Enantioselective determination of modafinil in pharmaceutical formulations by capillary electrophoresis, and computational calculation of their inclusion complexes

Microchimica Acta

Volumn 166, Issue 3-4, 2009, Pages 311-317

  ALAzzam, Khaldun M ^a   Saad, Bahruddin ^a   Adnan, Rohana ^a   Saleh, Muhammad Idiris ^a  

^a SCHOOL OF PHYSICS   (Malaysia)

Author keywords

Capillary electrophoresis; Computational calculations; Enantiomers; Modafinil; Pharmaceutical formulations; Wake promoting agent

Indexed keywords

EID: 70449520077     PISSN: 00263672     EISSN: 14365073     Source Type: Journal    
DOI: 10.1007/s00604-009-0209-4     Document Type: Article

References (22)

1. Cass QB, Galatti TF (2008) 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 46:937-944.
2. Mitchell HA, Bogenpohl JW, Liles LC, Epstein MP, Bozyczko-Coyne D, Williams M, Weinshenker D (2008) Behavioral responses of dopamine β-hydroxylase knockout mice to modafinil suggest a dual noradrenergic-dopaminergic mechanism of action. Pharmacol Biochem Behav 91:217-222.
3. Prisinzano T, Podobinski J, Tidgewell K, Luo M, Swenson D (2004) Synthesis and determination of the absolute configuration of the enantiomers of modafinil. Tetrahedron Asymmetr 15:1053-1058.
4. Wong YN, King SP, Simcoe D, Gorman S, Laughton W, McCormick GC, Grebow P (1999) Open-label, single-dose pharmacokinetic study of modafinil tablets: influence of age and gender in normal subjects. J Clin Pharmacol 39:281-288.
5. Roth T, White D, Schmidt-Nowara W, Wesnes KA, Niebleq G, Arora S, Black J (2006) Effect of armodafinil in the treatment of residual excessive sleepiness associated with obstructive sleep apnea/hypopnea syndrome: A 12-week, multicenter, double-blind, randomized, placebo-controlled study in Ncpap-adherent adults. Clin Ther 28:689-706.
6. Gorman SH (1999) Determination of the d- and l- enantiomers of modafinil in human plasma utilizing liquid-liquid extraction and high-performance liquid chromatography. J Chromatogr B 730:1-7.
7. Cass QB, Kohn CK, Calafatti SA, Aboul-Enein HY (2001) An enantioselective assay for (±)-modafinil. J Pharm Biomed Anal 26:123-130.
8. Donovan JL, Malcolm RJ, Markowitz JS, DeVane CL (2003) Chiral analysis of d- and l- modafinil in human serum: application to human pharmacokinetic studies. Ther Drug Monit 25:197-202.
9. Elbashir AA, Suliman FEO, Saad B, Aboul-Enein HY (2009) Determination of aminoglutethimide enntiomers in pharmaceutical formulations by capillary electrophoresis using methylated-β-cyclodextrin as a chiral selector and computational calculation for their respective inclusion complexes. Talanta 77:1388-1393.
10. Pang N, Zhang Z, Bai Y, Liu H (2009) A study of the interaction between enantiomers of zolmitriptan and hydroxypropyl-beta-cyclodextrin by capillary electrophoresis. Anal Bioanal Chem 393:313-320.
11. ICH-Q2A guideline for industry: Text on validation of analytical procedures March 1995.
12. In Y, Tomoo K, Ishida T, Sakamoto Y (2004) Crystal and molecular structure of an (S)-(+)-enantiomer of modafinil, a novel wake-promoting agent. Chem Pharm Bull 52:1186-1189.
13. Steiner T, Koellner G (1994) Crystalline β-cyclodextrin hydrate at various humidities: fast, continuous, and reversible dehydration studied by x-ray diffraction. J Am Chem Soc 116:5122-5128.
14. Ma S, Shen S, Haddad N, Tang W, Wang J, Lee H, Yee N, Senanayake C, Grinberg N (2009) Chromatographic and spectroscopic studies on the chiral recognition of sulfated β-cyclodextrin as chiral mobile phase additive enantiomeric separation of a chiral amine. J Chromatogr A 1216:1232-1240.
15. Yan C, Li X, Xiu Z, Hao C (2006) A quantum-mechanical study on the complexation of β-cyclodextrin with quercetin. J Mol Struct (Theochem) 764:95-100.
16. Subramanian G (2007) Chiral Separation Techniques. Wiley, Weinheim, Germany.
17. Cao Y, Xiao X, Ji S, Lu R, Guo Q (2004) Study of the inclusion processes of styrene and α-methyl-styrene in β-cyclodextrin. Spectrochim Acta Part A 60:815-820.
18. Bednarek E, Bocian W, Michalska K (2008) NMR and molecular modeling study, as complementary techniques to capillary electrophoresis method to elucidate the separation mechanism of linezolid enantiomers. J Chromatogr A 1193:164-171.
19. Aree T, Chaichit N (2002) Crystal structure of β-cyclodextrin-dimethylsulfoxide inclusion complex. Carbhydr Res 337:2487.
20. Yan C, Xiu Z, Li X, Hao C (2007) Molecular modeling study of β-cyclodextrin complexes with (+)-catechin and (-)-epicatechin. J Mol Graphics Modell 26:420-428.
21. Lipkowitz KB, Stoehr CM (1996) Detailed experimental and theoretical analysis of chiral discrimination: enantioselective binding of R/S methyl mandelate by β-cyclodextrin. Chirality 8:341-350.
22. Bednarek E, Bocuan W, Michalska K (2008) NMR and molecular modeling study, as complementary techniques to capillary electrophoresis method to elucidate the separation mechanism of linezolid enantiomers. J Chromatogr A 1193:164-171.