Human Skin Permeation and Partition: General Linear Free‐Energy Relationship Analyses

Descriptors have been determined for four inorganic mercury(II) species and for seventeen organic mercury(II) species, using experimental literature data. These descriptors can then be used in equations that we have already set out in order to estimate a large number of physicochemical properties. These include the water to octanol partition coefficient and the gas to water partition coefficient. For the organic mercury(II) species, including dimethylmercury and the methylmercury(II) halides, the latter has been estimated over the temperature range 273-373 K.Eqn ( 2) is used for gas to solvent partitions, as log K s , where K s is defined similarly to K w . Both eqn (1) and eqn (2) can be used for the gas to water partition. The independent variables in eqn (1) and eqn (2) are solute descriptors as follows. 10,11 E is the solute excess molar refraction in units of (cm 3 mol À1 )/10, S is the solute dipolarity/polarizability, A and B are the overall or summation hydrogen bond acidity and basicity, V is the McGowan characteristic volume 27 in units of (cm 3 mol À1 )/100, and L is the logarithm of the gas to hexadecane partition coefficient at 298 K.The use of eqn (1) and eqn (2) in the determination of descriptors has been described in detail, 10,11 and numerous examples are available. [28][29][30][31][32] Equations on the lines of eqn (1) and eqn (2) are set

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“…The relevant equations are eqn. (14) and eqn. (15) from which we can predict partition coefficients for mercury.…”

Section: Discussionmentioning

confidence: 99%

Solvation parameters for mercury and mercury(ii) compounds: calculation of properties of environmental interest

et al. 2008

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“…Abraham and Martins (2004) calculated the fivedimensional distance between the coefficients as points in five-dimensional space by straightforward geometry 22 2 2 2 i D i s t a n c e ( e )(…”

Section: Abraham Solvation Parameter Modelmentioning

confidence: 99%

“…Highly lipophilic compounds (those with log P OtOH/water > 5) pass easily through the stratum corneum, but are generally too water-insoluble to pass through the remaining epidermis sub-layers to enter the blood stream. There has been increasing experimental evidence that ionized species can contribute to transdermal absorption (Netzlaff et al, 2006;Abraham and Martins, 2004;Michaels et al, 1975). When the penetrating compound can exist in both ionized and unionized forms, it is the unionized form that penetrates faster through the lipid regions.…”

Section: Abraham Solvation Parameter Model: Prediction Of Water-to-skmentioning

confidence: 99%

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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

Acree¹,

Grubbs²,

Abraham³

2012

Toxicity and Drug Testing

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“…distribution from blood to the various body organs [15][16][17][18][19][20], permeability of organic compounds through human skin from aqueous solution [21], brain permeation of neutral molecules and ionic species [22], and enthalpies of solvation of organic vapors and gases in both water [23] and in organic solvent media [23][24][25][26][27][28][29][30][31][32]. The molecular descriptors may be of either experimental origin or calculated based solely on molecular structure considerations.…”

Section: Introductionmentioning

confidence: 99%

Enthalpy of solvation correlations for organic solutes and gases dissolved in 1-propanol and tetrahydrofuran

et al. 2011

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Data have been assembled from the published literature on the enthalpies of solvation for 103 organic vapors and gaseous solutes in 1-propanol and for 86 gaseous compounds in tetrahydrofuran. It is shown that an Abraham solvation equation with five descriptors can be used to correlate the experimental solvation enthalpies to within standard deviations of 2.35 kJ/mole and 2.10 kJ/mole for 1-propanol and tetrahydrofuran, respectively. The derived correlations provide very accurate mathematical descriptions of the measured enthalpy of solvation data at 298 K, which in the case of 1-propanol span a range of 119 kJ/mole. Division of the experimental values into a training set and a test set shows that there is no bias in predictions, and that the predictive capability of the correlations is better than 3.5 kJ/mole.

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Human Skin Permeation and Partition: General Linear Free‐Energy Relationship Analyses

Cited by 190 publications

References 73 publications

Solvation parameters for mercury and mercury(ii) compounds: calculation of properties of environmental interest

Solvation parameters for mercury and mercury(ii) compounds: calculation of properties of environmental interest

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

Enthalpy of solvation correlations for organic solutes and gases dissolved in 1-propanol and tetrahydrofuran

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