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Solubility and Dissolution Thermodynamics of Cefmetazole Acid in Four Neat Solvents and Preferential Solvation in Co-Solvent Mixtures of (Methanol, Ethanol or Isopropanol) + Water

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Abstract

The solubilities of cefmetazole acid in methanol, ethanol, isopropanol and water were determined experimentally by using the saturation shake-flask method within the temperature range from (278.15 to 303.15) K under pressure p = 101.1 kPa. At a fixed temperature, the cefmetazole acid solubility falls in the order methanol > ethanol > isopropanol > water. The apparent dissolution enthalpy, dissolution entropy and Gibbs energy change were calculated. The acquired solubilities were correlated with Apelblat’s equation. The largest value of relative average deviation for mole fraction solubility was 0.45 × 10−2, and of root-mean-square deviation, 0.747 × 10−5. The type and extent and direction of solute–solvent interactions were identified using the concept of Linear Solvation Energy Relationship. In addition, the preferential solvation parameters (δx1,3) of cefmetazole acid in co-solvent mixtures of methanol (1) + water (2), ethanol (1) + water (2) and isopropanol (1) + water (2) were derived via the inverse Kirkwood–Buff integrals method. At 298.15 K, the magnitude of preferential solvation of cefmetazole acid by the co-solvent is highest in methanol mixtures, followed by ethanol mixtures, and finally by isopropanol mixtures.

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References

  1. Wang, L., Yan, Z., Shi, L.: Cefmetazole acid composition comprises cefmetazole acid and arginine aseptic powder dissolved in water at specified weight ratio. CN Patent 101,548,977 (October 07, 2009)

  2. Wang, L., Yang, L.: Antibacterial composition useful for preparing injection or powder injection, comprises Cefmetazole acid and sodium citrate. CN Patent 101,695,493 (April 21, 2010)

  3. Sun, M.M., Li, K.L., Du, S.C., Liu, Y.M., Han, D.D., Li, X.N., Yang, P., Liu, S.Y., Gong, J.B.: Correlation and thermodynamic analysis of solubility of cefmetazole acid in three (alcohol + water) binary solvents at temperatures from 278.15 K to 303.15 K. J. Chem. Thermodyn. 103, 355–365 (2016)

    Article  CAS  Google Scholar 

  4. Jouyban, A.: Review of the cosolvency models for predicting solubility of drugs in water–cosolvent mixtures. J. Pharm. Pharm. Sci. 11, 32–38 (2008)

    Article  CAS  PubMed  Google Scholar 

  5. Jouyban, A.: Handbook of Solubility Data for Pharmaceuticals. FL, CRC Press, Boca Raton (2010)

    Google Scholar 

  6. Rubino, J.T.: Cosolvents and cosolvency. In: Swarbrick, J., Boylan, J.C. (eds.) Encyclopedia of Pharmaceutical Technology. Marcel Dekker, Inc., New York (1988)

  7. Aulton, M.E.: Pharmaceutics. The Science of Dosage Forms Design. Second edn. Churchill Livingstone, London (2002)

    Google Scholar 

  8. Avdeef, A.: Absorption and drug development, solubility. In: Permeability and Charge State. Wiley-Interscience, Hoboken (2003)

  9. Yalkowsky, S.H.: Solubility and Solubilization in Aqueous Media, pp. 180–235. American Chemical Society and Oxford University Press, New York (1999)

    Google Scholar 

  10. Marcus, Y.: Solvent Mixtures: Properties and Selective Solvation. Marcel Dekker Inc, New York, NY (2002)

    Google Scholar 

  11. Marcus, Y.: Preferential solvation in mixed solvents. In: Smith, P.E., Matteoli E., O’Connell J.P. (eds.) Fluctuation Theory of Solutions: Applications in Chemistry, Chemical Engineering, and Biophysics. CRC Press, Boca Raton (2013)

  12. Tooski, H.F., Jabbaril, M., Farajtabar, A.: Solubility and preferential solvation of the flavonoid naringenin in some aqueous/organic solvent mixtures. J. Solution Chem. 45, 1701–1714 (2016)

    Article  CAS  Google Scholar 

  13. Delgado, D.R., Martínez, F.: Preferential solvation of sulfadiazine, sulfamerazine and sulfamethazine in ethanol + water solvent mixtures according to the IKBI method. J. Mol. Liq. 193, 152–159 (2014)

    Article  CAS  Google Scholar 

  14. Cárdenas, Z.J., Jiménez, D.M., Delgado, D.R., Almanza, O.A., Jouyban, A., Martínez, F., Acree Jr., W.E.: Solubility and preferential solvation of some n-alkyl-parabens in methanol + water mixtures at 298.15 K. J. Chem. Thermodyn. 108, 26–37 (2017)

