Solubility and preferential solvation of acetaminophen in methanol + water mixtures at 298.15 K

References

• 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. p. 1524–1542.
   Google Scholar
• Budavari S, O’Neil MJ, Smith A, et al. The Merck index: an encyclopedia of chemicals, drugs, and biologicals [Monographs]. 13th ed. Whitehouse Station (NJ): Merck; 2001. p. 10.
   Google Scholar
• Jouyban A. Handbook of solubility data for pharmaceuticals. Boca Raton (FL): CRC Press; 2010.
   Google Scholar
• Pérez DC, Guevara CC, Cárdenas CA, et al. Solubilidad y volúmenes de desplazamiento del acetaminofén en mezclas binarias formadas por agua, etanol y propilenoglicol a 25.0 °C. Rev Colomb Cienc Quím Farm. 2003;32:116–136.
   Google Scholar
• Jiménez JA, Martínez F. Temperature dependence of the solubility of acetaminophen in propylene glycol + ethanol mixtures. J Solution Chem. 2006;35:335–352. DOI:10.1007/s10953-005-9007-8.
   Web of Science ®Google Scholar
• Jiménez JA, Martínez F. Thermodynamic study of the solubility of acetaminophen in propylene glycol + water cosolvent mixtures. J Braz Chem Soc. 2006;17:125–134. DOI:10.1590/S0103-50532006000100018.
   Web of Science ®Google Scholar
• Jiménez JA, Martínez F. Thermodynamic magnitudes of mixing and solvation of acetaminophen in ethanol + water cosolvent mixtures. Rev Acad Colomb Cienc. 2006;30:87–99.
   Google Scholar
• Ahumada EA, Delgado DR, Martínez F. Solution thermodynamics of acetaminophen in some PEG 400 + water mixtures. Fluid Phase Equilib. 2012;332:120–127. DOI:10.1016/j.fluid.2012.07.004.
   Web of Science ®Google Scholar
• Ahumada EA, Delgado DR, Martínez F. Corrigendum to “Solution thermodynamics of acetaminophen in some PEG 400+ water mixtures” [Fluid Phase Equilibr. 332 (2012) 120–127]. Fluid Phase Equilib. 2012;334:204. DOI:10.1016/j.fluid.2012.08.017.
   Web of Science ®Google Scholar
• Rubino JT. Cosolvents and cosolvency. In: Swarbrick J, Boylan JC, editors. Encyclopedia of pharmaceutical technology. Vol. 3. New York: Marcel Dekker; 1988. p. 375–398.
   Google Scholar
• Marcus Y. Solvent mixtures: properties and selective solvation. New York: Marcel Dekker; 2002.
   Google Scholar
• Marcus Y. On the preferential solvation of drugs and PAHs in binary solvent mixtures. J Mol Liq. 2008;140:61–67. DOI:10.1016/j.molliq.2008.01.005.
   Web of Science ®Google Scholar
• Marcus Y. Preferential solvation of ibuprofen and naproxen in aqueous 1,2-propanediol. Acta Chim Slov. 2009;56:40–44.
   Web of Science ®Google Scholar
• Martínez F. Aplicación del método extendido de Hildebrand al estudio de la solubilidad del acetaminofén en mezclas etanol-propilenoglicol. Acta Farm Bonaerense. 2005;24:215–224.
   Google Scholar
• Martínez F. Utilidad del método extendido de Hildebrand en el estudio de la solubilidad del acetaminofén en mezclas agua-propilenoglicol. Rev Acad Colomb Cienc. 2005;29:429–438.
   Google Scholar
• 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;41:433–448.
   Google Scholar
• Delgado DR, Peña MÁ, Martínez F. Preferential solvation of acetaminophen in ethanol + water solvent mixtures according to the inverse Kirkwood-Buff integrals method. Rev Colomb Cienc Quím Farm. 2013;42:298–314.
   Google Scholar
• Peña MÁ, Delgado DR, Martínez F. Preferential solvation of acetaminophen in propylene glycol + water co-solvent mixtures. J Appl Sol Chem Model [Internet]. 2014;3:65–73. DOI:10.6000/1929-5030.2014.03.02.4.
