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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

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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

  1. BP. Office of the British Pharmacopoeia Commission, London (1998)

  2. USP: 23rd Revision. US Pharmacopeial Convention, Rockville (1995)

    Google Scholar 

  3. 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)

    Google Scholar 

  4. Dressman, J., Reppas, C.: Drug solubility: how to measure it, how to improve it. Adv. Drug Deliv. Rev. 59, 531–532 (2007)

    Article  CAS  Google Scholar 

  5. 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)

    Article  CAS  Google Scholar 

  6. 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)

    Article  CAS  Google Scholar 

  7. Harris, J.M.: Poly(ethylene glycol) Chemistry, Biotechnical and Biomedical Applications. Plenum, New York (1992)

    Google Scholar 

  8. Powell, G.M., Davidson, R.I. (eds.): Handbook of Water Soluble Gums and Resins. McGraw-Hill, New York (1980)

    Google Scholar 

  9. Strickley, A.: Solubilizing excipients in oral and injectable formulations. Pharm. Res. 21, 201–229 (2004)

    Article  CAS  Google Scholar 

  10. 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)

    Article  CAS  Google Scholar 

  11. 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)

    Article  Google Scholar 

  12. 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)

    Article  CAS  Google Scholar 

  13. Pirhonen, E., Nieuwenhuis, J., Kaikkonen, A., Nieminen, T., Weber, F.: Resorbable polymer compositions, implant and method of making implant. Patent No.: 6926903, 2005

  14. 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

  15. Komer, G.: Avermectin formulation. Patent No. 5773422, 1998

  16. Dornhofer, W., Embrechts, E.: Injection solution for intramuscular and subcutaneous administration to animal. Patent No. 5753636, 1998

  17. Jouyban, A.: Review of the cosolvency models for predicting solubility of drugs in water-cosolvent mixture. J. Pharm. Pharm. Sci. 11, 32–58 (2008)

    CAS  Google Scholar 

  18. 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)

    Article  CAS  Google Scholar 

  19. 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)

    Article  Google Scholar 

  20. 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)

    CAS  Google Scholar 

  21. 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)

    CAS  Google Scholar 

  22. 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)

    Article  CAS  Google Scholar 

  23. Jouyban-Gharamaleki, A., Acree Jr, W.E.: Comparison of models for describing multiple peaks in solubility profiles. Int. J. Pharm. 167, 177–182 (1998)

    Article  CAS  Google Scholar 

  24. 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)

    Article  CAS  Google Scholar 

  25. 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)

    CAS  Google Scholar 

  26. 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)

    Article  CAS  Google Scholar 

  27. 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)

    Article  CAS  Google Scholar 

  28. Moffat, A.C.: Clarke’s Analysis of Drug and Poisons. Pharmaceutical Press, London (2004)

    Google Scholar 

  29. 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)

    Google Scholar 

  30. Jouyban, A.: Solubility prediction of drugs in water–polyethylene glycol 400 mixtures using Jouyban–Acree model. Chem. Pharm. Bull. 54, 1561–1566 (2006)

    Article  CAS  Google Scholar 

  31. 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)

    Article  CAS  Google Scholar 

  32. 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)

    Article  Google Scholar 

  33. 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)

    Article  CAS  Google Scholar 

  34. 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)

    Article  CAS  Google Scholar 

  35. Hill, L.W.: Paint and coating testing manual. In: Koleske, J.V. (ed.) Gardner–Sward Handbook, 14th edn. ASTM, Philadelphia, PA (1995)

    Google Scholar 

  36. 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)

    Article  CAS  Google Scholar 

  37. 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)

    Google Scholar 

  38. Jouyban, A.: Handbook of Solubility Data for Pharmaceuticals. CRC Press, Boca Raton (2009)

    Book  Google Scholar 

  39. 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)

    Article  CAS  Google Scholar 

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Acknowledgments

The authors are grateful for financial support from Zanjan University of Medical Sciences, Iran (No. A-11-387-1).

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Correspondence to Shahla Soltanpour.

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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

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