Thermodynamics of solutions: II. Flurbiprofen and diflunisal as models for studying solvation of drug substances
Three independent methods (sublimation, solubility and solution calorimetry) were used to study the dissolution and solvation processes of diflunisal (DIF) and flurbiprofen (FBP). Thermodynamic functions for the sublimation of DIF and FBP were obtained. Concentrations of saturated solutions and stan...
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Published in | European journal of pharmaceutical sciences Vol. 19; no. 5; pp. 423 - 432 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
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Elsevier B.V
01.08.2003
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Abstract | Three independent methods (sublimation, solubility and solution calorimetry) were used to study the dissolution and solvation processes of diflunisal (DIF) and flurbiprofen (FBP). Thermodynamic functions for the sublimation of DIF and FBP were obtained. Concentrations of saturated solutions and standard solution enthalpies of DIF and FBP in aliphatic alcohols and individual organic solvents were measured. Correlation analysis between: (a) the thermodynamic functions for a substance in various solvents, and (b) the same functions for different compounds was carried out. The investigated substances can be arranged with increasing Gibbs energy of solvation as follows: benzoic acid<DIF<FBP. Enthalpy is found to be the major driving force of the solvation process for all the studied compounds. The ratio of specific and nonspecific solute–solvent interaction in terms of enthalpies (
ε
H) and in terms of entropies (
ε
S) was analyzed. Based on the experimental data, a compensation effect of thermodynamic solubility functions of the investigated substances both in alcohols and in organic solvents was found. |
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AbstractList | Three independent methods (sublimation, solubility and solution calorimetry) were used to study the dissolution and solvation processes of diflunisal (DIF) and flurbiprofen (FBP). Thermodynamic functions for the sublimation of DIF and FBP were obtained. Concentrations of saturated solutions and standard solution enthalpies of DIF and FBP in aliphatic alcohols and individual organic solvents were measured. Correlation analysis between: (a) the thermodynamic functions for a substance in various solvents, and (b) the same functions for different compounds was carried out. The investigated substances can be arranged with increasing Gibbs energy of solvation as follows: benzoic acid<DIF<FBP. Enthalpy is found to be the major driving force of the solvation process for all the studied compounds. The ratio of specific and nonspecific solute–solvent interaction in terms of enthalpies (
ε
H) and in terms of entropies (
ε
S) was analyzed. Based on the experimental data, a compensation effect of thermodynamic solubility functions of the investigated substances both in alcohols and in organic solvents was found. Three independent methods (sublimation, solubility and solution calorimetry) were used to study the dissolution and solvation processes of diflunisal (DIF) and flurbiprofen (FBP). Thermodynamic functions for the sublimation of DIF and FBP were obtained. Concentrations of saturated solutions and standard solution enthalpies of DIF and FBP in aliphatic alcohols and individual organic solvents were measured. Correlation analysis between: (a) the thermodynamic functions for a substance in various solvents, and (b) the same functions for different compounds was carried out. The investigated substances can be arranged with increasing Gibbs energy of solvation as follows: benzoic acid<DIF<FBP. Enthalpy is found to be the major driving force of the solvation process for all the studied compounds. The ratio of specific and nonspecific solute-solvent interaction in terms of enthalpies (epsilon (H)) and in terms of entropies (epsilon (S)) was analyzed. Based on the experimental data, a compensation effect of thermodynamic solubility functions of the investigated substances both in alcohols and in organic solvents was found. |
Author | Perlovich, German L. Kurkov, Sergey V. Bauer-Brandl, Annette |
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BackLink | https://www.ncbi.nlm.nih.gov/pubmed/12907293$$D View this record in MEDLINE/PubMed |
