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Employing Abraham and Hansen Parameters for Solubility Prediction of Ketoconazole in Binary Solvents at Various Temperatures

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Abstract

The Jouyban–Acree model is reported to be the most accurate mathematical model for predicting drug solubility in the mixed solvents at various temperatures. In this study, the solubility of ketoconazole is predicted using the Jouyban–Acree based general models in some previously reported co-solvency systems. For this purpose, parameters of the Hansen solubility and the Abraham solvation parameters are combined with the Jouyban–Acree model and are trained with reported solubility data for ketoconazole to reach predictive co-solvency models. For investigation of the models’ accuracies, the values for mean relative deviations of predicted data from published experimental values are calculated and discussed.

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References

  1. Clarysse, S., Psachoulias, D., Brouwers, J., Tack, J., Annaert, P., Duchateau, G., Reppas, C., Augustijns, P.: Postprandial changes in solubilizing capacity of human intestinal fluids for BCS class II drugs. Pharm. Res. 26, 1456–1466 (2009)

    Article  CAS  PubMed  Google Scholar 

  2. Di, L., Fish, P.V., Mano, T.: Bridging solubility between drug discovery and development. Drug Discov. Today 17, 486–495 (2012)

    Article  CAS  PubMed  Google Scholar 

  3. Khan, A.D., Singh, L.: Various techniques of bioavailability enhancement: a review. J. Drug Deliv. Ther. 6, 34–41 (2016)

    Google Scholar 

  4. Shukla, V., Scholar, R.: Techniques for solubility enhancement of poorly soluble drugs: an overview. J. Med. Pharm. Appl. Sci. 1, 18–38 (2012)

    Google Scholar 

  5. Jouyban, A.: Review of the cosolvency models for predicting solubility of drugs in water-cosolvent mixtures. J. Pharm. Pharm. Sci. 11, 32–58 (2008)

    Article  CAS  PubMed  Google Scholar 

  6. Jouyban, A.: Review of the cosolvency models for predicting drug solubility in solvent mixtures: an update. J. Pharm. Pharm. Sci. 22, 466–485 (2019)

    Article  CAS  PubMed  Google Scholar 

  7. Barzegar-Jalali, M., Mazaher Haji Agha, E., Adibkia, K., Martinez, F., Jouyban, A.: The solubility of ketoconazole in binary carbitol + water mixtures at T = (293.2–313.2) K. J. Mol. Liq. 297, 111756 (2020)

    Article  CAS  Google Scholar 

  8. Hatefi, A., Rahimpour, E., Ghafourian, T., Martinez, F., Barzegar-Jalali, M., Jouyban, A.: Solubility of ketoconazole in N-methyl-2-pyrrolidone + water mixtures at T = (293.2 to 313.2) K. J. Mol. Liq. 281, 150–155 (2019)

    Article  CAS  Google Scholar 

  9. Hatefi, A., Rahimpour, E., Martinez, F., Barzegar-Jalali, M., Jouyban, A.: Ketoconazole solubility in aqueous binary mixtures of 1-propanol at various temperatures. J. Mol. Liq. 292, 111382 (2019)

    Article  CAS  Google Scholar 

  10. Jouyban, A., Acree, W.E., Jr., Martínez, F.: Dissolution thermodynamics and preferential solvation of ketoconazole in some ethanol (1) + water (2) mixtures. J. Mol. Liq. 313, 113579 (2020)

    Article  CAS  Google Scholar 

  11. Zadaliasghar, S., Jouyban, A., Martinez, F., Barzegar-Jalali, M., Rahimpour, E.: Solubility of ketoconazole in the binary mixtures of 2-propanol and water at different temperatures. J. Mol. Liq. 300, 112259 (2020)

    Article  CAS  Google Scholar 

  12. Barzegar-Jalali, M., Mazaher Haji Agha, E., Adibkia, K., Martinez, F., Kuentz, M., Jouyban, A.: Solubility of ketoconazole in 1,4-dioxane + water mixtures at T = (293.2 to 313.2) K. J. Mol. Liq. 306, 112830 (2020)

    Article  CAS  Google Scholar 

  13. Barzegar-Jalali, M., Mazaher Haji Agha, E., Mirheydari, S.N., Adibkia, K., Martinez, F., Jouyban, A.: Measurement and modelling of the solubility for ketoconazole in acetonitrile + water mixtures at T = (293.2 to 313.2) K. Phy. Chem. Liq. 59, 331–344 (2019)

