Enantiomeric separation and determination of the enantiomeric impurity of armodafinil by capillary electrophoresis with sulfobutyl ether-β- cyclodextrin as chiral selector

Molecules

Volumn 17, Issue 1, 2012, Pages 303-314

  Wang, Wei ^a   Xiang, Suyun ^b   Zhou, Xiaojuan ^a   Ji, Yibing ^a   Xiang, Bingren ^a  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

^b NANJING NORMAL UNIVERSITY   (China)

Author keywords

Armodafinil; Capillary electrophoresis; Enantiomeric impurity; Sulfobutyl ether cyclodextrin

Indexed keywords

BENZHYDRYL DERIVATIVE; BETA CYCLODEXTRIN DERIVATIVE; CENTRAL STIMULANT AGENT; METHANOL; MODAFINIL; SBE4 BETA CYCLODEXTRIN; SBE4-BETA-CYCLODEXTRIN; SOLVENT;

ARTICLE; CAPILLARY ELECTROPHORESIS; CHEMISTRY; ISOLATION AND PURIFICATION; LIMIT OF DETECTION; PH; REPRODUCIBILITY; SIGNAL NOISE RATIO; STANDARD; STEREOISOMERISM;

BENZHYDRYL COMPOUNDS; BETA-CYCLODEXTRINS; CENTRAL NERVOUS SYSTEM STIMULANTS; ELECTROPHORESIS, CAPILLARY; HYDROGEN-ION CONCENTRATION; LIMIT OF DETECTION; METHANOL; REFERENCE STANDARDS; REPRODUCIBILITY OF RESULTS; SIGNAL-TO-NOISE RATIO; SOLVENTS; STEREOISOMERISM;

EID: 84862966364     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17010303     Document Type: Article

References (30)

