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Received November 22, 2016
Accepted February 6, 2017
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Solubility of celecoxib in N-methyl-2-pyrrolidone+water mixtures at various temperatures: Experimental data and thermodynamic analysis
Sarah Nozohouri1
Ali Shayanfar2
Zaira Johanna Cárdenas3
Fleming Martinez3
and Abolghasem Jouyban4 5†
1Liver and Gastrointestinal Diseases Research Center, Tabriz University of Medical Sciences, Tabriz 51664, Iran 2Food and Drug Safety Research Center and Faculty of Pharmacy, Tabriz University of Medical Sciences, Tabriz, Iran 3Grupo de Investigaciones Farmacéutico-Fisicoquímicas, Departamento de Farmacia, Facultad de Ciencias, Universidad Nacional de Colombia, Sede Bogotá, Cra. 30 No. 45-03, Bogotá, D.C., Colombia 4Pharmaceutical Analysis Research Center and Faculty of Pharmacy, Tabriz University of Medical Sciences, Tabriz 51664, Iran 5Kimia Idea Pardaz Azarbayjan (KIPA) Science Based Company, Tabriz University of Medical Sciences, Tabriz 51664, Iran
Korean Journal of Chemical Engineering, May 2017, 34(5), 1435-1443(9), 10.1007/s11814-017-0028-y
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Abstract
Solubility is one of the most significant physicochemical properties of drugs, and improving the solubility of drugs is still a challenging subject in pharmaceutical sciences due to requirements of enhancing their bioavailability. Celecoxib, according to the biopharmaceutics classification system (BCS), is a class 2 drug, possessing low water solubility (<5 μg·mL-1) and high permeability. Increasing the solubility of this group can lead to improved bioavailability, dose reduction and subsequently, increased efficiency and reduced side effects. In this study, celecoxib solubility was determined in binary mixtures of N-methyl-2-pyrrolidone (NMP)+water at 293.2, 298.2, 303.2, 308.2 and 313.2 K. The solubility of celecoxib is increased with the addition of NMP to the aqueous solutions and reaches a maximum value in neat NMP. In addition, increased temperature leads to enhanced solubility of celecoxib in a given solvent composition. The solubility data of celecoxib in NMP+water at different temperatures were correlated using different mathematical models including, the Jouyban-Acree model and a combination of the Jouyban-Acree and van’t Hoff models. Thermodynamic parameters, Gibbs energy, enthalpy and entropy of dissolution processes were performed based on Gibbs and van’t Hoff equations. Thermodynamic analysis allowed observing two main entropy or enthalpy-driven dissolution mechanisms, varying according to the composition of aqueous mixtures. Moreover, preferential solvation of celecoxib by water is observed in water-rich mixtures but preferential solvation by NMP was seen in mixtures with similar composition and also in NMP-rich mixtures.