    Article  CAS  Google Scholar 

  14. Jouyban, A., Soleymani, J., Soltanpour, S.: Solubility of ketoconazole in polyethylene glycol 200 + water mixtures at 298.2–318.2 K. J. Solution Chem. 43, 950–958 (2014)

    Article  CAS  Google Scholar 

  15. Zadaliasghar, S., Rahimpour, E., Ghafourian, T., Martinez, F., Barzegar-Jalali, M., Jouyban, A.: Measurement and mathematical modeling of ketoconazole solubility in propylene glycol + water mixtures at various temperatures. J. Mol. Liq. 291, 111246 (2019)

    Article  CAS  Google Scholar 

  16. Soltanpour, S., Nazemi, V.: Solubility of ketoconazole in binary and ternary solvents of polyethylene glycols 200, 400 or 600 with ethanol and water at 298.2 K: data report and analysis. J. Solution Chem. 47, 65–79 (2018)

    Article  CAS  Google Scholar 

  17. Moradi, M., Rahimpour, E., Zhao, H., Martinez, F., Jouyban, A.: Solubility study of ketoconazole in the mixtures of N-methyl-2-pyrrolidone and ethanol at different temperatures. J. Mol. Liq. 326, 115287 (2021)

    Article  CAS  Google Scholar 

  18. Jouyban, A., Fakhree, M.A.A., Shayanfar, A.: Solubility prediction methods for drug/drug like molecules. Recent Pat. Chem. Eng. 1, 220–231 (2008)

    Article  CAS  Google Scholar 

  19. Jouyban-Gharamaleki, V., Jouyban, A., Acree, W.E., Jr., Rahimpour, E.: Smart systems for determination of drug’s solubility. Drug Dev. Ind. Pharm. 45, 177–187 (2019)

    Article  CAS  PubMed  Google Scholar 

  20. Jouyban-Gharamaleki, A., Valaee, L., Barzegar-Jalali, M., Clark, B.J., Acree, W.E., Jr.: Comparison of various cosolvency models for calculating solute solubility in water–cosolvent mixtures. Int. J. Pharm. 177, 93–101 (1999)

    Article  CAS  PubMed  Google Scholar 

  21. Adjei, A., Newburger, J., Martin, A.: Extended hildebrand approach: solubility of caffeine in dioxane–water mixtures. J. Pharm. Sci. 69, 659–661 (1980)

    Article  CAS  PubMed  Google Scholar 

  22. Yalkowsky, S.H., Roseman, T.: In: Yalkowsky, S.H. (ed.) Solubilization of drugs by cosolvents, pp. 91–134. Marcel Dekker Inc., New York (1981)

    Google Scholar 

  23. Williams, N.A., Amidon, G.L.: Excess free energy approach to the estimation of solubility in mixed solvent systems III: ethanol-propylene glycol-water mixtures. J. Pharm. Sci. 73, 18–23 (1984)

    Article  CAS  PubMed  Google Scholar 

  24. Ochsner, A.B., Belloto, R.J., Jr., Sokoloski, T.D.: Prediction of xanthine solubilities using statistical techniques. J. Pharm. Sci. 74, 132–135 (1985)

    Article  CAS  PubMed  Google Scholar 

  25. Acree, W.E., Jr.: Mathematical representation of thermodynamic properties: Part 2. Derivation of the combined nearly ideal binary solvent (NIBS)/Redlich-Kister mathematical representation from a two-body and three-body interactional mixing model. Thermochim. Acta 198, 71–79 (1992)

    Article  CAS  Google Scholar 

  26. Khossravi, D., Connors, K.A.: Solvent effects on chemical processes, I: solubility of aromatic and heterocyclic compounds in binary aqueous—organic solvents. J. Pharm. Sci. 81, 371–379 (1992)

    Article  CAS  PubMed  Google Scholar 

  27. Jouyban-Gharamaleki, A.: The modified Wilson model and predicting drug solubility in water-cosolvent mixtures. Chem. Pharm. Bull. 46, 1058–1061 (1998)

    Article  CAS  Google Scholar 

  28. Ruckenstein, E., Shulgin, I.: Solubility of drugs in aqueous solutions: Part 2: binary nonideal mixed solvent. Int. J. Pharm. 260, 283–291 (2003)

    Article  CAS  PubMed  Google Scholar 

  29. Ruidiaz, M.A., Rodriguez, S.J., Neita, P.C., Cristancho, D.M., Martinez, F.: Performance of the Jouyban-Acree model for correlating the solubility of indomethacin and ethylhexyl triazone in ethyl acetate+ ethanol mixtures. Vitae 17, 309–316 (2010)

