Towards an Understanding of the Molecular Mechanism of Solvation of Drug Molecules: A Thermodynamic Approach by Crystal Lattice Energy, Sublimation, and Solubility Exemplified by Hydroxybenzoic Acids

Perlovich, German L.; Volkova, Тatyana V.; Bauer‐Brandl, Annette

doi:10.1002/jps.20611

Cited by 28 publications

(38 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The present work is a continuation of previous studies on thermodynamics of solvation of drug molecules (1)(2)(3)(4)(5)(6). Here, 2-acetaminophen and 3-acetaminophen molecules ( Fig.…”

Section: Introductionmentioning

confidence: 57%

Influence of Position and Size of Substituents on the Mechanism of Partitioning: A Thermodynamic Study on Acetaminophens, Hydroxybenzoic Acids, and Parabens

et al. 2008

Self Cite

View full text Add to dashboard Cite

Abstract. The objective of the present investigation was to study the influence of size, nature, and topology of substituents on the thermodynamic characteristics of sublimation, fusion, solubility, solvation, and partitioning processes of some drug and druglike molecules. Thermodynamic functions of sublimation process 2-acetaminophen and 3-acetaminophen were obtained on the basis of temperature dependencies of vapor pressure by the transpiration method. Thermodynamic characteristics of solubility processes in water, n-octanol, and n-hexane were calculated from the temperature dependencies of solubility using the solubility saturation method. For evaluation of fusion parameters, differential scanning calorimetry was used. A new approach to distinguishing specific and nonspecific energetic terms in the crystal lattice was developed. Specific and nonspecific solvation terms were distinguished using the transfer from the "inert" n-hexane to the other solvents. For the acetaminophen compounds and for some related drug molecules, the correlation between melting points and a parameter describing the ratio between specific and nonspecific interaction in the crystal lattices was obtained. A diagram enabling analysis of the mechanism of the partitioning process was applied. It was found that for isomers of benzoic acids and for acetaminophens, the position of substituents affects the mechanism of the partitioning process but not the extent of partitioning ($G 0 tr values). In contrast to this, an increased size of substituents (parabens) leads to essential changes in $G 0 tr values, but the mechanism of the partitioning process stays the same.

show abstract

“…The present work is a continuation of previous studies on thermodynamics of solvation of drug molecules (1)(2)(3)(4)(5)(6). Here, 2-acetaminophen and 3-acetaminophen molecules ( Fig.…”

Section: Introductionmentioning

confidence: 57%

Influence of Position and Size of Substituents on the Mechanism of Partitioning: A Thermodynamic Study on Acetaminophens, Hydroxybenzoic Acids, and Parabens

et al. 2008

Self Cite

View full text Add to dashboard Cite

show abstract

“…noted that solubility and dissolution rate are governed by additional factors other than crystal lattice energy (Perlovich et al, 2007a;Perlovich et al, 2007b;Perlovich et al, 2006).…”

Section: Accepted Manuscriptmentioning

confidence: 98%

Phospholipid-based solid drug formulations for oral bioavailability enhancement: A meta-analysis

Fong

Brandl

Bauer‐Brandl

2015

European Journal of Pharmaceutical Sciences

Self Cite

View full text Add to dashboard Cite

“…Entropy and Gibbs free energy of sublimation at 298 K and the deviation when these values are compared with literature [27][28][29]. (Error = 100 Á (property this work.…”

Section: Tablementioning

confidence: 98%

“…Table 2 shows the properties of the studied solids whereas table 3 shows the values of the sublimation enthalpies given by [27][28][29] and the values obtained with the proposed methodology. In table 3, it is possible to observe how the deviation in the DH sub is low when the values are compared with literature data (an average value between 8% and 9%).…”

Section: Validation Of the P Submentioning

confidence: 99%

“…The equations to treat the relative contributions have been used previously [27][28][29], and are used to identify the dominant effect on molecular organization changes in the structure. On the other hand, DG T sub , DS T sub , DH T sub are Gibbs free energy, entropy and enthalpy of sublimation at a given temperature T. Table 8 shows the values of the entropy (DS sub ) and Gibbs free energy of sublimation (DG sub ) at 298 K for the solids studied previously and the respective deviations from the results found in literature [27][28][29]. It can be observed that the average error in the Gibbs free energy is near 16% whereas with entropy this error is near 6%.…”

Section: Calculating More Solid Sublimation Properties and Acetaminopmentioning

confidence: 99%

See 1 more Smart Citation

On the use of semiempirical models of (solid+supercritical fluid) systems to determine solid sublimation properties

Valle

Galán

2011

The Journal of Chemical Thermodynamics

View full text Add to dashboard Cite

Towards an Understanding of the Molecular Mechanism of Solvation of Drug Molecules: A Thermodynamic Approach by Crystal Lattice Energy, Sublimation, and Solubility Exemplified by Hydroxybenzoic Acids

Cited by 28 publications

References 25 publications

Influence of Position and Size of Substituents on the Mechanism of Partitioning: A Thermodynamic Study on Acetaminophens, Hydroxybenzoic Acids, and Parabens

Influence of Position and Size of Substituents on the Mechanism of Partitioning: A Thermodynamic Study on Acetaminophens, Hydroxybenzoic Acids, and Parabens

Phospholipid-based solid drug formulations for oral bioavailability enhancement: A meta-analysis

On the use of semiempirical models of (solid+supercritical fluid) systems to determine solid sublimation properties

Contact Info

Product

Resources

About