodesmethyl metabolite in urine using achiral-chiral liquid chromatography. J. Chromatogr. B, 707, 235-240 (1998).
14. Jin, L. J. and Li, S. F. Y., Comparison of chiral recognition capabilities of cyclodextrins for the separation of basic drugs in capillary zone electrophoresis. J. Chromatogr. B Biomed. Sci. Appl., 708, 257-266 (1998).
15. Koch, K. M., O'Connor-Semmes, R. L., Davis, I. M., and Yin, Y., Stereoselective pharmacokinetics of chlorpheniramine and the effect of ranitidine. J. Pharm. Sci., 87, 1097-1100(1998).
16. 1-acid glycoprotein column. J. Chromatogr. A, 818, 43-52 (1998).
17. Matsunaga, H., Tanimoto, T., and Haginaka, J., Separation of basic drug enantiomers by capillary electrophoresis using methylated glucuronyl glucosyl β-cyclodextrin as a chiral selector. J. Sep. Sci., 25, 1175-1182 (2002).
18. Olmo, B., García, A., Marín, A., and Barbas, C., New approaches with two cyano columns to the separation of acetaminophen, phenylephrine, chlorpheniramine and related compounds. J. Chromatogr. B, 817, 159-165 (2005).
19. Sakurai, E., Yamasaki, S., Iizuka, Y., Hikichi, N., and Niwa, H., The optical resolution of racemic chlorpheniramine and its stereoselective pharmacokinetics in rat plasma. J. Pharm. Pharmacol., 44, 44-47 (1992).
20. Scott R. L., Some comments on the Benesi-Hildebrand equation. Rec. Trav. Chim., 75, 787-789 (1956).
21. Stalcup, A. M. and Gahm, K. H., Applications of sulfated cyclodextrins to chiral separations by capillary zone electrophoresis. Anal. Chem., 68, 1360-1368 (1996).
22. Sun, S. W. and Lin, Y. R., Optimization of capillary electrophoretic separation of chlorpheniramine enantiomers by a Plackett-Burman design. Determination of enantiomeric purity of dexchlorpheniramine. J. Liq. Chromatogr. Rel. Tech., 24, 2051-2066 (2001).
23. 3H]- mepyramine. Proc. Natl. Acad. Sci., 75, 6290-6294 (1978).
24. Van Eeckhaut, A., Detaevernier, M. R., and Michotte, Y., Development of a validated capillary electrophoresis method for enantiomeric purity testing of dexchlorpheniramine maleate. J. Chromatogr. A, 958, 291-297 (2002).
25. Wind, M., Hoffmann, P., Wagner, H., and Thormann, W., Chiral capillary electrophoresis as predictor for separation of drug enantiomers in continuous flow zone electrophoresis. J. Chromatogr. A, 895, 51-65 (2000).
26. Wu, H. L., Huang, C. H., Chen, S. H., and Wu, S. M., Chiral quantitation of pheniramine chlorpheniramine and brompheniramine maleates by capillary zone electrophoresis. J. Chromatogr. Sci., 37, 24 (1999).
27. Xu, H., Yu, X., and Chen, H., Enantiomeric separation of basic drugs with partially filled serum albumin as chiral selector in capillary electrophoresis. Anal. Sci., 20, 1409-1413 (2004).
28. Yasuda, S. U., Zannikos, P., Young, A. E., Fried, K. M., Wainer, I. W., and Woosley, R. L., The roles of CYP2D6 and stereoselectivity in the clinical pharmacokinetics of chlorpheniramine maleate. Br. J. Clin. Pharmacol., 53, 519-525 (2002).
29. Yuan, L., Liu, J., Yan, Z., Ai, P., Meng, X., and Xu, Z., Enantioseparation of chlorpheniramine by high speed countercurrent chromatography using carboxymethyl-β-cyclodextrin as chiral selector. J. Liq. Chromatogr. Rel. Tech., 28, 3057-3063 (2005).