Prediction of Partition Coefficients and Permeability of Drug Molecules in Biological Systems with Abraham Model Solute Descriptors Derived from Measured Solubilities and Water-to-Organic Solvent Partition Coefficients

Acree, William E.; Grubbs, Laura M.; Abraham, Michael H.

doi:10.5772/19082

Cited by 7 publications

(3 citation statements)

References 76 publications

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“…However, ET (30) values for other mixtures were not available and excluded from the computations. Furthermore, the Abraham solubility parameters for the investigated solvents were taken from a reference [33]. It is obvious that some of the mentioned cosolvents, like methanol, DMF or 1,4-dioxane, are highly toxic and could not be used in the preparation of oral/parenteral/topical pharmaceutical formulations.…”

Section: Methodsmentioning

confidence: 99%

Prediction of Paracetamol Solubility in Binary Solvents Using Reichardt’s Polarity Parameter Combined Model

Rahimpour,

Jouyban

2023

Liquids

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The objective of this research is to propose a general model utilizing the solvatochromic polarity of electronic transition energy (ET) of the Reichardt indicator to predict paracetamol solubility in the solvent mixtures. In order to model validation, the available ET (30) values of nine aqueous mixtures obtained from existing literature sources were utilized. The trained model yielded a relatively accurate estimation of paracetamol solubility in the investigated systems.

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Section: Methodsmentioning

confidence: 99%

Prediction of Paracetamol Solubility in Binary Solvents Using Reichardt’s Polarity Parameter Combined Model

Rahimpour,

Jouyban

2023

Liquids

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“…The Jouyban model is a generalized one which tries to use the combination of solvent characteristics such as Abraham solvation parameters (AP i ), Hansen solubility parameters (HP i ), and Catalan parameters (CP i ) to correlate the solubility of the solute. The values of those parameters AP i , HP i , and CP i of part of the solvents are listed in Table . ,− Based on the van’t Hoff model and the model parameters AP i , HP i , and CP i , the Jouyban model could be presented as eq . ln ( x 1 ) = ( α 0 + ∑ i = 1 5 α i , A P A P i + ∑ i = 1 3 α i , H P H P i + ∑ i = 1 4 α i , C P C P i ) + ( β 0 + ∑ i = 1 5 β i , A P A ...…”

Section: Solubility Correlationmentioning

confidence: 99%

Solubility Determination and Thermodynamic Correlation for Terbinafine Hydrochloride in Several Mono-solvents from 283.15 to 323.15 K

Yang

Wang

et al. 2023

J. Chem. Eng. Data

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In this paper, the solubility of terbinafine hydrochloride in 13 mono-solvents was measured in the temperature range from 283.15 K to 323.15 K at ambient pressure with the assistance of a laser-based dynamic solubility-monitoring device. It was concluded that the solubility of terbinafine hydrochloride in these mono-solvents increases with rising temperature. At 323.15 K, the molar solubility shows the following order: cyclohexanol (7.739 × 10 −2 ) > n-propyl alcohol (7.351 × 10 −2 ) > n-amyl alcohol (6.967 × 10 −2 ) > iso-butanol (6.932 × 10 −2 ) > n-butanol (6.850 × 10 −2 ) ≈ ethanol (6.778 × 10 −2 ) > isoamyl alcohol (4.926 × 10 −2 ) >1hexanol (4.689 × 10 −2 ) > dimethyl sulfoxide (4.010 × 10 −2 ) > sec-butanol (2.878 × 10 −2 ) > isopropyl alcohol (2.452 × 10 −2 ) > isooctyl alcohol (2.211 × 10 −2 ) > acetonitrile (0.532 × 10 −2 ). Subsequently, the relationship between the solubility of terbinafine hydrochloride and temperature was correlated by six models (Apelblat, van't Hoff, λh, Wilson, NRTL, and Jouyban models), and the mixing thermodynamic properties of the solutions were evaluated with the solubility and the parameters simulated by the Wilson model. In addition, the solvent effect on the solubility of terbinafine hydrochloride was discussed based on the Kamlet−Abboud− Taft linear solvation energy relationships.

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“…The coefficients of the equation are obtained using the multiple linear correlation of the log SP property for a set of compounds to their corresponding descriptor values, and the magnitude and sign of the coefficients provide information on the chemistry of the evaluated system. This equation has been indistinctly applied to numerous solvent partition systems [ 15 , 16 ], to chromatographic partition systems [ 17 , 18 , 19 , 20 ], and also to many environmental [ 21 , 22 , 23 , 24 , 25 ] and biological systems [ 26 , 27 , 28 , 29 , 30 , 31 ]. This implies an important volume of systems that can be compared, in order to identify similarities between them through the coefficients of the equation.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of the Ability of PAMPA Membranes to Emulate Biological Processes through the Abraham Solvation Parameter Model

Soriano-Meseguer

Fuguet

Port³

et al. 2023

Membranes

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Two parallel artificial membrane permeability assay (PAMPA) systems intended for emulating skin permeability have been characterized through the solvation parameter model of Abraham using multilinear regression analysis. The coefficients of the obtained equations have been compared to the ones already established for other PAMPA membranes using statistical tools. The results indicate that both skin membranes are similar to each other in their physicochemical properties. However, they are different from other PAMPA membranes (e.g., intestinal absorption and blood–brain PAMPAs), mainly in terms of hydrophobicity and hydrogen bonding properties. Next, all PAMPA membranes have been compared to relevant biological processes also characterized through the solvation parameter model. The results highlight that skin-PAMPA membranes are a very good choice to emulate skin permeability.

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Prediction of Partition Coefficients and Permeability of Drug Molecules in Biological Systems with Abraham Model Solute Descriptors Derived from Measured Solubilities and Water-to-Organic Solvent Partition Coefficients

Cited by 7 publications

References 76 publications

Prediction of Paracetamol Solubility in Binary Solvents Using Reichardt’s Polarity Parameter Combined Model

Prediction of Paracetamol Solubility in Binary Solvents Using Reichardt’s Polarity Parameter Combined Model

Solubility Determination and Thermodynamic Correlation for Terbinafine Hydrochloride in Several Mono-solvents from 283.15 to 323.15 K

Evaluation of the Ability of PAMPA Membranes to Emulate Biological Processes through the Abraham Solvation Parameter Model

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