Abstract
The preferential solvation parameters of ketoprofen (KTP) in ethanol (EtOH) + water and propylene glycol (PG) + water binary solvent mixtures were obtained from their thermodynamic properties by means of the inverse Kirkwood–Buff integrals (IKBI) and quasi-lattice quasi-chemical methods. According to the IKBI method, it is found that KTP is very sensitive to specific solvation effects, so the preferential solvation parameter by co-solvents, δx 1,3, is negative in the water-rich mixtures of both binary systems but positive in the other compositions at temperatures of 293.15, 303.15 and 313.15 K. From this it can be assumed that, in water-rich mixtures, hydrophobic hydration around the aromatic rings and the methyl group, present in the drug, plays a relevant role in the solvation. The bigger amount of drug solvation by the co-solvent in mixtures of similar solvent proportions and in co-solvent-rich mixtures could be due mainly to polarity effects. Moreover, in these mixtures the solute will be acting as a Lewis acid with the co-solvent molecules, because they are more basic than water.
Similar content being viewed by others
References
Hanson, G.R.: Analgesic, antipyretic, and antiinflammatory drugs. In: Gennaro, A.R. (ed.) Remington, The Science and Practice of Pharmacy, 20th edn. Lippincott, Williams & Wilkins, Philadelphia (2000)
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, NJ (2001)
Jouyban, A.: Handbook of Solubility Data for Pharmaceuticals. CRC Press, Taylor & Francis Group, Boca Raton (2010)
Gantiva, M., Yurquina, A., Martínez, F.: Solution thermodynamics of ketoprofen in ethanol + water cosolvent mixtures. J. Chem. Eng. Data 55, 113–118 (2010)
Gantiva, M., Martínez, F.: Thermodynamic analysis of the solubility of ketoprofen in some propylene glycol + water cosolvent mixtures. Fluid Phase Equilib. 293, 242–250 (2010)
Gantiva, M., Martínez, F.: Método extendido de Hildebrand en la predicción de la solubilidad del ketoprofeno en mezclas cosolventes etanol + agua. Quím. Nova 33, 370–376 (2010)
Gantiva, M., Yurquina, A., Martínez, F.: Desempeño de los modelos de Yalkowsky & Roseman y de Jouyban & Acree en la estimación de la solubilidad del ketoprofeno en mezclas cosolventes etanol + agua. Vitae Rev. Fac. Quím. Farm. 16, 361–368 (2009)
Gantiva, M., Vargas, E.F., Manzur, M.E., Yurquina, A., Martínez, F.: Modelos de Yalkowsky-Roseman y Jouyban-Acree en la estimación de la solubilidad del ketoprofeno en algunas mezclas cosolventes propilenoglicol + agua. Rev. Colomb. Cienc. Quím. Farm. 38, 156–171 (2009)
Ben-Naim, A.: Preferential solvation in two- and in three-component systems. Pure Appl. Chem. 62, 25–34 (1990)
Marcus, Y.: Solubility and solvation in mixed solvent systems. Pure Appl. Chem. 62, 2069–2076 (1990)
Marcus, Y.: Solvent Mixtures: Properties and Selective Solvation. Marcel Dekker Inc, New York (2002)
Marcus, Y.: Preferential solvation in mixed solvents. In: Smith, P.E., Matteoli, E., O’Connell, J.P. (eds.) Fluctuation Theory of Solutions: Applications in Chemistry, Chemical Engineering, and Biophysics. CRC Press, Taylor & Francis Group, Boca Raton (2013)
Marcus, Y.: On the preferential solvation of drugs and PAHs in binary solvent mixtures. J. Mol. Liq. 140, 61–67 (2008)
Marcus, Y.: Preferential solvation of ibuprofen and naproxen in aqueous 1,2-propanediol. Acta Chim. Slov. 56, 40–44 (2009)
Ruidiaz, M.A., Delgado, D.R., Martínez, F., Marcus, Y.: Solubility and preferential solvation of indomethacin in 1,4-dioxane + water solvent mixtures. Fluid Phase Equilib. 299, 259–265 (2010)
Delgado, D.R., Holguín, A.R., Almanza, O.A., Martínez, F., Marcus, Y.: Solubility and preferential solvation of meloxicam in ethanol + water solvent mixtures. Fluid Phase Equilib. 305, 88–95 (2011)
Holguín, A.R., Delgado, D.R., Martínez, F., Marcus, Y.: Solution thermodynamics and preferential solvation of meloxicam in propylene glycol + water mixtures. J. Solution Chem. 40, 1987–1999 (2011)
Delgado, D.R., Peña, M.Á., Martínez, F.: Preferential solvation of acetaminophen in ethanol + water solvent mixtures according to the inverse Kirkwood–Buff integrals method. Rev. Colomb. Cienc. Quím. Farm. 42, 298–314 (2013)
Delgado, D.R., Martínez, F.: Preferential solvation of sulfadiazine, sulfamerazine and sulfamethazine in ethanol + water solvent mixtures according to the IKBI method. J. Mol. Liq. 193, 152–159 (2014)
Delgado, D.R., Peña, M.Á., Martínez, F.: Preferential solvation of some sulfonamides in propylene glycol + water solvent mixtures according to the IKBI and QLQC methods. J. Solution Chem. 43, 360–374 (2014)
Rubino, J.T.: Cosolvents and cosolvency. In: Swarbrick, J., Boylan, J.C. (eds.) Encyclopedia of Pharmaceutical Technology, vol. 3. Marcel Dekker Inc, New York (1988)
Yalkowsky, S.H.: Solubility and Solubilization in Aqueous Media. American Chemical Society and Oxford University Press, New York (1999)
Marcus, Y.: The Properties of Solvents. John Wiley & Sons, Chichester (1998)
Connors, K.A.: Thermodynamics of Pharmaceutical Systems: An Introduction for Students of Pharmacy. Wiley-Interscience, Hoboken (2002)
Fedors, R.F.: A method for estimating both the solubility parameters and molar volumes of liquids. Polym. Eng. Sci. 14, 147–154 (1974)
Jiménez, J., Manrique, J., Martínez, F.: Effect of temperature on some volumetric properties for ethanol + water mixtures. Rev. Colomb. Cienc. Quím. Farm. 33, 145–155 (2004)
Jiménez, J., Martínez, F.: Study of some volumetric properties of 1,2-propanediol + water mixtures at several temperatures. Rev. Colomb. Cienc. Quím. Farm. 34, 46–57 (2005)
Yalkowsky, S.H., Roseman, T.J.: Solubilization of drugs by cosolvents. In: Yalkowsky, S.H. (ed.) Techniques of Solubilization of Drugs. Marcel Dekker, New York (1981)
Barton, A.F.M.: Handbook of Solubility Parameters and Other Cohesion Parameters, 2nd edn edn. CRC Press, New York (1991)
Kamlet, M.J., Taft, R.W.: The solvatochromic comparison method. I. The beta-scale of solvent hydrogen-bond acceptor (HBA) basicities. J. Am. Chem. Soc. 98, 377–383 (1976)
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Cárdenas, Z.J., Jiménez, D.M. & Martínez, F. Preferential Solvation of Ketoprofen in Some Co-solvent Binary Mixtures. J Solution Chem 43, 1904–1915 (2014). https://doi.org/10.1007/s10953-014-0255-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10953-014-0255-3