The European Physical Journal Special Topics

, Volume 226, Issue 5, pp 913–929

Solubility of pharmaceuticals: A comparison between SciPharma, a PC-SAFT-based approach, and NRTL-SAC

  • Baptiste Bouillot
  • Theodora Spyriouni
  • Sébastien Teychené
  • Béatrice Biscans
Review
Part of the following topical collections:
  1. Phase Equilibria and Their Applications

Abstract

The solubility of seven pharmaceutical compounds (paracetamol, benzoic acid, 4-aminobenzoic acid, salicylic acid, ibuprofen, naproxen and temazepam) in pure and mixed solvents as a function of temperature is calculated with SciPharma, a semi-empirical approach based on PC-SAFT, and the NRTL-SAC model. To conduct a fair comparison between the approaches, the parameters of the compounds were regressed against the same solubility data, chosen to account for hydrophilic, polar and hydrophobic interactions. Only these solubility data were used by both models for predicting solubility in other pure and mixed solvents for which experimental data were available for comparison. A total of 386 pure solvent data points were used for the comparison comprising one or more temperatures per solvent. SciPharma is found to be more accurate than NRTL-SAC on the pure solvent data used especially in the description of the temperature dependence. This is due to the appropriate parameterization of the pharmaceuticals and the temperature-dependent description of the activity coefficient in PC-SAFT. The solubility in mixed solvents is predicted satisfactorily with SciPharma. NRTL-SAC tends to overestimate the solubility in aqueous solutions of alcohols or shows invariable solubility with composition in other cases.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Supplementary material

