Tytuł artykułu
Autorzy
Wybrane pełne teksty z tego czasopisma
Identyfikatory
Warianty tytułu
Języki publikacji
Abstrakty
Ketorolac (Ket) is a potent non-narcotic analgesic drug (among the nonsteroidal anti-inflammatory drugs). The physiological activity of Ket resides with (S)-(-)-Ket while the drug is marketed and administered as a racemic mixture. Therefore, it is desirable that the pharmacokinetics is measured and quantified for enantiomers individually and not as a total drug. The present paper is focused on relevant literature on LC enantioseparation of (RS)-Ket along with bioassay, pharmacokinetic and clinical studiem within the discipline of analytical chemistry. HPLC and Thin layer chromatography (TLC) methods using both direct and indirect approaches are discussed. The methods provide chirality recognition even in the absence of pure enantiomers. Besides, a brief discussion on resolution by crystallization and enzymatic methods is included. The most interesting aspects include establishment of structure and molecular asymmetry of diastereomeric derivatives using LC-MS, proton nuclear magnetic resonance spectrometry, and by drawing conformations in three dimensional views by using certain software. A brief discussion has also been provided on the recovery of native enantiomers by TLC.
Czasopismo
Rocznik
Tom
Strony
220--236
Opis fizyczny
Bibliogr. 75 poz., rys., wykr.
Twórcy
autor
- Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, 247667, India
Bibliografia
- 1. Fischer, J.; Ganellin, C. R. Analogue-based Drug Discovery; Wiley-VCH Verlag GmbH: Weinheim, 2006; p 521.
- 2. Macario, A.; Lipman, A. G. Pain Med. 2001, 2, 336–51.
- 3. https://www.drugs.com, Medication Guide approved by the U.S. FDA, 01 Sep 2020.
- 4. Mroszczak, E.; Combs, D.; Chaplin, M.; Tsina, I.; Tarnowski, T.; Rocha, C.; Tam, Y.; Boyd, A.; Young, J.; Depass, L. J. Clin. Pharmacol. 1996, 36, 521–39.
- 5. Handley, D. A.; Cervoni, P.; McCray, J. E.; McCullough, J. R. J. Clin. Pharmacol. 1998, 38(2S), 25S–35S; https://doi.org/10.1002/j.1552-4604.1998.tb04414.x.
- 6. Mroszczak, E. J.; Lee, F. W.; Combs, D.; Sarnquist, F. H.; Huang, B. L.; Wu, A. T.; Tokes, L. G.; Maddox, M. L.; Cho, D. K. Drug Metab. Dispos. 1987, 15, 618–26.
- 7. Harrington, P. J.; Khatri, H. N.; Schloemer, G. C. Preparation of Ketorolac. US Patent 6197976 B1, (Syntex USA LLC) dated 06 Mar 2001.
- 8. Baran, P. S.; Richter, J. M.; Lin, D. W. Angew. Chem. Int. Ed. 2005, 44, 609–12.
- 9. Sasaki, I.; Yamasaki, N.; Kasai, Y.; Imagawa, H.; Yamamoto, H. Tetrahedron Lett. 2020, 61, 151564.
- 10. Bhushan, R.; Martens, J. Amino Acids, Chromatographic Separation and Enantioresolution; HNB Publishing: New York, 2010.
- 11. Dixit, S.; Bhushan, R. Chromatographic analysis of chiral drugs. In TLC in Drug Analysis; Komsta, L., Waksmundzka-Hajnos, M., Sherma, J., Eds. Taylor and Francis: Boca Raton, 2014; pp 97–130.
- 12. Sethi, S.; Martens, J.; Bhushan, R. Biomed. Chromatogr. 2021, 35, e4990.
- 13. Malik, P.; Bhushan, R. ACS Org. Process. Res. Dev. 2018, 22, 789–95.
- 14. Batra, S.; Bhushan, R. Biomed. Chromatogr. 2017, 31, e3833.
- 15. Singh, M.; Sethi, S.; Bhushan, R. J. Sep. Sci. 2020, 43, 18–30.
- 16. Malik, P.; Bhushan, R. Biomed. Chromatogr. 2018, 32, e4217.
- 17. Diaz-Perez, M. J.; Chen, J. C.; Aubry, A. F.; Wainer, I. W. Chirality 1994, 6, 283–9.
- 18. Mroszczak, E. J.; Jung, D.; Yee, J.; Bynum, L.; Sevelius, H.; Massey, I. Pharmacotherapy 1990, 10(Pt2), 33S–9S.