    Article  CAS  Google Scholar 

  15. Chen, G.Q., Chen, J., Cheng, C., Cong, Y., Du, C.B., Zhao, H.K.: Solubility and preferential solvation of econazole nitrate in binary solvent mixtures of methanol, ethanol and 1,4-dioxane in water. J. Chem. Thermodyn. 111, 228–237 (2017)

    Article  CAS  Google Scholar 

  16. Li, X.B., Cheng, C., Cong, Y., Du, C.B., Zhao, H.K.: Preferential solvation of pioglitazone hydrochloride in some binary co-solvent mixtures according to the inverse Kirkwood-Buff integrals method. J. Chem. Thermodyn. 110, 218–226 (2017)

    Article  CAS  Google Scholar 

  17. Jabbari, M., Khosravi, N., Feizabadi, M., Ajloo, D.: Solubility temperature and solvent dependence and preferential solvation of citrus flavonoid naringin in aqueous DMSO mixtures: an experimental and molecular dynamics simulation study. RSC Adv. 7, 14776–14789 (2017)

    Article  CAS  Google Scholar 

  18. Cárdenas, Z.J., Almanza, O.A., Jouyban, A., Martínez, F., Acree Jr., W.E.: Solubility and preferential solvation of phenacetin in methanol + water mixtures at 298.15 K. Phys. Chem. Liq. 197, 1–17 (2016)

    Google Scholar 

  19. Delgado, D.R., Peña, M.Á., Martínez, F., Jouyban, A., Acree Jr., W.E.: Further numerical analyses on the solubility of sulfapyridine in ethanol + water mixtures. Pharm. Sci. 22, 143–152 (2016)

    Article  Google Scholar 

  20. Martínez, F., Jouyban, A., Acree Jr., W.E.: Solubility of phenobarbital in aqueous cosolvent mixtures revisited: IKBI preferential solvation analysis. Phys. Chem. Liq. 55, 432–443 (2016)

    Article  CAS  Google Scholar 

  21. Jouyban, A., Fakhree, M.A.: Experimental, computational methods pertaining to drug solubility. In: Acree Jr., W.E. (ed.) Toxicity and Drug Testing, pp. 187–218. InTech. Rijeka, Croatia (2012)

    Google Scholar 

  22. Jouyban, A., Martinez, F., Panahi-Azar, V.: Solubility of fluphenazine decanoate in aqueous mixtures of polyethylene glycols 400 and 600 at various temperatures. Fluid Phase Equilib. 368, 58–64 (2014)

    Article  CAS  Google Scholar 

  23. Higuchi, T., Connors, K.A.: Phase-solubility techniques. Adv. Anal. Chem. Instrum. 4, 117–122 (1965)

    CAS  Google Scholar 

  24. Chen, B., Chen, Z.Q.: Cefmetazole crystal form, preparation method thereof, and pharmaceutical composition containing cefmetazole. CN Patent 104,370,942 (Feb 25, 2015)

  25. Apelblat, A., Manzurola, E.: Solubilities of l-glutamic acid, 3-nitrobenzoic acid, p-toluic acid, calcium-l-lactate, calcium gluconate, magnesium-DL-aspartate, and magnesium-L-lactate in water. J. Chem. Thermodyn. 34, 1127–1136 (2002)

    Article  CAS  Google Scholar 

  26. Apelblat, A., Manzurola, E.: Solubilities of l-aspartic, dl-aspartic, dl-glutamic, p-hydroxybenzoic, o-anistic, p-anisic, and itaconic acids in water from T = 278 K to T = 345 K. J. Chem. Thermodyn. 29, 1527–1533 (1997)

    Article  CAS  Google Scholar 

  27. Taft, R.W., Abboud, J.-L.M., Kamlet, M.I., Abraham, M.H.: Linear solvation energy relations. J. Solution Chem. 14, 153–186 (1985)

    Article  CAS  Google Scholar 

  28. Marcus, Y.: The properties of organic liquids that are relevant to their use as solvating solvents. Chem. Soc. Rev. 22, 409–416 (1993)

    Article  CAS  Google Scholar 

  29. Farajtabar, A., Gharib, F.: Spectral analysis of naringenin deprotonation in aqueous ethanol solutions. Chem. Pap. 67, 538–545 (2013)

    Article  CAS  Google Scholar 

  30. Naderi, F., Farajtabar, A., Gharib, F.: Solvatochromic and preferential solvation of fluorescein in some water–alcoholic mixed solvents. J. Mol. Liq. 190, 126–132 (2014)

