Abstract
The solubilities of piroxicam in binary and ternary mixtures of polyethylene glycols 200 or 400 with ethanol and water (138 data points) at 298.2 K were determined and mathematically represented by cosolvency models. The solubilities were measured using the shake flask method and the models are used to fit the solubility data of piroxicam in the solvent mixtures. The overall mean relative deviations (OMRDs %) for fitting the solubility data of piroxicam in binary and ternary mixtures using the Williams–Amidon and Jouyban–Acree models are 30.7 and 26.8 %, respectively, and the OMRD % values for predicting the solubilities of piroxicam by the trained versions of the Jouyban–Acree model is 57.3 %.
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Zakeri-Milani, P., Barzegar-Jalali, M., Azimi, M., Valizadeh, H.: Biopharmaceutical classification of drugs using intrinsic dissolution rate (IDR) and rat intestinal permeability. Eur. J. Pharm. Biopharm. 73, 102–106 (2009)
Box, K.J., Comer, J.E.: Using measured pK a, log P and solubility to investigate supersaturation and predict BCS class. Curr. Drug Metab. 9, 869–878 (2008)
Leuner, C., Dressman, J.: Improving drug solubility for oral delivery using solid dispersions. Eur. J. Pharm. Biopharm. 50, 47–60 (2000)
Alsaidan, S.M., Alsughayer, A.A., Eshra, A.G.: Improved dissolution rate of indomethacin by adsorbents. Drug Dev. Ind. Pharm. 24, 389–394 (1998)
Balakrishnan, A., Rege, B.D., Amidon, G.L., Polli, J.E.: Surfactant-mediated dissolution: contributions of solubility enhancement and relatively low micelle diffusivity. J. Pharm. Sci. 93, 2064–2075 (2004)
Soltanpour, Sh, Jouyban, A.: Solubility of acetaminophen and ibuprofen in polyethylene glycol 600, propylene glycol and water mixtures at 25 °C. J. Mol. Liq. 155, 80–84 (2010)
Soltanpour, Sh, Jouyban, A.: Solubility of acetaminophen and ibuprofen in binary and ternary mixtures of polyethylene glycol 600, ethanol and water. Chem. Pharm. Bull. 58, 219–224 (2010)
Jouyban, A., Soltanpour, Sh., Acree, W.E. Jr.: Solubility of acetaminophen and ibuprofen in the mixtures of polyethylene glycol 200 or 400 with ethanol and water and the density of solute-free mixed solvents at 298.2 K. J. Chem. Eng. Data 55, 5252–5257 (2010)
Lee, B.J., Lee, J.R.: Enhancement of solubility and dissolution rate of poorly water-soluble naproxen by complexation with 2-hydroxypropyl-β-cyclodextrin. Arch. Pharm. Res. 18, 22–26 (1995)
Nokhodchi, A., Javadzadeh, Y., Siahi-Shadbad, M.R., Barzegar-Jalali, M.: The effect of type and concentration of vehicles on the dissolution rate of a poorly soluble drug (indomethacin) from liquisolid compacts. J. Pharm. Pharm. Sci. 8, 18–25 (2005)
Cavallari, C., Luppi, B., Di Pietra, A.M., Rodriguez, L., Fini, A.: Enhanced release of indomethacin from PVP/stearic acid microcapsules prepared coupling co-freeze-drying and ultrasound assisted spray-congealing process. Pharm. Res. 24, 521–529 (2007)
Valizadeh, H., Nokhodchi, A., Qarakhani, N., Zakeri-Milani, P., Azarmi, S., Hassanzadeh, D., Löbenberg, R.: Physicochemical characterization of solid dispersions of indomethacin with PEG 6000, Myrj 52, lactose, sorbitol, dextrin, and Eudragit® E100. Drug Dev. Ind. Pharm. 30, 303–317 (2004)