- 19. Vakily, M.; Corrigan, B.; Jamali, F. Pharm. Res. 1995, 12, 1652–7.
- 20. Lynn, A. M.; Bradford, H.; Kantor, E. D.; Seng, K.-Y.; Salinger, D. H.; Chen, J.; Ellenbogen, R. G.; Vicini, P.; Anderson, G. D. Pediatr. Anesth. 2007, 104, 1040–51.
- 21. Lynn, A. M.; Bradford, H.; Kantor, E. D.; Andrew, M.; Vicini, P.; Anderson, G. D. Pediatr. Anesth. 2011, 21, 325–34.
- 22. Hermansson, J. J. Chromatogr. A. 1983, 269, 71–80.
- 23. Sztaricskai, F.; Neszmely, A.; Bognar, R. Tetrahedron Lett. 1980, 21, 2983–6.
- 24. Mills, M. H.; Mather, L. E.; Gu, X. S.; Huang, J. L. J. Chromatogr. B 1994, 658, 177–82.
- 25. Jones, D. J.; Bjorksten, A. R. J. Chromatogr. B 1994, 661, 165–7.
- 26. Tsina, I.; Tam, Y. L.; Boyd, A.; Rocha, C.; Massey, I.; Tarnowski, T. J. Pharm. Biomed. Anal. 1996, 15, 403–17.
- 27. Campanero, M. A.; Lopez-Ocariz, A.; Garcıa-Quetglas, E.; Sadaba, B.; Azanza, J. R. Chromatographia 1998, 48, 203–8.
- 28. Patri, S.; Patni, A. K.; Iyer, S. S.; Khuroo, A. H.; Monif, T.; Rana, S.; Kumar, S.; Jain, R. Chromatogr. Res. Int. 2011, Article ID 214793; https://doi.org/10.4061/2011/214793.
- 29. Ing-Lorenzini, K. R.; Desmeules, J.; Besson, M.; Veuthey, J-L.; Dayer, P.; Daali, Y. J. Chromatogr. A. 2009, 1216, 3851–6.
- 30. Kulo, A.; Mulabegovic, N.; Loga-Zec, S.; Allegaert, K.; de Hoon, J.; Verbesselt, R. Chromatographia 2014, 77, 803–12.
- 31. Dubey, S. K.; Hemanth, J.; Venkatesh, C.; Saha, R. N.; Pasha, S. J. Pharm. Anal. 2012, 2, 462–5.
- 32. Zheng, L.; Yang, J.; Guan, Y.; Zhang, L.; Song, C.; Zhang, X. Curr. Pharm. Anal. 2021, 17, 1 – 6 . https://doi.org/10.2174/1573412917999201110203024.
- 33. Kostiainen, R.; Kauppila, T. J. J. Chromatogr. A. 2009, 1216, 685–99.
- 34. Bakhtiar, R.; Ramos, L.; Tse, F. L. S. Chirality 2001, 13, 63–74.
- 35. Dossou, K. S. S.; Farcas, E.; Servais, A.-C.; Chiap, P.; Chankvetadze, B.; Crommen, J.; Fillet, M. J. Chromatogr. A. 2012, 1234, 56–63.
- 36. Mohammed, B. S.; Engelhardt, T.; Cameron, G. A.; Hawwa, A. F. Biopharm. Drug Dispos. 2013, 34, 377–86.
- 37. Maher, H. M.; Al-Taweel, S. M.; Alshehri, M. M.; Alzoman, N. Z. Chirality 2014, 26, 629–39.
- 38. Lal, M.; Bhushan, R. Biomed. Chromatogr. 2016, 30, 1526–34.
- 39. Dossou, K. S. S.; Chiap, P.; Chankvetadze, B.; Servais, A-C.; Fillet, M.; Crommen, J. J. Chromatogr. A. 2001, 1216, 7450–5.
- 40. Ye, Y. K.; Lord, B.; Stringham, R. W. J. Chromatogr. A. 2002, 945, 139–46.
- 41. Matarashvili, I.; Chankvetadze, L.; Tsintsadze, T.; Farkas, T.; Chankvetadze, B. Chromatographia 2015, 78, 473–9.
- 42. He, Y.; Wu, Y.; Cheng, L.; He, S.; Wang, Q.; Wang, H.; Ke, Y. Sep. Sci. Plus 2018, 01, 351–8. https://doi.org/10.1002/sscp.201800048.
- 43. Ikai, T.; Okamoto, Y. Chem. Rev. 2009, 109, 6077–101.
