Separation and characterization of modified pregabalins in terms of cyclodextrin complexation, using capillary electrophoresis and nuclear magnetic resonance

Journal of Pharmaceutical and Biomedical Analysis

Volumn 51, Issue 4, 2010, Pages 842-852

  Béni, Szabolcs ^a   Sohajda, Tamás ^a   Neumajer, Gábor ^a   Iványi, Róbert ^b   Szente, Lajos ^b   Noszál, Béla ^a  

^a SEMMELWEIS UNIVERSITY   (Hungary)

^b CycloLab Cyclodextrin Research & Development Laboratory Ltd   (Hungary)

Author keywords

Capillary electrophoresis; Enantioseparation; Lyrica; NMR; Synthesis

Indexed keywords

6 MONODEOXY 6 MONO (3 HYDROXY)PROPYLAMINO BETA CYCLODEXTRIN; ANALGESIC AGENT; BUFFER; CYCLODEXTRIN DERIVATIVE; PREGABALIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CAPILLARY ZONE ELECTROPHORESIS; CHEMICAL MODIFICATION; CHROMATOPHORE; COMPLEX FORMATION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DERIVATIZATION; DISSOCIATION CONSTANT; ELECTRIC POTENTIAL; ENANTIOSELECTIVITY; ISOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PARTICLE SIZE; PH; PRIORITY JOURNAL; RACEMIC MIXTURE; SEPARATION TECHNIQUE; STOICHIOMETRY; TITRIMETRY;

ANALGESICS; CYCLODEXTRINS; DRUG CONTAMINATION; ELECTROPHORESIS, CAPILLARY; GAMMA-AMINOBUTYRIC ACID; HYDROGEN-ION CONCENTRATION; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; SILICON DIOXIDE; STEREOISOMERISM;

EID: 72149115408     PISSN: 07317085     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jpba.2009.10.010     Document Type: Article

References (24)

1. Scriba G.K.E. Pharmaceutical and biomedical applications of chiral capillary electrophoresis and capillary electrochromatography: an update. Electrophoresis 24 (2003) 2409-2421
2. Izake E.L. Chiral discrimination and enantioselective analysis of drugs: an overview. J. Pharm. Sci. 96 (2007) 1659-1676
3. Chankvetadze B. Enantioseparations by using capillary electrophoretic techniques. The story of 20 and a few more years. J. Chromatogr. A 1168 (2007) 45-70
4. Juvancz Z., Kendrovics R.B., Iványi R., and Szente L. The role of cyclodextrins in chiral capillary electrophoresis. Electrophoresis 29 (2008) 1701-1712
5. Szejtli J. Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 98 (1998) 1743-1753
6. Bryans J.S., and Wustrow D.J. 3-Substituted GABA analogs with central nervous system activity: a review. Med. Res. Rev. 19 (1999) 149-177
7. Freynhagen R., Strojek K., Griesing T., Whalen E., and Balkenohl M. Efficacy of pregabalin in neuropathic pain evaluated in a 12-week, randomised, double-blind, multicentre, placebo-controlled trial of flexible- and fixed-dose regimens. Pain 115 (2005) 254-263
8. Dworkin R.H., Corbin A.E., Young Jr. J.P., Sharma U., LaMoreaux L., Bockbrader H., Garofalo E.A., and Poole R.M. Pregabalin for the treatment of postherpetic neuralgia: a randomized, placebo-controlled trial. Neurology 60 (2003) 1274-1283
9. Crofford L.J., Rowbotham M.C., Mease P.J., Russell I.J., Dworkin R.H., Corbin A.E., Young Jr. J.P., LaMoreaux L.K., Martin S.A., and Sharma U. Pregabalin for the treatment of fibromyalgia syndrome. Results of a randomized, double-blind, placebo-controlled trial. Arth. Rheum 52 (2005) 1264-1273
10. Silverman R.B. From basic science to blockbuster drug: the discovery of Lyrica. Angew. Chem. Int. Ed. 47 (2008) 3500-3504
11. Mandal U., Sarkar A.K., Gowda K.V., Agarwal S., Bose A., Bhaumik U., Ghosh D., and Pal T.K. Determination of pregabalin in human plasma using LC-MS-MS. Chromatographia 67 (2008) 237-243
12. Berry D., and Millington C. Analysis of pregabalin at therapeutic concentrations in human plasma/serum by reversed-phase HPLC. Ther. Drug Monit. 27 (2005) 451-456
13. Vermeij T.A.C., and Edelbroek P.M. Simultaneous high-performance liquid chromatographic analysis of pregabalin, gabapentin and vigabatrin in human serum by precolumn derivatization with o-phtaldialdehyde and fluorescence detection. J. Chromatogr. B 810 (2004) 297-303
14. Lin S., Brower P.L., and Winkle D.D. Chiral HPLC separations for process development of S-(+)-isobutyl GABA, a potential anti-epileptic agent. J. Liq. Chromatogr. Relat. Technol. 19 (1996) 2699-2708
15. Zhang Y., Holliman C., Tang D., Fast D., and Michael S. Development and validation of a direct enantiomeric separation of pregabalin to support isolated perfused rat kidney studies. J. Chromatogr. B 875 (2008) 148-153
16. Jadhav A.S., Pathare D.B., and Shingare M.S. Validated enantioselective LC method, with precolumn derivatization with Marfey's reagent, for analysis of the antiepileptic drug pregabalin in bulk drug samples. Chromatographia 65 (2007) 253-256
17. Chen X., Zhang D., Deng J., and Fu X. Determination of optical impurity of pregabalin by HPLC with pre-column chiral derivatization. J. Chromatogr. Sci. 46 (2008) 42-44
18. Yoshinaga M., and Tanaka M. Use of selectively methylated β-cyclodextrin derivatives in chiral separation of dansylamino acids by capillary zone electrophoresis. J. Chromatogr. A 679 (1994) 359-365
19. Deng X., and Mani N.S. A facile, environmentally benign sulfonamide synthesis in water. Green Chem. 8 (2006) 835-838
20. Hoekstra M.S., Sobieray D.M., Schwindt M.A., Mulhern T.A., Grote T.M., Huckabee B.K., Hendrickson V.S., Franklin L.C., Granger E.J., and Karrick G.L. Chemical Development of CI-1008, an enantiomerically pure anticonvulsant. Org. Process Res. Dev. 1 (1997) 26-38
21. Wallingford R.A., and Ewing A.G. Capillary electrophoresis. Adv. Chromatogr. 29 (1989) 1-76
22. Rundlett K.L., and Armstrong D.W. Examination of the origin, variation, and proper use of expressions for the estimation of association constants by capillary electrophoresis. J. Chromatogr. A 721 (1996) 173-186
23. M. Kyvala, I. Lukes, OPIUM computer program, Chemometrics'95 Pardubice (1995) Book of abstracts 63. http://www.natur.cuni.cz/∼kyvala/opium.html.
24. Wren S.A.C., and Rowe R.C. Theoretical aspects of chiral separation in capillary electrophoresis. I. Initial evaluation of a model. J. Chromatogr. 603 (1992) 235-241