Preferential Solvation of Acetaminophen in Propylene Glycol + Water Co-Solvent Mixtures
DOI:
https://doi.org/10.6000/1929-5030.2014.03.02.4Keywords:
Acetaminophen, propylene glycol, solubility, inverse Kirkwood-Buff integrals, preferential solvation.Abstract
The preferential solvation parameters defined as the differences between the local mole fraction of solvents around analgesic drug acetaminophen and those for the bulk co-solvent composition in propylene glycol + water mixtures were derived from their thermodynamic properties by means of the inverse Kirkwood-Buff integrals (IKBI) and the quasi-lattice-quasi-chemical (QLQC) methods. It is found that acetaminophen is sensitive to solvation effects, so according to IKBI method the preferential solvation parameter δ´xPG,A, is negative in water-rich mixtures but positive in medium compositions and in co-solvent-rich mixtures. It is conjecturable that in water-rich mixtures the hydrophobic hydration around the aromatic ring and methyl group present in the drug plays a relevant role in the solvation. The bigger drug solvation by co-solvent in mixtures of similar solvent proportions and in propylene glycol-rich mixtures could be due mainly to polarity effects. Otherwise, according to QLQC method, this drug is preferentially solvated by the co-solvent in all the mixtures.
References
[1] Raffa RB. Analgesic, antipyretic, and anti-inflammatory drugs. In: Gennaro A, editor. Remington: The Science and Practice of Pharmacy. 21st ed. Philadelphia: Lippincott Williams & Wilkins 2005.
[2] Jiménez J, Martinez F. Thermodynamic study of the solubility of acetaminophen in propylene glycol + water cosolvent mixtures. J Braz Chem Soc 2006; 17: 125-134. http://dx.doi.org/10.1590/S0103-50532006000100018
[3] Jouyban A. Handbook of Solubility Data for Pharmaceuticals. Boca Raton, FL: CRC Press; 2010.
[4] Rubino JT. Cosolvents and cosolvency. In: Swarbrick J, Boylan JC, editors. Encyclopedia of Pharmaceutical Technology, vol 3. New York: Marcel Dekker, Inc.; 1988.
[5] Jiménez J, Martínez F. Thermodynamic magnitudes of mixing and solvation of acetaminophen in ethanol + water cosolvent mixtures. Rev Acad Colomb Cienc 2006; 30: 87- 99.
[6] Delgado DR, Peña MA, Martínez F. Preferential solvation of acetaminophen in ethanol + water solvent mixtures according to the inverse Kirkwood-Buff integrals method. Rev Colomb Cienc Quim Farm 2013; 42: 298-314.
[7] Marcus Y. Preferential solvation of ibuprofen and naproxen in aqueous 1,2-propanediol. Acta Chim Slov 2009; 56: 40-44.
[8] Ruidiaz MA, Delgado DR, Martínez F, Marcus Y. Solubility and preferential solvation of indomethacin in 1,4-dioxane + water solvent mixtures. Fluid Phase Equilib 2010; 299: 259- 265. http://dx.doi.org/10.1016/j.fluid.2010.09.027
[9] Delgado DR, Holguín AR, Almanza OA, Martínez F, Marcus Y. Solubility and preferential solvation of meloxicam in ethanol + water mixtures. Fluid Phase Equilib. 2011; 305: 88- 95. http://dx.doi.org/10.1016/j.fluid.2011.03.012
[10] Holguín AR, Delgado DR, Martínez F, Marcus Y. Solution thermodynamics and preferential solvation of meloxicam in propylene glycol + water mixtures. J. Solution Chem 2011; 40: 1987-1999. http://dx.doi.org/10.1007/s10953-011-9769-0
[11] Ben-Naim A. Theory of preferential solvation of nonelectrolytes. Cell Biophysics 1988; 12: 255-269. http://dx.doi.org/10.1007/BF02918361
[12] Ben-Naim A. Preferential solvation in two- and in threecomponent systems. Pure & Appl Chem 1990; 62: 25-34. http://dx.doi.org/10.1351/pac199062010025
[13] Marcus Y. Solubility and solvation in mixed solvent systems. Pure & Appl Chem 1990; 62: 2069-2076. http://dx.doi.org/10.1351/pac199062112069
[14] Marcus Y. Solvent Mixtures: Properties and Selective Solvation. New York: Marcel Dekker, Inc.; 2002.
[15] Marcus Y. On the preferential solvation of drugs and PAHs in binary solvent mixtures. J Mol Liq 2008; 140: 61-67. http://dx.doi.org/10.1016/j.molliq.2008.01.005
[16] Newman KE. Kirkwood-Buff solution theory: Derivation and applications. Chem Soc Rev 1994; 23: 31-40. http://dx.doi.org/10.1039/cs9942300031
[17] Delgado DR, Peña MA, Martínez F. Preferential solvation of some sulfonamides in propylene glycol + water solvent mixtures according to the IKBI and QLQC methods. J Solution Chem 2014; 43: 360-374. http://dx.doi.org/10.1007/s10953-014-0130-2
[18] Fedors RF. A method for estimating both the solubility parameters and molar volumes of liquids. Polym Eng Sci 1974; 14: 147-154. http://dx.doi.org/10.1002/pen.760140211
[19] Ahumada EA, Delgado DR, Martínez F. Acetaminophen solubility in polyethylene glycol 400 + water mixtures according to the extended Hildebrand solubility approach. Rev Colomb Quím 2012; 41: 433-438.
[20] Jiménez J, Martínez F. Study of some volumetric properties of 1,2-propanediol + water mixtures at several temperatures. Rev Colomb Cienc Quím Farm 2005; 34: 46-57.
[21] Kamlet MJ, Taft RW. The solvatochromic comparison method. I. The beta-scale of solvent hydrogen-bond acceptor (HBA) basicities. J Am Chem Soc 1976; 98: 377-383. http://dx.doi.org/10.1021/ja00418a009
[22] Taft RW, Kamlet MJ. The solvatochromic comparison method. II. The alpha-scale of solvent hydrogen-bond donor (HBD) acidities. J Am Chem Soc 1976; 98: 2886-2894. http://dx.doi.org/10.1021/ja00426a036
Downloads
Published
How to Cite
Issue
Section
License
Policy for Journals/Articles with Open Access
Authors who publish with this journal agree to the following terms:
- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
- Authors are permitted and encouraged to post links to their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work
Policy for Journals / Manuscript with Paid Access
Authors who publish with this journal agree to the following terms:
- Publisher retain copyright .
- Authors are permitted and encouraged to post links to their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work .