Solubility Prediction of Paracetamol in N-Methyl-2-pyrrolidone + Ethanol + Water Mixtures at 25 °C
DOI:
https://doi.org/10.6000/1929-5030.2014.03.03.4Keywords:
Paracetamol, binary solvents, ternary solvents, solubility prediction, pharmaceutical cosolvents.Abstract
The solubility of paracetamol in N-Methyl-2-pyrrolidone (NMP) + ethanol and NMP + ethanol + water solvent mixtures at 25°C was determined using the shake flask method. The generated data extended the solubility database of pharmaceuticals and also was used to assess the solubility prediction capability of the Jouyban-Acree model in NMP + ethanol + water mixtures. The accuracy of the predicted solubilities was evaluated by the mean percentage deviation (MPD) between the predicted and experimental solubilities. The MPD of the Jouyban-Acree model for predicting the solubility of paracetamol in NMP + ethanol + water mixtures at 25°C was 14.6 %.
References
[1] Yalkowsky SH, Ed., Solubilization of drugs by cosolvents. New York, Marcel Dekker, 1981.
[2] Acree Jr WE. Mathematical representation of thermodynamic properties. Part II. 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 1992; 198: 71-9. http://dx.doi.org/10.1016/0040-6031(92)85059-5
[3] Jouyban-Gharamaleki A, Acree Jr WE. Comparison of models for describing multiple peaks in solubility profiles. Int J Pharm 1998; 167: 177-82. http://dx.doi.org/10.1016/S0378-5173(98)00073-8
[4] Jouyban-Gharamaleki A, Khaledi MG, Clark BJ. Calculation of electrophoretic mobilities in water-organic modifier mixtures in capillary electrophoresis. J Chromatogr A 2000; 868: 277-84. http://dx.doi.org/10.1016/S0021-9673(99)01258-3
[5] Jouyban A, Chan HK, Barzegar-Jalali M, Acree Jr WE. A model to represent solvent effects on chemical stability of solutes in mixed solvent systems. Int J Pharm 2002; 243 167-72. http://dx.doi.org/10.1016/S0378-5173(02)00276-4
[6] Jouyban A, Chan HK, Clark BJ, Acree Jr WE. Mathematical representation of apparent acid dissociation constants in aqueous-organic solvent mixtures. Int J Pharm 2002; 246: 135-42. http://dx.doi.org/10.1016/S0378-5173(02)00355-1
[7] Jouyban A, Soltani S, Chan HK, Acree Jr WE. Modeling acid dissociation constant of analytes in binary solvents at various temperatures using Jouyban-Acree model. Thermochim Acta 2005; 428: 119-23. http://dx.doi.org/10.1016/j.tca.2004.11.002
[8] Jouyban A, Rashidi MR, Vaez-Gharamaleki Z, Matin AA, Djozan Dj. Mathematical representation of analyte's capacity factor in binary solvent mobile phases using Jouyban-Acree model. Pharmazie 2005; 60: 827-9.
[9] Jouyban A, Soltanpour Sh, Chan HK. A simple relationship between dielectric constant of mixed solvents with solvent composition and temperature. Int J Pharm 2004; 269: 353- 60. http://dx.doi.org/10.1016/j.ijpharm.2003.09.010
[10] Jouyban A, Fathi-Azarbayjani A, Acree Jr WE. Surface tension calculation of mixed solvents with respect to solvent composition and temperature by using Jouyban-Acree model. Chem Pharm Bull 2004; 52: 1219-22. http://dx.doi.org/10.1248/cpb.52.1219
[11] Jouyban A, Khoubnasabjafari M, Vaez-Gharamaleki Z, Fekari Z, Acree Jr WE. Calculation of the viscosity of binary liquids at various temperatures using Jouyban-Acree model. Chem Pharm Bull 2005; 53: 519-23. http://dx.doi.org/10.1248/cpb.53.519
[12] Jouyban A, Fathi-Azarbayjani A, Khoubnasabjafari M, Acree Jr WE. Mathematical representation of the density of liquid mixtures at various temperatures using Jouyban-Acree model. Indian J Chem A 2005; 44: 1553-560.
