Tapentadol enantiomers: Synthesis, physico-chemical characterization and cyclodextrin interactions

Journal of Pharmaceutical and Biomedical Analysis

Volumn 88, Issue , 2014, Pages 594-601

  Fejos, Ida ^a   He, Yang ^b   Völgyi, Gergely ^a   Kazsoki, Adrienn ^a   Sun, Jin ^b   Chen, Weiming ^b   Sohajda, Tamás ^c   Szente, Lajos ^c   Jiang, Xiangrui ^b   Béni, Szabolcs ^a  

^a SEMMELWEIS UNIVERSITY   (Hungary)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

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

Author keywords

Capillary electrophoresis; Chiral separation; Enantioselective synthesis; Migration order; Protonation constant

Indexed keywords

CYCLODEXTRIN; TAPENTADOL; TERTIARY AMINE;

AQUEOUS SOLUTION; ARTICLE; CAPILLARY ZONE ELECTROPHORESIS; ELECTROSPRAY; ENANTIOMER; ENANTIOSELECTIVITY; HUMAN; LIPOPHILICITY; METHYLATION; PARTITION COEFFICIENT; PH; PHYSICAL CHEMISTRY; POTENTIOMETRY; PRIORITY JOURNAL; PROTON TRANSPORT; SYNTHESIS;

CAPILLARY ELECTROPHORESIS; CHIRAL SEPARATION; ENANTIOSELECTIVE SYNTHESIS; MIGRATION ORDER; PROTONATION CONSTANT;

ALPHA-CYCLODEXTRINS; BETA-CYCLODEXTRINS; ELECTROPHORESIS, CAPILLARY; HYDROGEN-ION CONCENTRATION; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MORPHINE; PHENOLS; POTENTIOMETRY; PROTONS; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM; WATER;

EID: 84887399226     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2013.10.005     Document Type: Article

References (23)

1. Nightingale S. The neuropathic pain market. Nat. Rev. Drug Discov. 2012, 11:101-102.
2. Tzschentke T.M., Christoph T., Kögel B., Schiene K., Hennies H.H., Englberger W., Haurand M., Jahnel U., Cremers T.I.F.H., Friderichs E., De Vry J. (-)-(1R,2R)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol hydrochloride (tapentadol:HCl): a novel μ-opioid receptor agonist/norepinephrine reuptake inhibitor with broad-spectrum analgesic properties. J. Pharmacol. Exp. Ther. 2007, 323:265-276.
3. Avdeef A. Absorption and Drug Development: Solubility, Permeability and Charge State 2012, Wiley, New York. second ed.
4. Takács-Novák K. Physico-chemical Methods in Drug Discovery and Development 2012, IAPC Publishing, Zagreb.
5. Douša M., Lehnert P., Adamusová H., Bosáková Z. Fundamental study of enantioselective HPLC separation of tapentadol enantiomers using cellulose-based chiral stationary phase in normal phase mode. J. Pharm. Biomed. Anal. 2013, 74:111-116.
6. Deng X., De Cock B., Vervoort R., Pamperin D., Adams E., Van Schepdael A. Development of a validated capillary electrophoresis method for enantiomeric purity control and quality control of levocetirizine in a pharmaceutical formulation. Chirality 2012, 24:276-282.
7. Neumajer G., Sohajda T., Darcsi A., Toth G., Szente L., Noszal B., Beni S. Chiral recognition of dapoxetine enantiomers with methylated-gamma-cyclodextrin: a validated capillary electrophoresis method. J. Pharm. Biomed. Anal. 2012, 62:42-47.
8. Chankvetadze B. Enantioseparations by using capillary electrophoretic techniques: the story of 20 and a few more years. J. Chromatogr. A 2007, 1168:45-70.
9. Sohajda T., Varga E., Ivanyi R., Fejos I., Szente L., Noszal B., Beni 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.
10. Juvancz Z., Kendrovics R.B., Iványi R., Szente L. The role of cyclodextrins in chiral capillary electrophoresis. Electrophoresis 2008, 29:1701-1712.
11. Zhang Q., Li J.F., Tian G.H., Zhang R.X., Sun J., Suo J., Feng X., Fang D., Jiang X.R., Shen J.S. A practical and enantioselective synthesis of tapentadol. Tetrahedron: Asymmetry 2012, 23:577-582.
12. Avdeef A. Accurate measurements of the concentration of hydrogen ions with a glass electrode: Calibrations using the prideaux and other universal buffer solutions and a computer-controlled automatic titrator. Anal. Chem. 1978, 50:2137-2142.
13. Hwang T.L., Shaka A.J. Water suppression that works. Excitation sculpting using arbitrary wave-forms and pulsed-field gradients. J. Magn. Reson. Series A 1995, 112:275-279.
14. Kyvala M., Lukes I. OPIUM computer program. Chemometrics'95 1995, Book of abstracts 63.
15. Tam K.Y., Takács-Novák K. Multi-wavelength spectrophotometric determination of acid dissociation constants: a validation study. Anal. Chim. Acta 2001, 434:157-167.
16. Takács-Novák K., Avdeef A. Interlaboratory study of logP determination by shake-flask and potentiometric methods. J. Pharm. Biomed. Anal. 1996, 14:1405-1413.
17. Wallingford R.A., Ewing A.G. Capillary electrophoresis. Adv. Chromatogr. 1989, 29:1-76.
18. Mazák K., Noszál B. Lipophilicity of morphine microspecies and their contribution to the lipophilicity profile. Eur. J. Pharm. Sci. 2012, 45:205-210.
19. Santos M.A., Esteves M.A., Vaz M.C., Da Silva J.J.R., Noszal B., Farkas E. Microscopic acid-base equilibria of a synthetic hydroxamate siderophore analog, piperazine-1,4-bis(N-methylacetohydroxamic acid). J. Chem. Soc. Perkin Trans. Microsc. 1997, 2:1977-1983.
20. FDA Full Prescribing Information of Nucynta 2010.
21. Lomsadze K., Martínez-Girón A.B., Castro-Puyana M., Chankvetadze L., Crego A.L., Salgado A., Marina M.L., Chankvetadze B. About the role of enantioselective selector-selectand interactions and the mobilities of diastereomeric associates in enantiomer separations using CE. Electrophoresis 2009, 30:2803-2811.
22. Beni S., Sohajda T., Neumajer G., Ivanyi R., Szente L., Noszal 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.
23. Sohajda T., Szakacs Z., Szente L., Noszal B., Beni S. Chiral recognition of imperanene enantiomers by various cyclodextrins: a capillary electrophoresis and NMR spectroscopy study. Electrophoresis 2012, 33:1458-1464.