Thermodynamics Research Center / ThermoML | Journal of Chemical Thermodynamics

Co-solvence phenomenon and thermodynamic properties of edaravone in pure and mixed solvents

Li, Rongrong, Yao, Lusha, Khan, Arshad, Zhao, Bo, Wang, Dehua, Zhao, Jia, Han, Deman
J. Chem. Thermodyn. 2019, 138, 304-312
ABSTRACT
The dissolution behavior of drugs in cosolvent mixtures is very important, especially in systems with co-solvence phenomenon. The solubility of edaravone in pure and mixed solvents was determined experimentally by using the isothermal dissolution equilibrium method within the temperature range from (273.15 to 313.15) K under atmosphere pressure (101.3 kPa). The maximum solubility was (4.72 * 10-2 in mole fraction) obtained at 313.15 K in n-propanol, and the minimum data was found at 273.15 K in acetonitrile. However, in mixed solvents, the solubility of edaravone increased with the increasing temperature, while increased with increasing co-solvent mass fraction (w) to a maximum value at w = 0.6 and then decreased, and Extended Hildebrand Solubility Approach was applied to explain this phenomenon. In addition, the solubility data obtained were correlated with the modified Apelblat equation, lambdah equation, Jouyban-Acree model and CNIBS/R-K model. The results indicated that the modified apelblat equation and Jouyban-Acree model are more suitable to correlate solubility data of edaravone in studied pure and mixed solvents, respectively. The apparent dissolution standard enthalpy (deltaHsolo), apparent molar standard Gibbs energy (deltaGsolo) and deltaSsolo of edaravone in pure and mixed solvents were also evaluated.
Compounds
# Formula Name
1 C10H10N2O Edaravone
2 C4H8O2 ethyl acetate
3 CH4O methanol
4 C2H6O ethanol
5 C3H8O propan-2-ol
6 C3H8O propan-1-ol
7 C7H8 toluene
8 C2H3N acetonitrile
9 C3H6O acetone
Datasets
The table above is generated from the ThermoML associated json file (link above). POMD and RXND refer to PureOrMixture and Reaction Datasets. The compound numbers are included in properties, variables, and phases, if specificied; the numbers refer to the table of compounds on the left.
Type Compound-# Property Variable Constraint Phase Method #Points
  • POMD
  • 1
  • Triple point temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 1
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 1
  • 2
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 9
  • POMD
  • 1
  • 2
  • 3
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Solvent: Mass fraction - 2; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 54
  • POMD
  • 1
  • 3
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 9
  • POMD
  • 1
  • 4
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 9
  • POMD
  • 1
  • 5
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 9
  • POMD
  • 1
  • 6
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 9
  • POMD
  • 1
  • 7
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 9
  • POMD
  • 1
  • 8
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 9
  • POMD
  • 1
  • 9
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 9
  • POMD
  • 1
  • 2
  • 4
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Solvent: Mass fraction - 2; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 54