Preferential solvation of etoricoxib in some aqueous binary cosolvent mixtures at 298.15 K

Abstract

Preferential solvation parameters of etoricoxib in several aqueous cosolvent mixtures were calculated from solubilities and other thermodynamic properties by using the IKBI method. Cosolvents studied were as follows: 1,4-dioxane, N,N-dimethylacetamide, 1,4-butanediol, N,Ndimethylformamide, ethanol and dimethyl sulfoxide. Etoricoxib exhibits solvation effects, being the preferential solvation parameter δx 1,3 , negative in water-rich and cosolvent-rich mixtures but positive in mixtures with similar proportions of both solvents. It is conjecturable that the hydrophobic hydration in water-rich mixtures plays a relevant role in drug solvation. In mixtures of similar solvent proportions where etoricoxib is preferentially solvated by the cosolvents, the drug could be acting as Lewis acid with the more basic cosolvents. Finally, in cosolvent-rich mixtures the preferential solvation by water could be due to the more acidic behaviour of water. Nevertheless, the specific solutesolvent interactions in the different binary systems remain unclear because no relation between preferential solvation magnitude and cosolvent polarities has been observed.

Solubility Determination, Modeling, and Preferential Solvation of 1-(2-Bromophenyl)-pyrrole-2,5-dione in Aqueous Binary Mixtures of Isopropanol, Ethanol, N-Methyl-2-pyrrolidinone and Methanol

“…Preferential solvation may give rise to the difference between the bulk solvent composition and shell solvent composition nearby the solute, rather than a particular atom of the solute. The inverse Kirkwood−Buff integrals (abbreviated as IKBIs, eq 21) defines the local compositions of a specific solvent nearby the solute compared with the overall solution compositions: [6][7][8][9][10][11][12]27,41,42…”

“…where r refers to the distance between the centers of solute The preferential solvation parameter, δx 1,3 , of 1-(2bromophenyl)-pyrrole-2,5-dione (3) by isopropanol, ethanol, NMP, or methanol (1) in aqueous solutions can be described as [6][7][8][9][10][11][12]27,41,42 x x x x…”

“…δx 1,3 can be accessible from the method of IKBIs for the cosolvent compositions. [6][7][8][9][10][11][12]27,41,42…”

Preferential Solvation of Drugs in Binary Solvent Mixtures

“…Preferential solvation parameters of etoricoxib in several aqueous co-solvent mixtures, involving 1,4-dioxane, N,N-dimethylacetamide, 1,4-butanediol, N,N-dimethylformamide, ethanol and dimethyl sulfoxide (solvent A), were calculated from solubilities and other thermodynamic data by the IKBI method [39]. Etoricoxib was preferentially solvated by water in water-rich and co-solvent-rich mixtures, δxS,A<0, but in mixtures with similar proportions of both solvents δxS,A>0 was found.…”

Further calculations on solubility of 2-chloro-3-(trifluoromethyl)pyridine in ethanol + 1-propanol solvent mixtures at various temperatures

“…values are lower than 1.0 x -2 and therefore, they could be attributed to uncertainties propagation rather than solvation effects [24,25]. On the other hand, in the interval 0.55 < o mixtures [26][27][28][29][30][31][32][33] and also in binary mixtures of organic solvents [34,35], where x1,3 values higher than 1.0 x 10 -2 have been reported and therefore, preferential solvation by the mixtures components on the solutes have been discussed in terms of solute-solvents interactions.…”