Thermodynamics Research Center / ThermoML | Journal of Chemical Thermodynamics

The dissolution behavior and apparent thermodynamic analysis of temozolomide in pure and mixed solvents

Wu, Yuefang, Gao, Jiangwei, Yan, Suyue, Wu, Chenmeng, Hu, Bin
J. Chem. Thermodyn. 2019, 132, 54-61
ABSTRACT
In commonly used solvents, the dissolving capacity of temozolomide is limited. This work is to research the dissolution behavior in different polarity ranges. The solubility of temozolomide in methanol, ethanol, n-propanol, isopropanol, acetone, acetonitrile, N,N-dimethylformamide (DMF), ethyl acetate, dimethyl sulfoxide (DMSO), 1,4-dioxane and mixture of (DMF + ethanol) was experimentally determined at T = 293.15-333.15 K. The modified Apelblat equation, lambdah equation, Jouyban-Acree model and CNIBS/R-K model are applied to correlate the solubility. All the values of RAD and RMSD are no more than 3.43 * 10-2 and 2.86 * 10-4, respectively. Apparent thermodynamic analysis indicate that the dissolution is an endothermic, spontaneous and entropy driven process. More importantly, the change of temperature and the addition of co-solvent (DMF) can make the operation of crystallization purification more controllable.
Compounds
# Formula Name
1 C6H6N6O2 Temozolomide
2 C2H6O ethanol
3 C3H8O propan-2-ol
4 CH4O methanol
5 C3H8O propan-1-ol
6 C4H8O2 ethyl acetate
7 C2H3N acetonitrile
8 C4H8O2 1,4-dioxane
9 C3H6O acetone
10 C3H7NO dimethylformamide
11 C2H6OS dimethyl sulfoxide
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
  • 4
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 9
  • POMD
  • 1
  • 2
  • 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
  • 3
  • 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
  • 7
  • 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
  • 11
  • 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
  • 10
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 9
  • POMD
  • 1
  • 2
  • 10
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Solvent: Mass fraction - 10; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 72