Development and validation of a new high performance liquid chromatographic method for enantioseparation of dorzolamide hydrochloride on a coated cellulose phenylcarbamate chiral stationary phase

Journal of Liquid Chromatography and Related Technologies

Volumn 34, Issue 14, 2011, Pages 1367-1380

  Shamsipur, Mojtaba ^a   Abdollahpour, Assem ^b   Heydari, Rouhollah ^a  

^a RAZI UNIVERSITY   (Iran)

^b TARBIAT MODARES UNIVERSITY   (Iran)

Author keywords

cellulose phenylcarbamate chiral stationary phase; dorzolamide hydrochloride; enantiomers; enantioseparation; high performance liquid chromatography; validation

Indexed keywords

2-PROPANOL; CHIRAL STATIONARY PHASE; DIETHYLAMINES; DORZOLAMIDE; ENANTIOSEPARATIONS; LIMITS OF DETECTION; MOBILE PHASE; N-HEXANE; NEW HIGH; ORGANIC COMPONENTS; RELATIVE STANDARD DEVIATIONS; SENSITIVE METHOD; VALIDATION;

CELLULOSE; CHIRALITY; CHROMATOGRAPHIC ANALYSIS; CHROMATOGRAPHY; ENANTIOMERS; ENANTIOSELECTIVITY; FLOW RATE; HEXANE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIQUIDS;

PHASE SEPARATION;

2 PROPANOL; CARBAMIC ACID DERIVATIVE; CELLULOSE; DIETHYLAMINE; DORZOLAMIDE; HEXANE; PHENYLCARBAMATE; UNCLASSIFIED DRUG;

ARTICLE; CHIRAL CHROMATOGRAPHY; ENANTIOMER; ENANTIOSELECTIVITY; FLOW RATE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIMIT OF DETECTION; LIMIT OF QUANTITATION; SENSITIVITY ANALYSIS; TEMPERATURE SENSITIVITY;

EID: 80052330887     PISSN: 10826076     EISSN: 1520572X     Source Type: Journal    
DOI: 10.1080/10826076.2011.570843     Document Type: Article

References (30)