[13] Jouyban A, Khoubnasabjafari M, Acree Jr WE. Modeling the solvatochromic parameter ( ET N ) of mixed solvents with respect to solvent composition and temperature using Jouyban-Acree model. Daru 2006; 14: 22-5.
[14] Jouyban A, Soltani S, Khoubnasabjafari M, Acree Jr WE. Refractive index correlation of solvent mixtures at various temperatures. Asian J Chem 2006; 18: 2037-40.
[15] Hasan M, Shirude DF, Hiray AP, Sawant AB, Kadam UB. Densities, viscosities and ultrasonic velocities of binary mixtures of methylbenzene with hexan-2-ol, heptan-2-ol and octan-2-ol at T = 298.15 and 308.15 K. Fluid Phase Equilib 2006; 252: 88-95. http://dx.doi.org/10.1016/j.fluid.2007.01.001
[16] Jouyban A. In silico prediction of drug solubility in waterdioxane mixtures using Jouyban-Acree model. Pharmazie 2007; 62: 46-50.
[17] Jouyban A, Acree Jr WE. In silico prediction of drug solubility in water-ethanol mixtures using Jouyban-Acree model. J Pharm Pharmaceut Sci 2006; 9: 262-9.
[18] Jouyban A. Prediction of drug solubility in water-propylene glycol mixtures using Jouyban-Acree model. Pharmazie 2007; 62: 365-7.
[19] Jouyban A. Solubility prediction of drugs in water-PEG 400 mixtures. Chem Pharm Bull 2006; 54: 1561-6. http://dx.doi.org/10.1248/cpb.54.1561
[20] Jouyban A, Fakhree MAA, Mirzaei Sh, Ghafourian T, Soltanpour Sh, Nokhodchi A. Solubility prediction of paracetamol in water-glycerol mixtures at 25 and 30 °C using Jouyban-Acree model. Asian J Chem 2009; 21: 7249-53.
[21] Soltanpour Sh, Jouyban A. Solubility of acetaminophen and ibuprofen in polyethylene glycol 600, N-methyl pyrrolidone and water mixtures. J Solution Chem 2011; 40: 2032-45. http://dx.doi.org/10.1007/s10953-011-9767-2
[22] Jouyban A, Acree Jr WE. Prediction of drug solubility in ethanol-ethyl acetate mixtures at various temperatures using the Jouyban-Acree model. J Drug Del Sci Technol 2007; 17: 159-60.
[23] Jouyban A, Khoubnasabjafari M, Martinez F. A model to predict the solubility of drugs in ethanol + propylene glycol mixtures at various temperatures. Submitted.
[24] Jouyban A. Handbook of Solubility Data for Pharmaceuticals. CRC Press, Boca Raton, 2010.
[25] Soltanpour Sh, Jouyban A. Solubility of acetaminophen and ibuprofen in binary and ternary mixtures of polyethylene glycol 600, ethanol and water. Chem Pharm Bull 2010; 58: 219-24. http://dx.doi.org/10.1248/cpb.58.219
[26] Jouyban A, Fakhree MAA. Experimental and computational methods pertaining to drug solubility. In: Acree Jr WE. Editor. Toxicity and Drug Testing. InTech Co., New York, 2012.
[27] Jouyban-Gharamaleki A, Valaee L, Barzegar-Jalali M, Clark BJ, Acree Jr WE. Comparison of various cosolvency models for calculating solute solubility in water-cosolvent mixtures. Int J Pharm 1999; 177: 93-101. http://dx.doi.org/10.1016/S0378-5173(98)00333-0
[28] Jouyban-Gharamaleki A, Clark BJ, Acree Jr WE. Models to predict solubility in ternary solvents based on sub-binary experimental data. Chem Pharm Bull 2000, 48: 1866-71. http://dx.doi.org/10.1248/cpb.48.1866
Downloads
Published
2014-09-18
Issue
Section
General Articles
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 .
How to Cite
Solubility Prediction of Paracetamol in N-Methyl-2-pyrrolidone + Ethanol + Water Mixtures at 25 °C. (2014). Journal of Applied Solution Chemistry and Modeling, 3(3), 164-168. https://doi.org/10.6000/1929-5030.2014.03.03.4