1. Czeisler, C.A.; Walsh, J.K.; Roth, T.; Hughes, R.J.; Wright, K.P.; Kingsbury, L.; Arora, S.; Schwartz, J.R.L.; Niebler, G.E.; Dinges, D.F. Modafinil for excessive sleepiness associated with shift-work sleep disorder. N. Engl. J. Med. 2005, 353, 476-486. (Pubitemid 41127292)
2. Erman, M.K.; Rosenberg, R. For the US modafinil shift work sleep disorder study group. Modafinil for excessive sleepiness associated with chronic shift work sleep disorder: Effects on patient functioning and health-related quality of life. Prim. Care Companion J. Clin. Psychiatry 2007, 9, 188-194. (Pubitemid 46878737)
3. Gerrard, P.; Malcolm, R. Mechanisms of modafinil: A review of current research. Neuropsychiatr. Dis. Treat. 2007, 3, 349-364. (Pubitemid 47215010)
4. Hou, R.H.; Langle, R.W.; Szabadi, E.; Bradshaw, C.M. Comparison of diphenhydramine and modafinil on arousal and autonomic functions in healthy volunteers. J. Psychopharmacol. (Oxford) 2007, 21, 567-578. (Pubitemid 47472721)
5. Myrick, H.; Malcolm, R.; Taylor, B.; LaRowe, S. Modafinil: Preclinical, clinical, and postmarketing surveillance-A review of abuse liability issues. Ann. Clin. Psychiatry 2004, 16, 101-109. (Pubitemid 39089110)
6. Roth, T.; White, D.; Schmidt-Nowara, W.; Wesnes, K.A.; Niebler, G.; Arora, S.; Black, J. Effects of armodafinil in the treatment of residual excessive sleepiness associated with obstructive sleep apnea/hypopnea syndrome: A 12-week, multicenter, double-blind, randomized, placebocontrolled study in nCPAP-Adherent adults. Clin. Ther. 2006, 28, 689-706. (Pubitemid 44067263)
7. Wong, Y.N.; King, S.P.; Simcoe, D.; Gorman, S.; Laughton, W.; McCormick, G.G.; Gerbow, P. Open label, single dose pharmacokinetic study of modafinil tablets: Influence of age and gender in normal subjects. J. Clin. Pharmacol. 1999, 39, 281-288. (Pubitemid 29148551)
8. Dinges, D.F.; Arora, S.; Darwish, M.; Niebler, G.E. Pharmacodynamic effects on alertness of single doses of armodafinil in healthy subjects during a nocturnal period of acute sleep loss. Curr. Med. Res. Opin. 2006, 22, 159-167. (Pubitemid 43106919)
9. Nishino, S.; Okuro, M. Armodafinil for excessive daytime sleepiness. Drugs Today 2008, 44, 395-414.
10. Lankford, D.A. Armodafinil: A new treatment for excessive sleepiness. Expert Opin. Investig. Drugs 2008, 17, 565-573. (Pubitemid 351578173)
11. Cephalon. Pipeline. Available online: Http://www.cephalon.com/our- science/pipeline/ (accessed on 21 January 2008).
12. ICH Expert Working Group. Specifications: Test procedures and acceptance criteria for new drug substances and new drug products: Chemical substances. Q6A. Current Step 4 version. In International Conference on Harmonization of Technical Requirements for the Registration of Pharmaceutical Human Use, London, UK, 6 October 1999; Available online: Http://www.ich.org/fileadmin/Public-Web- Site/ICH-Products/Guidelines/Quality/Q6A/Step4/Q6 Astep4.pdf (accessed on 6 June 2011).
13. Gorman, S.H. Determination of the D- and L-enantiomers of modafinil in human plasma utilizing liquid-liquid extraction and high-performance liquid chromatography. J. Chromatogr. B Biomed. Sci. Appl. 1999, 730, 1-7. (Pubitemid 29290600)
14. Donovan, J.L.; Malcolm, R.J.; Markowitz, J.S.; DeVane, C.L. Chiral analysis of d- and L-modafinil in human serum: Application to human pharmacokinetic studies. Ther. Drug Monit. 2003, 25, 197-202. (Pubitemid 36373427)
15. Cass, Q.B.; Galatti, T.F. A method for determination of the plasma levels of modafinil enantiomers, (±)-modafinic acid and modafinil sulphone by direct human plasma injection and bidimensional achiral-chiral chromatography. J. Pharm. Biomed. Anal. 2008, 46, 937-944. (Pubitemid 351410491)
16. Rao, R.N.; Shinde, D.D. Enantioselective separation and determination of adrafinil and modafinil on Chiralcel OJ-H column in rat serum and urine using solid-phase extraction followed by HPLC. Biomed. Chromatogr. 2009, 23, 811-816.
17. AL Azzam, K.M.; Saad, B.; Adnan, R.; Saleh, M.I. Enantioselective determination of modafinil in pharmaceutical formulations by capillary electrophoresis, and computational calculation of their inclusion complexes. Microchim. Acta 2009, 166, 311-317.
18. Béni, S.; Sohajda, T.; Neumajer, G.; Iványi, R.; Szente, L.; Noszál, B. Separation and characterization of modified pregabalins in terms of cyclodextrin complexation, using capillary electrophoresis and nuclear magnetic resonance. J. Pharm. Biomed. Anal. 2010, 51, 842-852.
19. Sohajda, T.; Varga, E.; Iványi, R.; Fejos, I.; Szente, L.; Noszál, B.; Béni, S. Separation of vinca alkaloid enantiomers by capillary electrophoresis applying cyclodextrin derivatives and characterization of cyclodextrin complexes by nuclear magnetic resonance spectroscopy. J. Pharm. Biomed. Anal. 2010, 53, 1258-1266.
20. Lipka, E.; Vaccher, M.; Vaccher, C.; Bonte, J. Chiral Capillary Electrophoresis with Highly Sulfated Cyclodextrins; Resolution of Benzoxazolinone Aminoalcohols, and Aminoketon Precursors, Potential Adrenergic Ligands. Anal. Lett. 2010, 43, 2356-2371.
21. Kuo, C.Y.; Liao, K.S.; Liu, Y.C.; Yang, W.B. Bis-indole derivatives for polysaccharide compositional analysis and chiral resolution of d-,l-monosaccharides by ligand exchange capillary electrophoresis using borate-cyclodextrin as a chiral selector. Molecules 2011, 16, 1682-1694.
22. Castro-Puyana, M.; Lomsadze, K.; LCrego, A.; Marina, M.L.; Chankvetadze, B. Separation of enantiomers of deprenyl with various CDs in CE and the effect of enantiomer migration order on enantiomeric impurity determination of selegiline in active ingredients and tablets. Electrophoresis 2007, 28, 388-394.
23. Dung, P.T.; Ko, M.Y.; Choi, H.J.; Sin, K.S.; Kim, K.H. Determination of enantiomeric impurity of etodolac by capillary electrophoresis using (2-hydroxypropyl)-beta-cyclodextrin. Arch. Pharm. Res. 2008, 31, 1218-1223.
24. Michalska, K.; Pajchel, G.; Tyski, S. Determination of enantiomeric impurity of linezolid by capillary electrophoresis using heptakis-(2,3-diacetyl- 6-sulfato)-beta-cyclodextrin. J. Chromatogr. A 2008, 1180, 179-186.
25. Sánchez-Hernández, L.; García-Ruiz, C.; Crego, A.L.; Marina, M.L. Sensitive determination of D-carnitine as enantiomeric impurity of levo-carnitine in pharmaceutical formulations by capillary electrophoresis- tandem mass spectrometry. J. Pharm. Biomed. Anal. 2010, 53, 1217-1223.
26. Deng, X.; Hai, X.; Vervoort, R.; Pamperin, D.; Adams, E.; van Schepdael, A. Development and validation of a chiral capillary electrophoresis method for assay and enantiomeric purity control of pramipexole. J. Sep. Sci. 2011, 34, 3070-3076.
27. Zhou, L.; Thompson, R.; Reamer, R.A.; Miller, C.; Welch, C.; Ellison, D.K.; Wyvratt, J.M. Mechanistic study of enantiomeric recognition with native ?-cyclodextrin by capillary electrophoresis, reversed-phase liquid chromatography, nuclear magnetic resonance spectroscopy, electrospray mass spectrometry and circular dichroism techniques. J. Chromatogr. A 2003, 987, 409-420. (Pubitemid 36140117)
28. Chankvetadze, B.; Lindner, W.; Scriba, G.K. Enantiomer separations in capillary electrophoresis in the case of equal binding constants of the enantiomers with a chiral selector: Commentary on the feasibility of the concept. Anal. Chem. 2004, 76, 4256-4260. (Pubitemid 38943708)
29. Voskuhl, J.; Schaepe, K.; Ravoo, B.J. Enhanced chiral recognition by cyclodextrin dimers. Int. J. Mol. Sci. 2011, 12, 4637-4646.
30. Shi, J.H.; Ding, Z.J.; Hu, Y. Theoretical study on chiral recognition mechanism of methyl mandelate enantiomers on permethylated β-cyclodextrin. J. Mol. Model. 2011, doi:10.1007/s00894-011-1118-0.