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Portugaliae Electrochimica Acta
Print version ISSN 0872-1904
Port. Electrochim. Acta vol.26 no.5 Coimbra 2008
Study of Acid Catalyzed Reactions of Proton Pump Inhibitors at D.M.E.
Hanuman P. Gupta, Kalawati Saini,* Priyanka Dhingra and R. Pandey*
Department of Chemistry University of Rajasthan Jaipur, India
Received 26 October 2007; accepted 1 April 2008
Abstract
Acid catalyzed reactions of three proton pump inhibitors (PPIs), namely omeprazole, lansoprazole and pantoprazole, have been investigated and monitored by direct current polarography at dropping mercury electrode (D.M.E) in phosphate buffer (0.1 M) of pH 3-7.5. This gives well defined current-time profiles of individual electroactive degradation products along with their starting materials. The investigation shows that the order of stability of three PPIs can be written as: pantoprazole > omeprazole > lansoprazole. The rate of degradation of PPIs decreases with decreasing the basicity of the corresponding benzimidazole nitrogen of PPIs, as predicted by the effect of individual substituents on each of the benzimidazole rings. At pH 7.5 all three PPIs are almost stable and the observed half wave potentials (E1/2 ) are –1.07 V for omeprazole, –1.25 V for lansoprazole and –1.32 V for pantoprazole. On decreasing the pH from 7.5 to 3.0 the anodic shift in E1/2 values were observed along with degradation of the PPIs and simultaneous appearance of degradation products. The present study may provide an insight for designing more potent new proton pump inhibitors.
Keywords: polarography, stability, proton pump inhibitors (PPIs), half wave potential.
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References
1. (a) V. Figala, K. Klemm, B. Kohl, U. Kruger, G. Rainer, H. Schaefer, J. Senn-Bilfinger and E. Sturm, Chem. Commun. (1986) 125; (b) P. Lindberg, A Brandstrom, B. Wallmark, H. Mattsson, L. Rikner, J. Med. Res. 10 (1990) 1-54.
2. W.A. Simon, D.J. Keeling, S.M. Laing, C. Fallowfield and A.G. Taylor, Biochem. Pharmacol. 39 (1990) 1799. [ Links ]
3. M. Morii, H. Takata, H. Fujisaki and N. Takeguchi, Biochem. Pharmacol. 39 (1990) 661.
4. J. Senn-Bilfinger, U. Kruger, E. Sturm, V. Figala, K. Klemm, B. Kohl, G. Rainer, H. Schaefer, T.J. Blake, D.W. Darkin, R.J. Ife, C.A. Leach, R.C. Mitchell, E.S. Pepper, C.J. Salter, N.J. Viney, G. Huttner and L. Zsolnai, J. Org. Chem. 52 (1987) 4582.
5. A. Brandstrom, P. Lindberg, N.A. Bergman, T. Alminger, K. Ankner, U. Junggren, B. Lamm, P. Nordberg, M. Erickson, I. Grundevik, I. Hagin, K.-J. Hoffmann, S. Johansson, S. Larsson, I. Liifberg, K. Ohlson, B. Persson, I. Skinberg and L. Tekenbergs-Hjelte, Acta Chem. Stand. 43 (1989) 536.
6. G. Rackur, M. Bickel, H.-W. Fehlhaber, A. Herling, V. Hitzel, H.-J. Lang, M. Riisner and R. Weyer, Biochem. Biophys. Res. Commun. 128 (1985) 477.
7. A.S. Mee, J.L. Rowley, Aliment. Pharmacol. Ther. 10 (1996) 757-/763.
8. D. Jaspersen, K.L. Diehl, H. Schoeppner, P. Geyer, E.A. Martens, Aliment. Pharmacol. Ther. 12 (1998) 49-52.
9. H. Nagaya, H. Satoh, Y. Maki, Eur. J. Clin. Pharmacol. 45 (1993) 367-371.
10. S.K. Garg, Y. Chugh, S.K. Tripathi, N. Kumar, P.L. Sharma, Int. J. Clin. Pharmacol. Ther. 31 (1993) 96-99.
11. C.M. Spencer, D. Faulds, Indian Drugs 48 (1994) 404-430.
12. C.S.P. Sastry, Y.P. Naidu, S.S.N. Murty, Indian Drugs 33 (1996) 607-610.
13. C.S.P. Sastry, P.Y. Naidu, S.S.N. Murty, Talanta 44 (1997) 1211-1217.
14. A.M. Wahbi, O. Abdel-Razak, A.A. Gazy, H. Mahgoub, M.S. Moneeb, J. Pharm. Biomed. Anal. 30 (2002) 1133-1142.
15. N. Ozaltin, J. Pharm. Biomed. Anal. 20 (1999) 599-606.
16. N. Ozaltin, A. Kocer, J. Pharm. Biomed. Anal. 16 (1997) 337-342.
17. D. Dogrukol, Z. Tumalier, M. Tuncel, Pharmazie 53 (1998) 272-273.
18. S.N. Meyyanathan, J.R.A. Raj, B. Suresh, Indian Drugs 34 (1997) 403-406.
19. S. Ray, P. Kumar-De, Indian Drugs 31 (1994) 543-547.
20. N. Badwe, G.C. Kandpal, S.T. Hathiari, East Pharm. 39 (1996) 127-128.
21. M.A. Brooks, in: P.T. Kissinger, W.R. Heineman (Eds.), Laboratory Techniques in Electroanalytical Chemistry, 2nd Ed., Marcel Dekker, New York, 1996.
22. N. Ozaltin, A. Temizer, Electroanalysis 6 (1994) 799-803.
23. D. Dogrukol, M. Tuncel, Pharmazie 50 (1995) 701-702.
24. S. Pinzauti, P. Gratteri, S. Furlanetto, P. Mura, E. Dreassi, R. Phan-Tan-Luu, J. Pharm. Biomed. Anal. 14 (1996) 881-889.
25. H. Oelschlager, H. Knoth, Pharmazie 53 (1998) 242-244.
26. C. Yardimci, N. Ozaltin, Analyst 126 (2001) 361-366.
27. S. McClean, E. G’Kane, V.N. Ramachandran and W.F. Smyth, Analytica Chemica Acta 292 (1994) 81-89.
28. J.M. Shin, Y.M. Cho, G. Sachs, J. Am. Chem. Soc. 126 (2004) 7800–7811.
29. A.M. Qaisi, M.F. Tutunji, L.F. Tutunji, J. Pharm. Sci. 95 (2006) 384–391.
30. M.F. Tutunji, A.M. Qaisi, B.El-Eswed, L.F. Tutunji, J. Pharm. Sci. 323 (2006) 110-116.
*Corresponding author. E-mail address: kalawati.saini@gmail.com
* Corresponding author. E-mail address: kala.iitdchem@gmail.com