    Article  CAS  Google Scholar 

  31. Milkhail, S.Z., Kimel, W.R.: Densities and viscosities of methanol–water mixtures. J. Chem. Eng. Data 6, 533–537 (1961)

    Article  Google Scholar 

  32. Aliaj, F., Syla, N., Bytyqi-Damoni, A.: Refractive indices, densities and excess molar volumes of binary systems methanol + water and ethanol + water at T = 293.15 K. AKTET. J. Inst. Alb-Shkenca 9, 36–42 (2006)

  33. Khattab, I.S., Bandarkar, F., Fakhree, M.A.A., Jouyban, A.: Density, viscosity, and surface tension of water + ethanol mixtures from 293 to 323 K. Korean J. Chem. Eng. 29, 812–817 (2012)

    Article  CAS  Google Scholar 

  34. Pang, F.M., Seng, C.E., Teng, T.T., Ibrahim, M.H.: Densities and viscosities of aqueous solutions of 1-propanol and 2-propanol at temperatures from 293.15 K to 333.15 K. J. Mol. Liq. 136, 71–78 (2007)

    Article  CAS  Google Scholar 

  35. Marcus, Y.: The Properties of Solvents. John Wiley & Sons, Chichester (1998)

    Google Scholar 

  36. Ben-Naim, A.: Theory of preferential solvation of nonelectrolytes. Cell Biophys. 12, 255–269 (1988)

    Article  CAS  PubMed  Google Scholar 

  37. Ben-Naim, A.: Preferential solvation in two- and in three-component systems. Pure Appl. Chem. 62, 25–34 (1990)

    Article  CAS  Google Scholar 

  38. Marcus, Y.: Solubility and solvation in mixed solvent systems. Pure Appl. Chem. 62, 2069–2076 (1990)

    Article  CAS  Google Scholar 

  39. Kamlet, M.J., Taft, R.W.: The solvatochromic comparison method. I. The beta-scale of solvent hydrogen-bond acceptor (HBA) basicities. J. Am. Chem. Soc. 98, 377–383 (1976)

    Article  CAS  Google Scholar 

  40. Taft, R.W., Kamlet, M.J.: The solvatochromic comparison method. II. The alpha-scale of solvent hydrogen-bond donor (HBD) acidities. J. Am. Chem. Soc. 98, 2886–2894 (1976)

    Article  CAS  Google Scholar 

  41. Zhang, C.L., Zhao, F., Wang, Y.: Thermodynamics of the solubility of sulfamethazine in methanol, ethanol, 1-propanol, acetone, and chloroform from 293.15 to 333.15 K. J. Mol. Liq. 159, 170–172 (2011)

    Article  CAS  Google Scholar 

  42. Cristancho, D.M., Martínez, F.: Solubility and preferential solvation of meloxicam in ethyl acetate + ethanol mixtures at several temperatures. J. Mol. Liq. 200, 122–128 (2014)

    Article  CAS  Google Scholar 

  43. Perlovich, G.L., Kurkov, S.V., Kinchin, A.N., Bauer-Brandl, A.: Thermodynamics of solutions III: comparison of the solvation of (+)-naproxen with other NSAIDs. Eur. J. Pharm. Biopharm. 57, 411–420 (2004)

    Article  CAS  PubMed  Google Scholar 

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Acknowledgements

This work was supported by the Science and Technology Research Key Project of the Education Department of Henan Province (Project number: SJCX17_0621). The authors would like to express their gratitude for the Priority Academic Program Development of Jiangsu Higher Education Institutions.

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Authors and Affiliations

  1. Changzhou Vocational Institute of Engineering, School of Pharmaceutical and Environmental Engineering, Jiangsu, 213164, Changzhou, People’s Republic of China

    Qiong He

  2. College of Chemistry and Chemical Engineering, YangZhou University, Yangzhou, 225002, Jiangsu, People’s Republic of China

    Min Zheng & Hongkun Zhao

  3. Department of Chemistry, Jouybar Branch, Islamic Azad University, Jouybar, Iran

    Ali Farajtabar

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  1. Qiong He
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Correspondence to Hongkun Zhao.

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He, Q., Zheng, M., Farajtabar, A. et al. Solubility and Dissolution Thermodynamics of Cefmetazole Acid in Four Neat Solvents and Preferential Solvation in Co-Solvent Mixtures of (Methanol, Ethanol or Isopropanol) + Water. J Solution Chem 47, 838–854 (2018). https://doi.org/10.1007/s10953-018-0758-4

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