   Google Scholar
• Delgado DR, Jouyban A, Martínez F. Solubility and preferential solvation of meloxicam in methanol + water mixtures at 298.15 K. J Mol Liq. 2014;197:368–373. DOI:10.1016/j.molliq.2014.06.006.
   Web of Science ®Google Scholar
• Cárdenas ZJ, Jiménez DM, Rodríguez GA, et al. Solubility of methocarbamol in some cosolvent+water mixtures at 298.15K and correlation with the Jouyban–Acree model. J Mol Liq. 2013;188:162–166. DOI:10.1016/j.molliq.2013.10.012.
   Web of Science ®Google Scholar
• Jiménez DM, Cárdenas ZJ, Delgado DR, et al. Preferential solvation of methocarbamol in aqueous binary cosolvent mixtures at 298.15 K. Phys Chem Liq. 2014;52:726–737. DOI:10.1080/00319104.2014.915755.
   Web of Science ®Google Scholar
• Delgado DR, Martínez F. Solubility and preferential solvation of sulfadiazine in methanol + water mixtures at several temperatures. Fluid Phase Equilib. 2014;379:128–138. DOI:10.1016/j.fluid.2014.07.013.
   Web of Science ®Google Scholar
• Delgado DR, Martínez F. Solution thermodynamics and preferential solvation of sulfamerazine in methanol + water mixtures. J Solution Chem. 2015;44:360–377. DOI:10.1007/s10953-015-0317-1.
   Web of Science ®Google Scholar
• Marcus Y. The properties of solvents. Chichester: John Wiley & Sons; 1998.
   Google Scholar
• Tewes F, Boury F, Benoit JP. Biodegradable microspheres: advances in production technology. In: Benita S, ed. Microencapsulation: methods and industrial applications. 2nd ed. New York (NY): Taylor & Francis Group, LLC; 2006. p. 1–53.
   Google Scholar
• Kazakevich Y, Lobrutto R. HPLC for pharmaceutical scientists. Hoboken (NJ): John Wiley & Sons; 2007.
   Google Scholar
• US Pharmacopeia. 31st ed. Rockville (MD): United States Pharmacopeial Convention; 2008.
   Google Scholar
• Rodríguez GA, Delgado DR, Martínez F, et al. Solubility of naproxen in ethyl acetate + ethanol mixtures at several temperatures and correlation with the Jouyban-Acree model. Fluid Phase Equilib. 2012;320:49–55. DOI:10.1016/j.fluid.2012.02.009.
   Web of Science ®Google Scholar
• Barton AFM. Handbook of solubility parameters and other cohesion parameters. 2nd ed. New York: CRC Press; 1991.
   Google Scholar
• Martin A, Bustamante P, Chun AHC. Physical chemical principles in the pharmaceutical sciences. 4th ed. Philadelphia (PA): Lea & Febiger; 1993.
   Google Scholar
• Jouyban A. Review of the cosolvency models for predicting solubility of drugs in water-cosolvent mixtures. J Pharm Pharmaceut Sci. 2008;11:32–58.
   PubMed Web of Science ®Google Scholar
• Yalkowsky SH, Roseman TJ. Solubilization of drugs by cosolvents. In: Yalkowsky SH, ed. Techniques of solubilization of drugs. New York (NY): Marcel Dekker; 1981. p. 91–134.
   Google Scholar
• Rubino JT, Obeng E. Influence of solute structure on deviations from the log-linear solubility equation in propylene glycol:water mixtures. J Pharm Sci. 1991;80:479–483. DOI:10.1002/jps.2600800516.
   PubMed Web of Science ®Google Scholar
• Jouyban-Gharamaleki A, Valaee L, Barzegar-Jalali M, et al. Comparison of various cosolvency models for calculating solute solubility in water-cosolvent mixtures. Int J Pharm. 1999;177:93–101. DOI:10.1016/S0378-5173(98)00333-0.
   PubMed Web of Science ®Google Scholar
• Jouyban-Gharamaleki A, Acree Jr WE. Comparison of models for describing multiple peaks in solubility profiles. Int J Pharm. 1998;167:177–182. DOI:10.1016/S0378-5173(98)00073-8.