Keywords
References
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Bustamante P, Romero S, Pena A, Escalera B, Reillo A, J. Pharm. Sci., 87, 1590 (1998)
Ruidiaz MA, Delgado DR, Martinez F, Marcus Y, Fluid Phase Equilib., 299(2), 259 (2010)
Sotomayor RG, Holguin AR, Romdhani A, Martinez F, Jouyban A, J. Solution Chem., 42, 358 (2013)
Marcus Y, J. Mol. Liq., 140, 61 (2008)
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Henni A, Hromek JJ, Tontiwachwuthikul P, Chakma A, J. Chem. Eng. Data, 49(2), 231 (2004)
Fedors RF, Polym. Eng. Sci., 14, 147 (1974)
Delgado DR, Pena MA, Martinez F, J. Solution Chem., 43, 360 (2014)
Delgado DR, Almanza OA, Martinez F, Pena MA, Jouyban A, Acree WE, J. Chem. Thermodyn., 97, 264 (2016)
Williams HD, Trevaskis NL, Charman SA, Shanker RM, Charman WN, Pouton CW, Porter CJH, Pharmacol. Rev., 65, 315 (2013)
Yang W, Wu K, Hu Y, Zhang T, Guo Q, Yang S, Shi Y, Korean J. Chem. Eng., 32(6), 1158 (2015)
Huang Z, Yu C, Xue W, Lin F, Zeng Z, Korean J. Chem. Eng., 34(1), 206 (2017)
Yeh MK, Chang LC, Chiou AH, AAPS PharmSciTech., 10, 166 (2009)
Stephens D, Li LC, Pec E, Robinson D, Drug Dev. Ind. Pharm., 25, 961 (1999)
Watkinson R, Guy R, Hadgraft J, Lane M, Skin Pharmacol. Physiol., 22, 225 (2009)
Proniuk S, Liederer BM, Dixon SE, Rein JA, Kallen MA, Blanchard J, J. Pharm. Sci., 91, 101 (2002)
Bendas B, Schmalfuβ U, Neubert R, Int. J. Pharm., 116, 19 (1995)
Rager T, Hilfiker R, Cryst. Growth Des., 10, 3237 (2010)
Porra R, Thompson W. Kriedemann P, Biochim. Biophys. Acta, 975, 384 (1989)
Zhao H, Dong J, Lu J, Chen J, Li Y, Shan L, Lin Y, Fan W, Gu G, J. Agric. Food Chem., 54, 7277 (2006)
Jouyban A, Fakhree MAA, Shayanfar A, J. Pharm. Pharm. Sci., 13, 524 (2010)
Bartsch W, Sponer G, Dietmann K, Fuchs G, Arzneimitt. Forsch., 26, 1581 (1975)
Tarantino R, Bishop E, Chen FC, Iqbal K, Malick AW, J. Pharm. Sci., 83, 1213 (1994)
Sanghvi R, Narazaki R, Machatha SG, Yalkowsky SH, AAPS PharmSciTech., 9, 366 (2008)
Silverstein FE, Faich G, Goldstein JL, Simon LS, Pincus T, Whelton A, Makuch R, Eisen G, Agrawal NM, Stenson WF, Burr AM, Zhao WW, Kent JD, Lefkowith JB, Verburg KM, Geis GS, JAMA, 284, 1247 (2000)
Davies NM, McLachlan AJ, Day RO, Williams KM, Clin. Pharmacokinet., 38, 225 (2000)
Rathi P, Jouyban A, Khoubnasabjafari M, Kale M, J. Chem. Eng. Data, 60(7), 2128 (2015)
Jouyban A, J. Pharm. Pharm. Sci., 11, 32 (2008)
Acree WE, Thermochim. Acta, 198, 71 (1992)
Jouyban-Gharamaleki A, Acree WE, Int. J. Pharm., 167, 177 (1998)
Williams NA, Amidon GL, J. Pharm. Sci., 73, 14 (1984)
Barzegar-Jalali M, Jouyban-Gharamaleki A, Int. J. Pharm., 152, 247 (1997)
Jouyban-Gharamaleki A, Chem. Pharm. Bull., 46, 1058 (1998)
Jouyban A, Chan HK, Romero S, Khoubnasabjafari M, Bustamante P, Pharmazie, 59, 117 (2004)
Barzegar-Jalali M, Hanaee J, Int. J. Pharm., 109, 291 (1994)
Barzegar-Jalali M, Jouyban-Gharamaleki A, Int. J. Pharm., 140, 237 (1996)
Jouyban-Gharamaleki A, Valaee L, Barzegar-Jalali M, Clark B, Acree WE, Int. J. Pharm., 177, 93 (1999)
Jouyban A, J. Pharm. Pharm. Sci., 9, 262 (2006)
Jouyban A, Chew NYK, Chan HK, Sabour M, Acree WE, Chem. Pharm. Bull., 53, 634 (2005)
Jouyban A, Shayanfar A, Panahi-Azar V, Soleymani J, Yousefi BH, Acree WE, York P, J. Pharm. Sci., 100, 4368 (2011)
Jouyban-Gharamaleki A, Hanaee J, Int. J. Pharm., 154, 245 (1997)
Grant D, Mehdizadeh M, Chow AL, Fairbrother J, Int. J. Pharm., 18, 25 (1984)
Eghrary SH, Zarghami R, Martinez F, Jouyban A, J. Chem. Eng. Data, 57(5), 1544 (2012)
Jouyban A, Fakhree MAA, Acree WE, J. Chem. Eng. Data, 57(4), 1344 (2012)
Jouyban A, Fakhree MAA, In: Acree WE, Toxicity and Drug Testing, InTech Publisher, New York, 187 (2012).