- 44. Ye, Y. K.; Lord, B.; Stringham, R. W. J. Chromatogr. A. 2002, 945, 139–46.
- 45. Ikai, T.; Yamamoto, C.; Kamigaito, M.; Okamoto, Y. Polym. J. 2006, 38, 91–108.
- 46. Matarashvili, I.; Ghughunishvili, D.; Chankvetadze, L.; Takaishvili, N.; Khatiashvili, T.; Tsintsadze, M.; Farkas, T.; Chankvetadze, B. J. Chromatogr. A. 2017, 1483, 86–92.
- 47. Yashima, E. J. Chromatogr. A. 2001, 906, 105–25.
- 48. Okamoto, Y.; Yashima, E. Angew. Chem. Int. Ed. 1998, 37, 1021–43.
- 49. Ismail, O. H.; Ciogli, A.; Villani, C.; Martino, M. D.; Pierini, M.; Cavazzini, A.; Bell, D. S.; Gasparrini, F. J. Chromatogr. A. 2016, 1427, 55–68.
- 50. Barhate, C. L.; Waha, M. F.; Breitbach, Z. S.; Bell, D. S.; Armstrong, D. W. Anal. Chim. Acta 2015, 898, 128–37. http://dx.doi.org/10.1016/j.aca.2015.09.048.
- 51. Starek, M.; Dabrowska, M.; Skucinski, J. Recent Patents Chem. Eng. 2010, 3, 49–73.
- 52. Del Bubba, M.; Checchini, L.; Lepri, L. Anal. Bioanal. Chem. 2013, 405, 533–54.
- 53. Sajewicz, M.; Kowalska, T. J. Planar Chromatogr. 2017, 30, 333–9.
- 54. Bhushan, R.; Martens, J. Biomed. Chromatogr. 1997, 11, 280–5.
- 55. Davankov, V. A. Ligand Exchange Chromatography; CRC Press: United Kingdom, 2018; p 218. e-book, ISBN: 9781351082471,1351082477.
- 56. Remelli, M. Curr. Med. Chem. 2017, 24, 818–28.
- 57. Malik, P.; Bhushan, R. J. Chromatogr. Sci. 2019, 57, 511–7.
- 58. Davankov, V. A. J. Chromatogr. A. 1994, 666, 55–76.
- 59. Singh, M.; Bhushan, R. J. Planar Chromatogr. 2019, 32, 475–9.
- 60. Bhushan, R.; Dixit, S. Biomed. Chromatogr. 2012, 26, 962–71.
- 61. Tanwar, S.; Bhushan, R. Chromatographia 2015, 78, 1113–34.
- 62. Bhushan, R.; Parshad, V. J. Chromatogr. A. 1996, 721, 369–72.
- 63. Dalgliesh, C. E. J. Chem. Soc. 1952, 137, 3940–2.
- 64. Martens, J.; Bhushan, R. Helvetica Chim. Acta 2014, 97, 161–87.
- 65. Srinivas, N. R. Biomed. Chromatogr. 2004, 18, 759–84.
- 66. Gusman, A.; Yuste, F.; Toscano, R. A.; Young, J. M. J. Med. Chem. 1986, 29, 589–91.
- 67. Hayball, P. J.; Tamblyn, J. G.; Holden, Y.; Wrobel, J. Chirality 1993, 5, 31–5.
- 68. Hayball, P. J.; Wrobel, J.; Tamblyn, J. G.; Nation, R. L. Br. J. Clin. Pharmac. 1994, 37, 75–8.
- 69. Malik, P.; Bhushan, R. New J. Chem. 2017, 41, 13681–91.
- 70. McL Mathieson, A. Acta Cryst. 1956, 9, 317.
- 71. Fulling, G.; Sih, C. J. J. Am. Chem. Soc. 1987, 109, 2845–8.
- 72. Kim, Y. H.; Cheong, C. S.; Lee, S. H.; Kim, K. S. Tetrahedron: Asymmetry 2001, 12, 1865–9.
- 73. Shinde, S. D.; Yadav, G. D. Process. Biochem. 2015, 50, 230–6.
- 74. Pérez-Venegas, M.; Rodríguez-Treviño, A. M.; Juaristi, E. ChemCatChem 2020, 12, 1782–8.
- 75. Friščić, T.; Trask, A. V.; Jones, W.; Motherwell, W. D. S. Angew. Chem.Int. Ed. 2006, 45, 7546–50; https://doi.org/10.1002/anie.200603235.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-85e7baa2-a03b-4801-993f-51efba1f1d48