References

  1. 1.
    H. Renon, J.M. Prausnitz, AIChE J. 14, 135 (1968)CrossRefGoogle Scholar
  2. 2.
    T.C. Frank, J.R. Downey, S.K. Gupta, Chem. Eng. Prog. 95, 41 (1999)Google Scholar
  3. 3.
    C.-C. Chen, Y. Song, Ind. Eng. Chem. Res. 43, 8354 (2004)CrossRefGoogle Scholar
  4. 4.
    F. Ruether, G. Sadowski, J. Pharm. Sci. 98, 4205 (2009)CrossRefGoogle Scholar
  5. 5.
    I. Tsivintzelis, I.G. Economou, G.M. Kontogeorgis, AIChE J. 55, 756 (2009)CrossRefGoogle Scholar
  6. 6.
    A. Klamt, J. Phys. Chem. 99, 2224 (1995)CrossRefGoogle Scholar
  7. 7.
    A. Klamt, F. Eckert, M. Hornig, E.M. Beck, T. Burger, J. Comput. Chem. 23, 275 (2002)CrossRefGoogle Scholar
  8. 8.
    S. Gracin, T. Brinck, A. Rasmuson, Ind. Eng. Chem. Res. 41, 5114 (2002)CrossRefGoogle Scholar
  9. 9.
    I. Hahnenkamp, G. Graubner, J. Gmehling, Int. J. Pharm. 388, 73 (2010)CrossRefGoogle Scholar
  10. 10.
    U. Weidlich, J. Gmehling, Ind. Eng. Chem. Res. 26, 1372 (1987)CrossRefGoogle Scholar
  11. 11.
    B. Bouillot, S. Teychené, B. Biscans, Ind. Eng. Chem. Res. 52, 9276 (2013)CrossRefGoogle Scholar
  12. 12.
    B. Bouillot, S. Teychené, B. Biscans, Ind. Eng. Chem. Res. 52, 9285 (2013)CrossRefGoogle Scholar
  13. 13.
    E. Mullins, Y.A. Liu, A. Ghaderi, S. Fast, Ind. Eng. Chem. Res. 47, 1707 (2008)CrossRefGoogle Scholar
  14. 14.
    H. Tung, J. Tabora, N. Variankaval, D. Bakken, C. Chen, J. Pharm. Sci. 97, 1813 (2008)CrossRefGoogle Scholar
  15. 15.
    F.L. Mota, A.P. Carneiro, S.P. Pinho, E.A. Macedo, Eur. J. Pharm. Sci. 37, 499 (2009)CrossRefGoogle Scholar
  16. 16.
    E. Sheikholeslamzadeh, S. Rohani, Ind. Eng. Chem. Res. 51, 464 (2012)CrossRefGoogle Scholar
  17. 17.
    B. Bouillot, S. Teychené, B. Biscans, Fluid Phase Equilib. 309, 36 (2011)CrossRefGoogle Scholar
  18. 18.
    T. Spyriouni, X. Krokidis, I.G. Economou, Fluid Phase Equilib. 302, 331 (2011)CrossRefGoogle Scholar
  19. 19.
    J.M. Prausnitz, R.N. Lichtenthaler, E. Gomes de Azevedo, Molecular Thermodynamics of Fluid-Phase Equilibria (Prentice Hall, 1999)Google Scholar
  20. 20.
    J. Gross, G. Sadowski, Ind. Eng. Chem. Res. 40, 1244 (2001)CrossRefGoogle Scholar
  21. 21.
    C.-C. Chen, Fluid Phase Equilib. 83, 301 (1993)CrossRefGoogle Scholar
  22. 22.
    A. Fredenslund, R.L. Jones, J.M. Prausnitz, AIChE J. 21, 1086 (1975)CrossRefGoogle Scholar
  23. 23.
    C.-C. Chen, P.A. Crafts, Ind. Eng. Chem. Res. 45, 4816 (2006)CrossRefGoogle Scholar
  24. 24.
    F. Tumakaka, J. Gross, G. Sadowski, Fluid Phase Equilib. 228, 89 (2005)CrossRefGoogle Scholar
  25. 25.
    J. Gross, G. Sadowski, Ind. Eng. Chem. Res. 41, 5510 (2002)CrossRefGoogle Scholar
  26. 26.
    R.A. Granberg, A.C. Rasmuson, J. Chem. Eng. Data 44, 1391 (1999)CrossRefGoogle Scholar
  27. 27.
    J. Barra, F. Lescure, E. Doelker, P. Bustamante, J. Pharm. Pharmacol. 49, 644 (1997)CrossRefGoogle Scholar
  28. 28.
    G.L. Perlovich, T.V. Volkova, A. Bauer-Brandl, J. Pharm. Sci. 95, 2158 (2006)CrossRefGoogle Scholar
  29. 29.
    A. Beerbower, P.L. Wu, A. Martin, J. Pharm. Sci. 73, 179 (1984)CrossRefGoogle Scholar
  30. 30.
    F.A. Restaino, A.N. Martin, J. Pharm. Sci. 53, 636 (1964)CrossRefGoogle Scholar
  31. 31.
    B. Long, J. Li, R. Zhang, L. Wan, Fluid Phase Equilib. 297, 113 (2010)CrossRefGoogle Scholar
  32. 32.
    J. Barra, M.A. Pena, P. Bustamante, Eur. J. Pharm. Sci. 10, 153 (2000)CrossRefGoogle Scholar
  33. 33.
    A. Shalmashi, A. Eliassi, J. Chem. Eng. Data 53, 199 (2008)CrossRefGoogle Scholar
  34. 34.
    F.L. Nordstrom, A.C. Rasmuson, J. Chem. Eng. Data 51, 1668 (2006)CrossRefGoogle Scholar
  35. 35.
    H. Matsuda, K. Kaburagi, S. Matsumoto, K. Kurihara, K. Tochigi, K. Tomono, J. Chem. Eng. Data 54, 480 (2009)CrossRefGoogle Scholar
  36. 36.
    S. Gracin, A.C. Rasmuson, J. Chem. Eng. Data 47, 1379 (2002)CrossRefGoogle Scholar
  37. 37.
    D.M. Stovall, C. Givens, S. Keown, K.R. Hoover, E. Rodriguez, W.E. Jr. Acree, M.H. Abraham, Phys. Chem. Liq. 43, 261 (2005)CrossRefGoogle Scholar
  38. 38.
    P. Bustamante, M.A. Pena, J. Barra, J. Pharm. Pharmacol. 50, 975 (1998)CrossRefGoogle Scholar
  39. 39.
    C.R. Daniels, A.K. Charlton, R.M. Wold, E. Pustejovsky, A.N. Furman, A.C. Bilbrey, J.N. Love, J.A. Garza, W.E. Jr. Acree, M.H. Abraham, Phys. Chem. Liq. 42, 481 (2004)CrossRefGoogle Scholar
  40. 40.
    P.J. Richardson, D.F. McCafferty, A.D. Woolfson, Int. J. Pharm. 78, 189 (1992)CrossRefGoogle Scholar
  41. 41.
    A. Jouyban, Handbook of Solubility Data for Pharmaceuticals (CRC Press, Boca Raton, 2009)Google Scholar
  42. 42.
    J. Marrero, J. Abildskov, Solubility and Related Properties of Large Complex Chemicals, Part 2 (DECHEMA Frankfurt, 2005)Google Scholar
  43. 43.
    P. Bustamante, S. Romero, A. Reillo, Pharm. Pharmacol. Commun. 1, 505 (1995)Google Scholar
  44. 44.
    D.P. Pacheco, F. Martinez, Phys. Chem. Liq. 45, 581 (2007)CrossRefGoogle Scholar
  45. 45.
    H. Hojjati, S. Rohani, Org. Process Res. Dev. 10, 1101 (2006)CrossRefGoogle Scholar
  46. 46.
    M.A.A. Fakhree, S. Ahmadian, V. Panahi-Azar, W.E. Jr. Acree, A. Jouyban, J. Chem. Eng. Data 57, 3303 (2012)CrossRefGoogle Scholar
  47. 47.
    M.A. Pena, P. Bustamante, B. Escalera, A. Reillo, J. Pharm. Biomed. Anal. 36, 571 (2004)CrossRefGoogle Scholar

Copyright information

© EDP Sciences and Springer 2017

Authors and Affiliations

  • Baptiste Bouillot
    • 1
  • Theodora Spyriouni
    • 2
  • Sébastien Teychené
    • 3
  • Béatrice Biscans
    • 3
  1. 1.École Nationale Supérieure des Mines SPIN-EMSE, CNRS: UMR5307, LFGSaint-EtienneFrance
  2. 2.Scienomics SARL, 17 square Edouard VIIParisFrance
  3. 3.Université de Toulouse, CNRS: UMR5503, LGCToulouse Cedex 4France

Personalised recommendations