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Keywords | Solvation Compensation effect Organic solvents Sublimation Solubility Diflunisal Flurbiprofen |
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References_xml | – volume: 79 start-page: 1109 year: 1990 end-page: 1115 ident: BIB9 article-title: Effects of solvent medium on solubility. V: Enthalpic and entropic contributions to the free energy changes of di-substituted benzene derivatives in ethanol:water and ethanol:cyclohexane mixtures publication-title: J. Pharm. Sci. contributor: fullname: Ahumada – volume: 28 start-page: 737 year: 1999 end-page: 751 ident: BIB15 article-title: Aqueous solubilities, infinite dilution activity coefficients and octanol–water partition coefficients of tricyclic analogues of acyclovir publication-title: J. Solut. Chem. contributor: fullname: Kozbial – volume: 73 start-page: 1572 year: 1969 end-page: 1580 ident: BIB8 article-title: Solvation enthalpies of various nonelectrolytes in water, propylene carbonate and dimethyl sulfoxide publication-title: J. Phys. Chem. contributor: fullname: Friedmann – volume: 54 start-page: 1622 year: 1984 end-page: 1632 ident: BIB13 article-title: Solvation of organic compounds. Molecular refraction, dipole moment and heat of solvation publication-title: Russ. Zh. Obshch. Khim. contributor: fullname: Antipin – volume: 10 start-page: 414 year: 1973 end-page: 482 ident: BIB6 article-title: On enthalpy–entropy relationship publication-title: Prog. Phys. Org. Chem. contributor: fullname: Exner – volume: 87 start-page: 1590 year: 1998 end-page: 1596 ident: BIB2 article-title: Enthalpy–entropy compensation for the solubility of drugs in solvent mixtures: paracetamol, acetanilide, and nalidixic acid in dioxane:water publication-title: J. Pharm. Sci. contributor: fullname: Reillo – volume: 95 start-page: 5897 year: 1973 end-page: 5900 ident: BIB7 article-title: Aromatic substituent group enthalpies of transfer from methanol to publication-title: J. Am. Chem. Soc. contributor: fullname: Rodewald – volume: Vol. 14 start-page: 491 year: 1985 end-page: 526 ident: BIB3 article-title: Diflunisal publication-title: Analytical Profiles of Drug Substances contributor: fullname: Hux – volume: 13 start-page: 115 year: 1983 end-page: 144 ident: BIB14 article-title: Enthalpy–entropy compensation analysis of pharmaceutical, biochemical and biological systems publication-title: Int. J. Pharm. contributor: fullname: Tomlinson – volume: 57 start-page: 225 year: 1999 end-page: 234 ident: BIB16 article-title: The vapour pressure and the enthalpy of sublimation determination by inert gas flow method publication-title: J. Thermal Anal. Calorimetry contributor: fullname: Wszelaka-Rylik – volume: 91 start-page: 1036 year: 2002 end-page: 1045 ident: BIB11 article-title: Interrelation between thermochemical and structural data of polymorphs exemplified by Diflunisal publication-title: J. Pharm. Sci. contributor: fullname: Bauer-Brandl – volume: 92 start-page: 2365 year: 1970 end-page: 2377 ident: BIB1 article-title: Studies of hydrogen-bonded complex formation III. Thermodynamics of complexing by infrared spectroscopy and calorimetry publication-title: J. Am. Chem. Soc. contributor: fullname: Schleyer – year: 1970 ident: BIB4 publication-title: Thermochemistry of Organic and Organometallic Compounds contributor: fullname: Pilcher – volume: 29 start-page: 1094 year: 1964 end-page: 1113 ident: BIB5 article-title: On the enthalpy–entropy relationship publication-title: Coll. Czech. Commun. contributor: fullname: Exner |
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Snippet | Three independent methods (sublimation, solubility and solution calorimetry) were used to study the dissolution and solvation processes of diflunisal (DIF) and... |
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SubjectTerms | Alcohols - chemistry Algorithms Calorimetry, Differential Scanning Compensation effect Diflunisal Diflunisal - chemistry Entropy Flurbiprofen Flurbiprofen - chemistry Organic solvents Pharmaceutical Solutions - chemistry Regression Analysis Solubility Solvation Solvents Sublimation Thermodynamics |
Title | Thermodynamics of solutions: II. Flurbiprofen and diflunisal as models for studying solvation of drug substances |
URI | https://dx.doi.org/10.1016/S0928-0987(03)00145-3 https://www.ncbi.nlm.nih.gov/pubmed/12907293 https://search.proquest.com/docview/73546981 |
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