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Solution and Mixing Thermodynamics of Propranolol and Atenolol in Aqueous Media

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Abstract

Based on the van’t Hoff and Gibbs equations, the thermodynamic functions Gibbs energy, enthalpy, and entropy of dissolution, and of mixing of propranolol (PPN) and atenolol (ATN) in water at pH=11.5, were evaluated from solubility values determined at several temperatures. The equilibrium solubility values obtained for ATN were almost three hundred-fold higher than those for PPN. The enthalpies of dissolution were positive for both drugs, whereas the entropies of dissolution were both negative indicating a greater molecular organization after the drugs’ dissolution processes. Otherwise, the entropies of mixing were also negative in both cases indicating mixing-entropy is driving on drugs dissolution processes. The results were discussed in terms of solute-solvent interactions, especially hydrophobic hydration.

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References

  1. Hoffman, B.B., Lefkowitz, R.J.: In: Hardman, J.G., Limbird, L.E., Gilman, A.G. (eds.) Goodman & Gilman’s. The Pharmacological Basis of Therapeutics, 9th edn. McGraw-Hill, New York (1995)

    Google Scholar 

  2. Amidon, G.L., Lennernäs, H., Shah, V.P., Crison, J.R.: A theoretical basis for a biopharmaceutic drug classification: The correlation of in vitro drug product dissolution and in vivo bioavailability. Pharm. Res. 12, 413–420 (1995)

    Article  CAS  Google Scholar 

  3. Jiménez, J.A., Martinez, F.: Thermodynamic study of the solubility of acetaminophen in propylene glycol + water cosolvent mixtures. J. Braz. Chem. Soc. 17, 125–134 (2006)

    Article  Google Scholar 

  4. Betageri, G.V., Rogers, J.A.: Thermodynamics of partitioning of β-blockers in the n-octanol-buffer and liposome systems. Int. J. Pharm. 36, 165–173 (1987)

    Article  CAS  Google Scholar 

  5. Perlovich, G.L., Volkova, T.V., Bauer-Brandl, A.: Thermodynamic study of sublimation, solubility, solvation, and distribution processes of atenolol and pindolol. Mol. Pharm. 4, 929–935 (2007)

    Article  CAS  Google Scholar 

  6. Mora, C.P., Martínez, F.: Thermodynamic quantities relative to solution processes of naproxen in aqueous media at pH 1.2 and 7.4. Phys. Chem. Liq. 44, 585–596 (2006)

    Article  CAS  Google Scholar 

  7. Perlovich, G.L., Kurkov, S.V., Bauer-Brandl, A.: The difference between partitioning and distribution from a thermodynamic point of view: NSAIDs as an example. Eur. J. Pharm. Sci. 27, 150–157 (2006)

    Article  CAS  Google Scholar 

  8. US Pharmacopeia, 23rd edn. The United States Pharmacopeial Convention, Rockville (1994)

  9. The British Pharmacopoeia, vol. I. Her Majesty’s Stationery Office, London (1988)

  10. Budavari, S., O’Neil, M.J., Smith, A., Heckelman, P.E., Obenchain Jr., J.R., Gallipeau, J.A.R., D’Arecea, M.A.: The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals, 13th edn. Merck & Co. Inc., Whitehouse Station (2001)

    Google Scholar 

  11. Thomas, E., Rubino, J.: Solubility, melting point and salting-out relationships in a group of secondary amine hydrochloride salts. Int. J. Pharm. 130, 179–183 (1996)

    Article  CAS  Google Scholar 

  12. Martin, A., Bustamante, P., Chun, A.H.C.: Physical Pharmacy: Physical Chemical Principles in the Pharmaceutical Sciences, 4th edn. Lea & Febiger, Philadelphia (1993)

    Google Scholar 

  13. Stott, P.W., Williams, A.C., Barry, B.W.: Mechanistic study into the enhanced transdermal permeation of a model β-blocker, propranolol, by fatty acids: a melting point depression effect. Int. J. Pharm. 219, 161–176 (2001)

    Article  CAS  Google Scholar 

  14. Kristl, A., Vesnaver, G.: Thermodynamic investigation of the effect of octanol-water mutual miscibility on the partitioning and solubility of some guanine derivatives. J. Chem. Soc. Faraday Trans. 91, 995–998 (1995)

    Article  CAS  Google Scholar 

  15. Barton, A.: Handbook of Solubility Parameters and Other Cohesion Parameters, 2nd edn. CRC Press, New York (1991)

    Google Scholar 

  16. Krug, R.R., Hunter, W.G., Grieger, R.A.: Enthalpy-Entropy compensation. 2. Separation of the chemical from the statistical effect. J. Phys. Chem. 80, 2341–2351 (1976)

    Article  CAS  Google Scholar 

  17. Bustamante, P., Romero, S., Peña, A., Escalera, B., Reillo, A.: Nonlinear enthalpy-entropy compensation for the solubility of drugs in solvent mixtures: paracetamol, acetanilide and nalidixic acid in dioxane-water. J. Pharm. Sci. 87, 1590–1596 (1998)

    Article  CAS  Google Scholar 

  18. Bevington, P.R.: Data Reduction and Error Analysis for the Physical Sciences. McGraw-Hill, New York (1969)

    Google Scholar 

  19. Perlovich, G.L., Kurkov, S.V., Kinchin, A.N., Bauer-Brandl, A.: Thermodynamics of solutions. III: Comparison of the solvation of (+)-naproxen with other NSAIDs. Eur. J. Pharm. Biopharm. 57, 411–420 (2004)

    Article  CAS  Google Scholar 

  20. Pacheco, D.P., Manrique, Y.J., Martínez, F.: Thermodynamic study of the solubility of ibuprofen and naproxen in some ethanol + propylene glycol mixtures. Fluid Phase Equilib. 262, 23–31 (2007)

    Article  CAS  Google Scholar 

  21. Manrique, Y.J., Pacheco, D.P., Martínez, F.: Thermodynamics of mixing and solvation of ibuprofen and naproxen in propylene glycol + water cosolvent mixtures. J. Solution Chem. 37, 165–181 (2008)

    Article  CAS  Google Scholar 

  22. Tanford, C.: The Hydrophobic Effect: Formation of Micelles and Biological Membranes. Wiley, New York (1973)

    Google Scholar 

  23. Romero, S., Reillo, A., Escalera, B., Bustamante, P.: The behavior of paracetamol in mixtures of amphiprotic and amphiprotic-aprotic solvents: relationship of solubility curves to specific and nonspecific interactions. Chem. Pharm. Bull. 44, 1061–1064 (1996)

    CAS  Google Scholar 

  24. Zakeri-Milani, P., Valizadeh, H., Tajerzadeh, H., Azarmi, Y., Islambolchilar, Z., Barzegar, S., Barzegar-Jalali, M.: Predicting human intestinal permeability using single-pass intestinal perfusion in rat. J. Pharm. Pharmaceut. Sci. 10, 368–379 (2007)

    CAS  Google Scholar 

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Correspondence to Fleming Martínez.

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Triana, M.T., Reyes, A.C., Jimenez-Kairuz, A.F. et al. Solution and Mixing Thermodynamics of Propranolol and Atenolol in Aqueous Media. J Solution Chem 38, 73–81 (2009). https://doi.org/10.1007/s10953-008-9348-1

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  • DOI: https://doi.org/10.1007/s10953-008-9348-1

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