    Google Scholar 

  30. Jouyban, A., Soltanpour, S., Soltani, S., Chan, H., Acree, W.E., Jr.: Solubility prediction of drugs in water-cosolvent mixtures using Abraham solvation parameters. J. Pharm. Pharm. Sci. 10, 263–277 (2007)

    CAS  PubMed  Google Scholar 

  31. Jouyban, A., Soltanpour, S., Soltani, S., Tamizi, E., Fakhree, M.A.A., Acree, W.E., Jr.: Prediction of drug solubility in mixed solvents using computed Abraham parameters. J. Mol. Liq. 146, 82–88 (2009)

    Article  CAS  Google Scholar 

  32. Jouyban, A., Shayanfar, A., Ghafourian, T., Acree, W.E., Jr.: Solubility prediction of pharmaceuticals in dioxane+water mixtures at various temperatures: effects of different descriptors and feature selection methods. J. Mol. Liq. 195, 125–131 (2014)

    Article  CAS  Google Scholar 

  33. Rahimpour, E., Barzegar-Jalali, M., Shayanfar, A., Jouyban, A.: Generally trained models to predict drug solubility in N-methyl-2-pyrrolidone + water mixtures at various temperatures. J. Mol. Liq. 254, 34–38 (2018)

    Article  CAS  Google Scholar 

  34. Barzegar-Jalali, M., Rahimpour, E., Martinez, F., Jouyban, A.: Generally trained models to predict drug solubility in methanol + water mixtures. J. Mol. Liq. 264, 631–644 (2018)

    Article  CAS  Google Scholar 

  35. Mohammadian, E., Barzegar-Jalali, M., Rahimpour, E.: Solubility prediction of lamotrigine in cosolvency systems using Abraham and Hansen solvation parameters. J. Mol. Liq. 276, 675–679 (2019)

    Article  CAS  Google Scholar 

  36. Mohammadian, E., Jouyban, A., Barzegar-Jalali, M., Acree, W.E., Jr., Rahimpour, E.: Solubilization of naproxen: experimental data and computational tools. J. Mol. Liq. 288, 110985 (2019)

    Article  CAS  Google Scholar 

  37. Rahimpour, E., Mohammadian, E., Acree, W.E., Jr., Jouyban, A.: Computational tools for solubility prediction of celecoxib in the binary solvent systems. J. Mol. Liq. 299, 112129 (2020)

    Article  CAS  Google Scholar 

  38. Rahimpour, E., Jouyban, A.: Utilizing Abraham and Hansen solvation parameters for solubility prediction of meloxicam in cosolvency systems. J. Mol. Liq. 328, 115400 (2021)

    Article  CAS  Google Scholar 

  39. Aerts, J.: The hoy solubility parameter calculation software. Computer Chemistry Counsultancy, Germany (2005)

    Google Scholar 

  40. Hansen, C., Parameters, H.S.: A user’s handbook. CRC Press, Boca Raton (2000)

    Google Scholar 

  41. Acree, W.E., Jr., Grubbs, L.M., Abraham, M.H.: Prediction of partition coefficients and permeability of drug molecules in biological systems with Abraham model solute descriptors derived from measured solubilities and water-to-organic solvent partition coefficients, pp. 100–102. InTech. Publisher, New York (2012)

    Google Scholar 

  42. Jouyban, A., Acree, W.E., Jr.: Mathematical derivation of the Jouyban-Acree model to represent solute solubility data in mixed solvents at various temperatures. J. Mol. Liq. 256, 541–547 (2018)

    Article  CAS  Google Scholar 

  43. Grant, D.J.W., Mehdizadeh, M., Chow, A.H.L., Fairbrother, J.E.: Non-linear van’t Hoff solubility-temperature plots and their pharmaceutical interpretation. Int. J. Pharm. 18, 25–38 (1984)

    Article  CAS  Google Scholar 

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Acknowledgements

This work was supported by Research Affairs of Tabriz University of Medical Sciences (Tabriz, Iran) under Grant Number 65523.

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Correspondence to Abolghasem Jouyban.

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Karimzadeh, Z., Rahimpour, E., Acree, W.E. et al. Employing Abraham and Hansen Parameters for Solubility Prediction of Ketoconazole in Binary Solvents at Various Temperatures. J Solution Chem 51, 1000–1019 (2022). https://doi.org/10.1007/s10953-021-01121-3

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