Preechagoon, D., Udomprateep, A., Manwiwattanagul, G.: Improved dissolution rate of poorly soluble drug by incorporation of buffers. Drug Dev. Ind. Pharm. 26, 891–894 (2000)
Bandi, N., Wei, W., Roberts, C.B., Kotra, L.P., Kompella, U.B.: Preparation of budesonide- and indomethacin-hydroxypropyl-beta-cyclodextrin (HPBCD) complexes using a single-step, organic-solvent-free supercritical fluid process. Eur. J. Pharm. Sci. 23, 159–168 (2004)
Jambhekar, S., Casella, R., Maher, T.: The physicochemical characteristics and bioavailability of indomethacin from β-cyclodextrin, hydroxyethyl-β-cyclodextrin, and hydroxypropyl-β-cyclodextrin complexes. Int. J. Pharmaceut. 270, 149–166 (2004)
Rahbari-Sisakht, M., Taghizadeh, M., Eliassi, A.: Densities and viscosities of binary mixtures of poly(ethylene glycol) and poly(propylene glycol) in water and ethanol in the 293.15–338.15 K temperature range. J. Chem. Eng. Data 48, 1221–1224 (2003)
Harris, J.M.: Poly(ethylene glycol) Chemistry, Biotechnical and Biomedical Applications. Plenum Predd, New York (1992)
Powell, G.M., Davidson, R.I. (eds.): Handbook of Water Soluble Gums and Resins. McGraw-Hill, New York (1980)
Jouyban, A.: Review of the cosolvency models for predicting solubility of drugs in water–cosolvent mixtures. J. Pharm. Pharm. Sci. 11, 32–58 (2008)
Yalkowsky, S.H., Roseman, T.: Solubilization of Drugs by Cosolvents. Marcel Dekker, New York (1981)
Valvani, S.C., Yalkowsky, S.H., Roseman, T.J.: Solubility and partitioning IV: aqueous solubility and octanol–water partition coefficients of liquid nonelectrolytes. J. Pharm. Sci. 70, 502–507 (1981)
Williams, N.A., Amidon, G.L.: Excess free energy approach to the estimation of solubility in mixed solvent system. II. Ethanol–water mixtures. J. Pharm. Sci. 73, 14–18 (1984)
Williams, N.A., Amidon, G.L.: Excess free energy approach to the estimation of solubility in mixed solvent systems. I: Theory. J. Pharmaceut. Sci. 73, 9–13 (1984)
Williams, N.A., Amidon, G.L.: Excess free energy approach to the estimation of solubility in mixed solvent systems. III: Ethanol–propylene glycol–water mixtures. J. Pharm. Sci. 73, 18–23 (1984)
Acree Jr, W.E.: 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 198, 71–79 (1992)
Jouyban-Gharamaleki, A., Valaee, L., Barzegar-Jalali, M., Clark, B.J., Acree Jr, W.E.: Comparison of various cosolvency models for calculating solute solubility in water–cosolvent mixtures. Int. J. Pharm. 171, 93–101 (1999)
Jouyban, A., Acree Jr, W.E.: In silico prediction of drug solubility in water–ethanol mixtures using Jouyban–Acree model. J. Pharm. Pharm. Sci. 9, 262–269 (2006)
Jouyban, A., Acree Jr, W.E.: Prediction of drug solubility in ethanol–ethyl acetate mixtures at various temperatures using the Jouyban–Acree model. J. Drug Deliv. Sci. Technol. 17, 159–160 (2007)
Jouyban-Gharamaleki, A., Acree Jr, W.E.: Comparison of models for describing multiple peaks in solubility profiles. Int. J. Pharm. 167, 177–182 (1998)
Jouyban, A., Shokri, J., Barzegar-Jalali, M., Hassanzadeh, D., Acree Jr, W.E., Ghafourian, T., Nokhodchi, A.: Solubility of chlordiazepoxide, diazepam, and lorazepam in ethanol + water mixtures at 303.2 K. J. Chem. Eng. Data 54, 2142–2145 (2009)
Jouyban, A., Fakhree, M.A.A., Mirzaei, Sh, Ghafourian, T., Soltanpour, Sh, Nokhodchi, A.: Solubility prediction of paracetamol in water–glycerol mixtures at 25 and 30 °C using the Jouyban–Acree model. Asian J. Chem. 21, 7249–7253 (2009)
