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Solubility Measurement and Thermodynamic Properties of Levetiracetam in Pure and Mixed Solvents

  • Shasha Li*
    Shasha Li
    School of Chemistry and Chemical Engineering and Institute of Fine Chemical Products, Suzhou University, Suzhou, Anhui 234000, People’s Republic of China
    *Tel.: + 86 05572871072. E-mail: [email protected]
    More by Shasha Li
  • Yong Liu
    Yong Liu
    School of Chemistry and Chemical Engineering and Institute of Fine Chemical Products, Suzhou University, Suzhou, Anhui 234000, People’s Republic of China
    More by Yong Liu
  • Fan Yin
    Fan Yin
    School of Chemistry and Chemical Engineering and Institute of Fine Chemical Products, Suzhou University, Suzhou, Anhui 234000, People’s Republic of China
    More by Fan Yin
  • , and 
  • Xiangli Ye
    Xiangli Ye
    School of Chemistry and Chemical Engineering and Institute of Fine Chemical Products, Suzhou University, Suzhou, Anhui 234000, People’s Republic of China
    More by Xiangli Ye
Cite this: J. Chem. Eng. Data 2018, 63, 12, 4669–4681
Publication Date (Web):November 20, 2018
https://doi.org/10.1021/acs.jced.8b00720
Copyright © 2018 American Chemical Society

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    Abstract

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    In this work, the solid–liquid equilibrium for levetiracetam in 10 neat solvents (methanol, ethanol, n-propanol, isopropanol, acetone, acetonitrile, ethyl acetate, 1,4-dioxane, toluene, and cyclohexane) and binary liquid mixtures (ethanol + ethyl acetate) was measured by using a static gravimetric method at temperatures T = 283.15–323.15 K under pressure of 101.2 kPa. In general, the equilibrium solubility was highest in methanol and lowest in cyclohexane. The modified Apelblat equation, λh equation, Wilson model, and NRTL model were used to correlate the solubility data in monosolvents; and the Jouyban–Acree model, van’t Hoff–Jouyban–Acree model, and Apelblat–Jouyban–Acree model were used to correlate the experiment data in the binary solvent mixtures. Compared with the results of the above models, the calculated solubility provided good results with the experimental data. Consequently, for the monosolvents, the values of root-mean-square deviation and relative average deviation were not exceeding 9.91 × 10–4 and 2.50%, respectively; and for the binary solvent mixtures, 2.75 × 10–4 and 0.80%. Furthermore, the thermodynamic properties of levetiracetam in monosolvents were calculated. From the analysis results, the dissolution process of levetiracetam was an endothermic, spontaneous, and entropy driven process. It is crucially important to understand the solubility and thermodynamic properties of levetiracetam in drug development. In particular, purification, recrystallization, and formulation development of levetiracetam in industry were effected by its solubility values.

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    Cited By

    This article is cited by 5 publications.

    1. Thitapond Nulek, Rachan Klaysri, Ruel Cedeno, Phattananawee Nalaoh, Sareeya Bureekaew, Vinich Promarak, Adrian E. Flood. Separation of Etiracetam Enantiomers Using Enantiospecific Cocrystallization with 2-Chloromandelic Acid. ACS Omega 2022, 7 (23) , 19465-19473. https://doi.org/10.1021/acsomega.2c01165
    2. Shasha Li, Xiaqing Nie, Chao Liu, Danhong Zhou. Solid–Liquid Phase Equilibrium and the Thermodynamic Correlation of Felodipine Form I in Pure and Mixed Solvents. Journal of Chemical & Engineering Data 2022, 67 (2) , 484-490. https://doi.org/10.1021/acs.jced.1c00566
    3. Pavan B. Rathi, Mayura Kale, Abolghasem Jouyban. Thermodynamic Modeling and Solubility Study of Satranidazole in Different Monosolvents at Different Temperatures. Journal of Chemical & Engineering Data 2021, 66 (10) , 3745-3756. https://doi.org/10.1021/acs.jced.1c00385
    4. Kalyani Kodide, Prashanth Asadi, Jyothi Thati. Solubility and Thermodynamic Modeling of Sulfanilamide in 12 Mono Solvents and 4 Binary Solvent Mixtures from 278.15 to 318.15 K. Journal of Chemical & Engineering Data 2019, 64 (12) , 5196-5209. https://doi.org/10.1021/acs.jced.9b00411
    5. Hemayat Shekaari, Masomeh Mokhtarpour, Fereshteh Mokhtarpour, Saeid Faraji, Fleming Martinez, Mohammed Taghi Zafarani-Moattar. Significant Increase in the Solubility of Celecoxib in Presence of Some Deep Eutectic Solvents as Novel Sustainable Solvents and the Thermodynamic Analysis of These Systems. Pharmaceutical Sciences 2020, 26 (4) , 423-433. https://doi.org/10.34172/PS.2020.48

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