Higuchi T, Connors KA, Adv. Anal. Chem. Instr., 4, 117 (1965)
Shayanfar A, Acree WE, Jouyban A, J. Chem. Eng. Data, 54(10), 2964 (2009)
Soltanpour S, Jouyban A, J. Solution Chem., 40, 2032 (2011)
Soltanpour S, Jafari B, Barzegar-Jalali M, Jouyban A, J. Drug Deliv. Sci. Technol., 24, 111 (2014)
Soltanpour S, Acree WE, Jouyban A, AAPS. PharmSciTech., 10, 1153 (2009)
Jouyban A, Shayanfar A, Acree WE, Fluid Phase Equilib., 293(1), 47 (2010)
Barzegar-Jalali M, Mohammadzade M, Martinez F, Jouyban A, J. Mol. Liq., 220, 484 (2016)
Guo X, Cheng YW, Wang LJ, Li X, J. Chem. Eng. Data, 53(7), 1421 (2008)
Jouyban A, Romero S, Chan HK, Clark BJ, Bustamante P, Chem Pharm Bull, 50, 594 (2002)
Millard JW, Alvarez-Nunez F, Yalkowsky S, Int. J. Pharm., 245, 153 (2002)
Jouyban A, Handbook of Solubility Data for Pharmaceuticals, CRC Press, Boca Raton, Florida (2010).
Rodriguez GA, Delgado DR, Martinez F, Jouyban A, Acree WE, Fluid Phase Equilib., 320, 49 (2012)
Vahdati S, Shayanfar A, Hanaee J, Martinez F, Acree WE, Jouyban A, Ind. Eng. Chem. Res., 52(47), 16630 (2013)
Perlovich GL, Kurkov SV, Kinchin AN, Bauer-Brandl A, Eur. J. Pharm. Biopharm., 57, 411 (2004)
Bustamante P, Romero S, Pena A, Escalera B, Reillo A, J. Pharm. Sci., 87, 1590 (1998)
Ruidiaz MA, Delgado DR, Martinez F, Marcus Y, Fluid Phase Equilib., 299(2), 259 (2010)
Sotomayor RG, Holguin AR, Romdhani A, Martinez F, Jouyban A, J. Solution Chem., 42, 358 (2013)
Marcus Y, J. Mol. Liq., 140, 61 (2008)
Marcus Y, Acta Chim. Slov., 56, 40 (2009)
Marcus Y, Solvent Mixtures: Properties and Selective Solvation, Marcel Dekker, New York, 180 (2002).
Marcus Y, The Properties of Solvents, Wiley, Chichester, 145 (1998).
Henni A, Hromek JJ, Tontiwachwuthikul P, Chakma A, J. Chem. Eng. Data, 49(2), 231 (2004)
Fedors RF, Polym. Eng. Sci., 14, 147 (1974)
Delgado DR, Pena MA, Martinez F, J. Solution Chem., 43, 360 (2014)
Delgado DR, Almanza OA, Martinez F, Pena MA, Jouyban A, Acree WE, J. Chem. Thermodyn., 97, 264 (2016)