Sardari, F., Jouyban, A.: Solubility of 3-ethyl-5-methyl-(4RS)-2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate monobenzenesulfonate (amlodipine besylate) in ethanol + water and propane-1,2-diol + water mixtures at various temperatures. J. Chem. Eng. Data 57, 2848–2854 (2012)
Eghrary, Sh, Zarghami, R., Martinez, F., Jouyban, A.: Solubility of 2-butyl-3-benzofuranyl 4-(2-(diethylamino)ethoxy)-3,5-diiodophenyl ketone hydrochloride (amiodarone HCl) in ethanol + water and N-methyl-2-pyrrolidone + water mixtures at various temperatures. J. Chem. Eng. Data 57, 1544–1550 (2012)
Moffat, A.C.: Clarke’s Analysis of Drug and Poisons. Pharmaceutical Press, London (2004)
Jouyban, A., Fakhree, M.A.A.: Experimental and computational methods pertaining to drug solubility. In: Acree Jr, W.E. (ed.) Toxicity and Drug Testing. InTech Publisher, New York (2012)
Jouyban, A., Soltanpour, Sh, Tamizi, E.: Solubility prediction of solutes in aqueous mixtures of ethylene glycols. Pharmazie 63, 548–550 (2008)
Li, A., Yalkowsky, S.H.: Predicting cosolvency. 1. Solubility ratio and solute log K ow. Ind. Eng. Chem. Res. 37, 4470–4475 (1998)
Jouyban, A.: Solubility prediction of drugs in water–polyethylene glycol 400 mixtures using Jouyban–Acree model. Chem. Pharm. Bull. 54, 1561–1566 (2006)
Shayanfar, A., Fakhree, M.A.A., Acree Jr, W.E., Jouyban, A.: Solubility of lamotrigine, diazepam, and clonazepam in ethanol + water mixtures at 298.15 K. J. Chem. Eng. Data 54, 1107–1109 (2009)
Jouyban, A., Soltanpour, Sh: Solubility of pioglitazone hydrochloride in binary and ternary mixtures of water, propylene glycol, and polyethylene glycols 200, 400 and 600 at 298.2 K. AAPS PharmSciTech. 11, 1713–1717 (2010)
Soltanpour, Sh, Jouyban, A.: Solubility of lamotrigine in binary and ternary mixtures of N-methyl pyrrolidone and water with polyethylene glycols 200, 400 and 600 at 298.2 K. J. Mol. Liq. 180, 1–6 (2013)
Soltanpour, S, Jouyban, A.: Solubility of acetaminophen and ibuprofen in binary and ternary mixtures of polyethylene glycols 200 and 400, propylene glycol and water at 25 °C. Chem. Eng. Commun. (2013) (in press)
Koleske, J.V.: Paint and Coating Testing Manual, 14th edn. In: Gardner-Sward Handbook, Chap 35. ASTM, Philadelphia (1995)
Amiran, J., Nicolosi, V., Bergin, S.D., Khan, O., Lyons, P.E., Coleman, J.N.: High quality dispersions of functionalized single walled nanotubes at high concentration. J. Phys. Chem. C 112, 3519–3524 (2008)
Jouyban, A.: Handbook of Solubility Data for Pharmaceuticals. CRC Press, Boca Raton (2009)
Acknowledgments
This paper is resulted from a Pharm. D. thesis with the proposal number of (A-11-387-7). The authors are grateful for financial support from Zanjan University of Medical Sciences, Iran.
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Soltanpour, S., Gharagozlu, A. Piroxicam Solubility in Binary and Ternary Solvents of Polyethylene Glycols 200 or 400 with Ethanol and Water at 298.2 K: Experimental Data Report and Modeling. J Solution Chem 44, 1407–1423 (2015). https://doi.org/10.1007/s10953-015-0353-x
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DOI: https://doi.org/10.1007/s10953-015-0353-x