JOURNAL OF THE CZECH PHARMACEUTICAL SOCIETY AND THE SLOVAK PHARMACEUTICAL SOCIETY

Čes. slov. farm. 2006, 55(6):272-277

Potentiometric Determination of Aqueous Dissociation Constants of 2-,3-,4-{3-(4-Benzhydryl-piperazine-1-yl)-2-hydroxy-propoxy}-phenylcarbamic Acid Alkylesters, Water Insoluble Potential Blockers of ß-Adrenergic Receptors

A. Lišková, M. Blešová
Veterinární a farmaceutická univerzita Brno, Farmaceutická fakulta, Ústav chemických léčiv

Apparent ionization constants (w spKa) of potential drugs, a series of twelve protonated bases, 2-,3-,4-{3-(4-benzhydryl-piperazine-1-yl)-2-hydroxy-propoxy}-phenylcarbamic acid alkylesters dihydrochlorides, were determined by automated potentiometric titrations in mixtures water - methanol. Aqueous pKa were assessed by means of Yasuda-Shedlovsky equation. Approach for pKa determination was evaluated using trimecaine hydrochloride as the model compound. The first values of ionization constants ranged approximately from 2.7 to 3.2, the second ones from 6.5 to 7.2. Only a slight decrease in ionization constants with the number of carbon atoms was observed in homological series. Experimentally determined dissociation constants were compared with the values predicted by the computer program SPARC.

Keywords: dissociation constant; potentiometry; mixtures water, methanol; protonated bases

Received: June 8, 2006; Accepted: July 25, 2006; Published: June 1, 2006  Show citation

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Lišková A, Blešová M. Potentiometric Determination of Aqueous Dissociation Constants of 2-,3-,4-{3-(4-Benzhydryl-piperazine-1-yl)-2-hydroxy-propoxy}-phenylcarbamic Acid Alkylesters, Water Insoluble Potential Blockers of ß-Adrenergic Receptors. Čes. slov. farm. 2006;55(6):272-277.
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References

  1. Ishihama, Y., Nakamura, M., Miwa, T. et al.: J. Pharm. Sci. 2002; 91, 933-942. Go to original source... Go to PubMed...
  2. Cairns, D.: Essentials of Pharmaceutical Chemistry. 2 vyd. London, Pharmaceutical Press, 2003.
  3. Takács-Novák, K., Box, K. J., Avdeef, A.: Int. J. Pharm. 1997; 151, 235-248. Go to original source...
  4. Šůcha, L., Kotrlý, S.: Teoretické základy analytické chemie. Praha, SNTL, 1987.
  5. Bates, R. G.: Determination of pH: Theory and practice. 2. vyd. New York, John Wiley & Sons, 1973.
  6. IUPAC Compendium of Analytical Nomenclature. Definitive Rules 1997. 3. vyd. Oxford, Blackwell, 1998.
  7. DeLigny, C. L., Rehbach, M.: Rec. Trav. Chim. 1960; 79, 727-730. Go to original source...
  8. Bates, R. G., Paabo, M., Robinson, R. A.: J. Phys. Chem. 1963; 67, 1833-1838. Go to original source...
  9. Canals, I., Oumada, F. Z., Rosés, M., Bosch, E.: J. Chromatogr. A. 2001; 911, 191-202. Go to original source... Go to PubMed...
  10. Mizutani, M.: Z. Physik. Chem. 1925; 116, 350-358. Go to original source...
  11. Avdeef, A., Comer, J. E. A., Thomson, J. S.: Anal. Chem. 1993; 65, 42-49. Go to original source...
  12. Hawes, J. L., Kay, R. L.: J. Phys. Chem. 1965; 69, 24202431. Go to original source...
  13. Sarmini, K., Kenndler, E.: J. Biochem. Biophys. Methods 1999; 38, 123-137. Go to original source... Go to PubMed...
  14. Avdeef, A., Box, K. J., Comer, J. E. A. et al.: J. Pharm. Biomed. Anal. 1999; 20, 631-641. Go to original source... Go to PubMed...
  15. Opatřilová, R., Mokrý, P., Csöllei, J., Blešová, M.: Čes. slov. Farm. 2002; 51, 305-309.
  16. Český lékopis 2005. Praha, Grada Publishing 2005, s. 3129.
  17. Solntsev, K. M., Huppert, D., Agmon, N., Tolbert, L. M.: J. Phys. Chem. A 2000; 104, 4658-4669. Go to original source...
  18. Pešák M., Štolc S., Beneš, L.: Čes. slov. Farm. 1980; 29, 272-275.
  19. http://ibmlc2.chem.uga.edu/sparc/, 25.04.2006
  20. Karickhoff, S. W., McDaniel V. K., Melton, C. M. et al.: Environ. Toxicol. Chem. 1991; 10, 1405-1416. Go to original source...
  21. Hilal, S. H., Carreira, L. A., Melton C. M., Karickhoff, S. W.: Quant. Struct. Act. Relat. 1993; 12, 389-396. Go to original source...
  22. Hilal, S. H., Carreira, L. A., Melton C. M. et al.: J. Phys. Org. Chem. 1994; 7, 122-141. Go to original source...
  23. Hilal, S. H., Carreira, L. A., Karickhoff, S. W.: In: Quantitative Treatment of Solute/Solvent Interactions: Theoretical and Computational Chemistry (Polizer, P., Murray, J. S., ed.), Vol. 1, Amsterdam, Elsevier, 1994.
  24. Hilal, S. H., Carreira, L. A., Karickhoff, S. W.: Quant. Struct. Act. Relat. 1995; 14, 348-355. Go to original source...
  25. Perrin, D. D., Dempsey, B., Serjeant, E. P.: pKa Prediction for Organic Acids and Bases. London, Chapman and Hall, 1981. Go to original source...




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