1. Jenner, P.; Testa, B. The Influence of Stereochemical Factors on Drug Disposition. Drug Metab. Rev. 1973, 2, 117-184.
2. Ariens, E. J. Stereochemistry, a Basis for Sophisticated Nonsense in Pharmaceutics and Clinical Pharmacology. Eur. J. Clin. Pharmac. 1984, l26, 663-668.
3. Aboul-Enein, H. Y.; Wainer, I. W. The Impact of Stereochemistry on Development and Use. Chem. Anal. 1997, 142, 403-419.
4. U.S. Food and Drug Administration. Strongly Urges Companies to Evaluate Racemates and Enantiomers for New Drugs, Chirality 1992, 4, 338-340.
5. Borras, J.; Scozzafava, A.; Menabuoni, L.; Mincione, F.; Briganti, F.; Mincione, G.; Supuran, C. T. Carbonic Anhydrase Inhibitors: Synthesis of Water-Soluble, Topically Effective Intraocular Pressure Lowering Aromatic/Heterocyclic Sulfonamides Containing 8-Quinoline-sulfonyl Moieties: Is the Tail More Important than the Ring?, Bioorg. Med. Chem. 1999, 7, 2397-2406.
6. Reynolds, J. E. F. Martindale, the Extra Pharmacopoeia, 32nd ed; The Pharmaceutical Press: London, 1999.
7. Material Safety Data Sheet, USP, Catalog number 1225292, 2006.
8. USP 30, NF 25, United States Pharmacopoeia, vol. 2; United States Pharmacopoeial Convention Inc.: Rockville, MD, USA: 2007. p 1990.
9. B'Hymer, C.; Montes-Bayon, M.; Caruso, J. A. Marfey's Reagent: Past, Present, and Future Uses of 1-Fluoro-2,4-dinitrophenyl-5-L-alanine Amide. J. Sep. Sci. 2003, 26, 7-19.
10. Matuszewski, B. K.; Constanzer, M. L. Indirect Chiral Separation and Analyses in Human Biological Fluids of the Stereoisomers of a Thienothiopyran-2-sulfonamide (TRUSOPT), a Novel Carbonic Anhydrase Inhibitor with Two Chiral Centers in the Molecule. Chirality 1992, 4, 515-519.
11. Matuszewski, B. K.; Constanzer, M. L.; Kiganda, M. Analytical Chiral Separation of the Stereoisomers of a Novel Carbonic Anhydrase Inhibitor and its Deethylated Metabolite, and the Assignment of Absolute Configuration of the Human Metabolite and Chiral Degradation Products. Pharmaceu. Res. 1994, 11, 449-454.
12. Dovletoglou, A.; Thomas, S. M.; Berwick, L., Ellison, D. K., Tway, P. C. Development of Practical HPLC Methods for Analysis and Quality Assessment of the Novel Carbonic Anhydrase Inhibitor MK-0507 and the Acetamidosulfonamide Intermediate. J. Liq. Chromatogr. Rel. Technol. 1995, 18, 2337-2352.
13. Novak, T. J.; Berwick, L. Determination of the Enantiomeric Composition of a Novel Topically Active Carbonic Anhydrase Inhibitor by HPLC. J. Liq. Chromatogr. Rel. Technol. 1998, 21, 1883-1896.
14. Shamsipur, M.; Heydari, R.; Jamasbi, E. S.; Abdollahpour, A. Chiral Separation and Quantitation of Dorzolamide Hydrochloride Enantiomers by High Performance Liquid Chromatography. J. Sep. Sci. 2010, 33, 2328-2333.
15. Chankvetadze, B.; Yamamoto, C.; Kamigaito, M.; Tanaka, N.; Nakanishi, K.; Okamoto, Y. High-Performance Liquid Chromatographic Enantioseparations on Capillary Columns Containing Monolithic Silica Modified with Amylose Tris(3,5-Dimethylphenylcarbamate). J. Chromatogr. A 2006, 11, 46-52.
16. Ikai, T.; Okamoto, Y. Structure Control of Polysaccharide Derivatives for Efficient Separation of Enantiomers by Chromatography. Chem. Rev. 2009, 109, 6077-6101.
17. Okamoto, Y.; Kawashima, M.; Hatada, K. Chromatographic Resolution. XI. Controlled Chiral Recognition of Cellulose Triphenylcarbamate Derivatives Supported on Silica Gel. J. Chromatogr. 1986, 363, 173-186.
18. Zhang, T.; Nguyen, D.; Franco, P.; Murakami, T.; Ohnishi, A.; Kurosawa H. Cellulose 3,5-Ddimethylphenylcarbamate Immobilized on Silica. A New Chiral Stationary Phase for the Analysis of Enantiomers, Anal. Chim. Acta 2006, 557, 221-228.
19. Chen, X. M.; Liu, Y. Q.; Qin, F.; Kong, L.; Zou, H. F. Synthesis of Covalently Bonded Cellulose Derivative Chiral Stationary Phases with a Bifunctional Reagent of 3-(Triethoxysilyl) Propyl Isocyanate. J. Chromatogr. A 2003, 1010, 185-194.
20. Chen, X. M..; Qin, F.; Liu, Y. Q.; Huang, X. D.; Zou, H. F. Synthesis of Chiral Stationary Phases with Radical Polymerization Reaction of Cellulose Phenylcarbamate Derivatives and Vinylized Silica Gel. J. Chromatogr. A 2004, 1034, 109-116.
21. Ghanem, A.; Hoenen, H.; Aboul-Enein, H. Y. Application and Comparison of Immobilized and Coated Amylase Tris-(3,5-Dimethylphenylcarbamate) Stationary Phases for the Enantioselective Separation of β-Blockers Enantiomers by Liquid Chromatography. Talanta 2006, 68, 602-609.
22. Ali, I., Aboul-Enein, H. Y. Immobilized Polysaccharide CSPs: An Advancement in Enantiomeric Separations. Current Pharmaceut. Anal. 2007, 3, 71-82.
23. Mey, R.; Paulus, H.; Lamparter, E.; Blaschke, G. Enantioseparation of Amfepramone (rac-Diethylpropion): Preparative Separation of the Enantiomers and Enantioselective Analysis. Chirality 1999, 11, 772-780.
24. Wang, X.; Li, W. Z.; Zhao, Q. Y.; Li, Y. M.; Chen, L. R. Normal-Phase HPLC Enantioseparation of Novel Chiral Metal Tetrahedrane-Type Clusters on an Amylose-Based Chiral Stationary Phase. Anal. Sci. 2005, 21, 125-128.
25. Grieb, S. J.; Matlin, S. A.; Belenguer, A. M.; Ritchie, H. J. Chiral High Performance Liquid Chromatography with Cellulose Carbamates Coated Phases. Influence of Support Surface Chemistry on Enantioselectivity. J. Chromatogr. 1995, 697, 271-278.
26. Aboul-Enein, H. Y.; Ali, I. Comparison of the Chiral Resolution of Econazole, Miconazole, and Sulconazole by HPLC Using Normal-Phase Amylose CSPs. J. Anal. Chem. 2001, 370, 951-955.
27. Aboul-Enein, H. Y.; Ali, I. Enantiomeric Resolution of Some Substituted Tetralone Derivatives on Amylose Tris-(3,5-dimethyl phenylcarbamate) Chiral Stationary Phase in Reversed Phase Mode. J. Sep. Sci. 2001, 24, 831-834.
28. Schurig, V. Separation of Enantiomers by Gas Chromatography. J. Chromatogr. A 2001, 906, 275-299.
29. Ermer, J. Validation in Pharmaceutical Analysis. Part I: An Integrated Approach. J. Pharm. Biomed. Anal. 2001, 24, 755-767.
30. Shabir, G. A. Validation of High-Performance Liquid Chromatography Methods for Pharmaceutical Analysis Understanding the Differences and Similarities between Validation Requirements of the US Food and Drug Administration, the US Pharmacopeia and the International Conference on Harmonization. J. Chromatogr. A 2003, 987, 57-66.