   Web of Science ®Google Scholar
• Jouyban-Gharamaleki A, Hanaee J. A novel method for improvement of predictability of the CNIBS/R-K equation. Int J Pharm. 1997;154:245–247. DOI:10.1016/S0378-5173(97)00136-1.
   Web of Science ®Google Scholar
• Jouyban A, Soltanpour SH, Soltani S, et al. Prediction of drug solubility in mixed solvents using computed Abraham parameters. J Mol Liq. 2009;146:82–88. DOI:10.1016/j.molliq.2009.02.003.
   Web of Science ®Google Scholar
• Li A, Yalkowsky SH. Predicting cosolvency. 1. Solubility ratio and solute logKow. Ind Eng Chem Res. 1998;37:4470–4475. DOI:10.1021/ie980232v.
   Web of Science ®Google Scholar
• Avila CM, Martínez F. Thermodynamic study of the solubility of benzocaine in some organic and aqueous solvents. J Solution Chem. 2002;31:975–985. DOI:10.1023/A:1021825509697.
   Web of Science ®Google Scholar
• Martínez F, Peña MÁ, Bustamante P. Thermodynamic analysis and enthalpy-entropy compensation for the solubility of indomethacin in aqueous and non-aqueous mixtures. Fluid Phase Equilib. 2011;308:98–106. DOI:10.1016/j.fluid.2011.06.016.
   Web of Science ®Google Scholar
• 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. 1995;91:995–998. DOI:10.1039/FT9959100995.
   Google Scholar
• Holguín AR, Delgado DR, Martínez F, et al. Solution thermodynamics and preferential solvation of meloxicam in propylene glycol + water mixtures. J Solution Chem. 2011;40:1987–1999. DOI:10.1007/s10953-011-9769-0.
   Web of Science ®Google Scholar
• Mora CP, Martínez F. Thermodynamic quantities relative to solution processes of naproxen in aqueous media at pH 1.2 and 7.4. Phys Chem Liq. 2006;44:585–596. DOI:10.1080/00319100701313862.
   Web of Science ®Google Scholar
• Ben-Naim A. Theory of preferential solvation of nonelectrolytes. Cell Biophys. 1988;12:255–269. DOI:10.1007/BF02918361.
   PubMedGoogle Scholar
• Ben-Naim A. Preferential solvation in two- and in three-component systems. Pure Appl Chem. 1990;62:25–34. DOI:10.1351/pac199062010025.
   Web of Science ®Google Scholar
• Marcus Y. Solubility and solvation in mixed solvent systems. Pure Appl Chem. 1990;62:2069–2076. DOI:10.1351/pac199062112069.
   Web of Science ®Google Scholar
• Newman KE. Kirkwood-Buff solution theory: derivation and applications. Chem Soc Rev. 1994;23:31–40. DOI:10.1039/CS9942300031.
   Web of Science ®Google Scholar
• Delgado DR, Martínez F. Preferential solvation of sulfadiazine, sulfamerazine and sulfamethazine in ethanol + water solvent mixtures according to the IKBI method. J Mol Liq. 2014;193:152–159. DOI:10.1016/j.molliq.2013.12.021.
   Web of Science ®Google Scholar
• Peña MÁ, Delgado DR, Martínez F. Preferential solvation of some n-alkyl p-substituted-benzoates in propylene glycol + water co-solvent mixtures. Phys Chem Liq. 2015;53:455–466. DOI:10.1080/00319104.2015.1006221.
   Web of Science ®Google Scholar
• Delgado DR, Martínez F. Preferential solvation of some structurally related sulfonamides in 1-propanol + water co-solvent mixtures. Phys Chem Liq. 2015;53:293–306. DOI:10.1080/00319104.2014.961191.
   Web of Science ®Google Scholar
• Fedors RF. A method for estimating both the solubility parameters and molar volumes of liquids. Polym Eng Sci. 1974;14:147–154. DOI:10.1002/pen.760140211.
   Web of Science ®Google Scholar
• 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. DOI:10.1021/ja00418a009.
   Web of Science ®Google Scholar
• Mikhail SZ, Kimel WR. Densities and viscosities of methanol-water mixtures. J Chem Eng Data. 1961;6:533–537. DOI:10.1021/je60011a015.
   Google Scholar