Abstract
Experimental solubilities of diazepam in binary and ternary solvents of polyethylene glycols 200 and 400 with N-methyl pyrrolidone and water at T = 298.2 K are reported. The Jouyban–Acree model was used to fit solubility data of diazepam in the binary and ternary solvent mixtures (106 data points) in which the overall mean relative deviations (OMRD %) is 13.1 % and the prediction OMRD % is 31.7 %. The combined version of the Jouyban–Acree model with Hansen solubility parameters was used for fitting and predicting the solubility data and the OMRDs % are 10.0 and 20.8 %, respectively. Also, the previously proposed trained versions of the Jouyban–Acree model were used for predicting the reported data in this work and all results are listed in the tables. The density of the solute-free solvent mixtures were measured and employed to calculate the constants of the Jouyban–Acree model and then the densities of the saturated solutions were predicted.
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References
BP. Office of the British Pharmacopoeia Commission, London (1998)
USP: 23rd Revision. US Pharmacopeial Convention, Rockville (1995)
Serajuddin, A.T.M., Pudipeddi, M.: Salt selection strategies. In: Stahl, P.H., Wermuth, C.G. (eds.) Handbook of Pharmaceutical Salts: Properties, Selection and Use, pp. 135–160. Wiley-VCH, Weinheim (2002)
Dressman, J., Reppas, C.: Drug solubility: how to measure it, how to improve it. Adv. Drug Deliv. Rev. 59, 531–532 (2007)
Blagden, N., de Matas, M., Gavan, P.T., York, P.: Crystal engineering of active pharmaceutical ingredients to improve solubility and dissolution rates. Adv. Drug Deliv. Rev. 59, 617–630 (2007)
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, New York (1992)
Powell, G.M., Davidson, R.I. (eds.): Handbook of Water Soluble Gums and Resins. McGraw-Hill, New York (1980)
Strickley, A.: Solubilizing excipients in oral and injectable formulations. Pharm. Res. 21, 201–229 (2004)
Uch, A.S., Hesse, U., Dressman, J.B.: Use of 1-methyl-pyrrolidone as a solubilizing agent for determining the uptake of poorly soluble drugs. Pharm. Res. 16, 968–971 (1999)
Ishihara, T., Goto, M., Kanazawa, H., Higaki, M., Mizushima, Y.: Efficient entrapment of poorly water-soluble pharmaceuticals in hybrid nanoparticles. J. Pharm. Sci. 98, 2357–2363 (2008)
Koizumi, A., Makiko, F., Kondoh, M., Watanabe, Y.: Effect of N-methyl pyrrolidone on skin permeation of estradiol. Eur. J. Pharm. Biopharm. 57, 473–847 (2004)
Pirhonen, E., Nieuwenhuis, J., Kaikkonen, A., Nieminen, T., Weber, F.: Resorbable polymer compositions, implant and method of making implant. Patent No.: 6926903, 2005
Malook, S.U., Boon, P.F.G., Morgan, J.P.: Method of reducing the swelling or pain associated with antibiotics compositions. Patent No. 4772460, 1988
Komer, G.: Avermectin formulation. Patent No. 5773422, 1998
Dornhofer, W., Embrechts, E.: Injection solution for intramuscular and subcutaneous administration to animal. Patent No. 5753636, 1998
Jouyban, A.: Review of the cosolvency models for predicting solubility of drugs in water-cosolvent mixture. J. Pharm. Pharm. Sci. 11, 32–58 (2008)
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, A., Soltanpour, Sh., Acree Jr, W.E.: Solubility of acetaminophen and ibuprofen in the mixtures of polyethylene glycol 200 or 400 with ethanol, and water, and density of solute free mixed solvents at 298.2 K. J. Chem. Eng. Data 55, 5252–5257 (2010)
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, New York (2012)
Jouyban, A.: Solubility prediction of drugs in water–polyethylene glycol 400 mixtures using Jouyban–Acree model. Chem. Pharm. Bull. 54, 1561–1566 (2006)
Soltanpour, Sh., Jouyban, A.: Solubility of acetaminophen and ibuprofen in polyethylene glycol 600, N-methyl pyrrolidone and water mixtures. J. Solution Chem. 40, 2032–2045 (2011)
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, 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)
Hill, L.W.: Paint and coating testing manual. In: Koleske, J.V. (ed.) Gardner–Sward Handbook, 14th edn. ASTM, Philadelphia, PA (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., Fathi-Azarbayjani, A., Khoubnasabjafari, M., Acree Jr, W.E.: Mathematical representation of the density of liquid mixtures at various temperatures using Jouyban–Acree model. Indian J. Chem. 44, 1553–1560 (2005)
Jouyban, A.: Handbook of Solubility Data for Pharmaceuticals. CRC Press, Boca Raton (2009)
Shayanfar, A., Acree Jr, W.E., Jouyban, A.: Solubility of clonazepam, diazepam, lamotrigine, and phenobarbital in N-methyl-2-pyrrolidone + water mixtures at 298.2 K. J. Chem. Eng. Data 54, 2964–2966 (2009)
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The authors are grateful for financial support from Zanjan University of Medical Sciences, Iran (No. A-11-387-1).
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Soltanpour, S., Panahi-Azar, V., Taheri, A. et al. Solubility Data of Diazepam in Binary and Ternary Mixtures of PEGs 200 and 400 with N-Methyl Pyrrolidone and Water at 298.2 K: Experimental Data and Modeling. J Solution Chem 42, 2281–2295 (2013). https://doi.org/10.1007/s10953-013-0106-7
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DOI: https://doi.org/10.1007/s10953-013-0106-7