Correlation of aqueous solubility of salts of benzylamine with experimentally and theoretically derived parameters. A multivariate data analysis approach

Parshad, Henrik; Frydenvang, Karla; Liljefors, Tommy; Larsen, Claus

doi:10.1016/s0378-5173(02)00042-x

Cited by 37 publications

(25 citation statements)

References 32 publications

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“…This last observation is surprising because many previous studies have shown correlation between these two features for both salt and cocrystal forms. [15,34,35] Measurement of solubility is notoriously variable and observed results are highly dependent upon method used. [36] The free acid solubility values used here were averages taken from a literature compendium rather than measured using a similar method to that used for the salt forms.…”

Section: Correlation Of Physical Properties For (1r2s)(-) Methylephementioning

confidence: 99%

Aqueous Solubility of Organic Salts. Investigating Trends in a Systematic Series of 51 Crystalline Salt Forms of Methylephedrine

Moraes

Edwards

Florence

et al. 2017

Crystal Growth & Design

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This version is available at https://strathprints.strath.ac.uk/60530/ Strathprints is designed to allow users to access the research output of the University of Strathclyde. Unless otherwise explicitly stated on the manuscript, Copyright © and Moral Rights for the papers on this site are retained by the individual authors and/or other copyright owners. Please check the manuscript for details of any other licences that may have been applied. You may not engage in further distribution of the material for any profitmaking activities or any commercial gain. You may freely distribute both the url (https://strathprints.strath.ac.uk/) and the content of this paper for research or private study, educational, or not-for-profit purposes without prior permission or charge.Any correspondence concerning this service should be sent to the Strathprints administrator: strathprints@strath.ac.ukThe Strathprints institutional repository (https://strathprints.strath.ac.uk) is a digital archive of University of Strathclyde research outputs. It has been developed to disseminate open access research outputs, expose data about those outputs, and enable the management and persistent access to Strathclyde's intellectual output. AbstractA dataset consisting of structures and aqueous solubility and melting point data for 51 salt forms of the phenylethylamine base methylephedrine is presented. Analysis showed correlation between solubility and melting point and between melting point of the salt and melting point of the parent acid, but no correlation of salt solubility with solubility of the parent acid.Identification of associations was aided by examining chemically sensible subgroups of the dataset, and this approach highlighted significantly different relationships between solubility and melting point for these subgroups. Thus, for example, the expected negative correlation between solubility and melting point was found for 24 anhydrous benzoate salts, but a positive correlation observed for 8 halide salts. Hydrated forms were anomalous. Packing analysis identified groups of structures that were isostructural with respect to cation packing. Correlation between solubility and melting point was found to be greatest within these isostructural groups, implying a role for packing structure in determining solubility.

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Section: Correlation Of Physical Properties For (1r2s)(-) Methylephementioning

confidence: 99%

Aqueous Solubility of Organic Salts. Investigating Trends in a Systematic Series of 51 Crystalline Salt Forms of Methylephedrine

Moraes

Edwards

Florence

et al. 2017

Crystal Growth & Design

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show abstract

“…[40][41][42][43] Parshad et al developed a model for the solubility of benzylamine salts with a combination of experimental and theoretical descriptors. 42 The best purely computational model employed the Charton steric parameter, Hansch parameters, and the MW of the salt, resulting in R 2 = 0.73 for the training data and R 2 = 0.70 for the validation data. Tantishaiyakul 41 reused the benzylamine data set to develop a computational neural network model using only calculated descriptors.…”

Section: E29mentioning

confidence: 99%

Recent progress in the computational prediction of aqueous solubility and absorption

Johnson

Zheng

2006

AAPS J

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The computational prediction of aqueous solubility and/or human absorption has been the goal of many researchers in recent years. Such an in silico counterpart to the biopharmaceutical classifi cation system (BCS) would have great utility. This review focuses on recent developments in the computational prediction of aqueous solubility, P-glycoprotein transport, and passive absorption. We fi nd that, while great progress has been achieved, models that can reliably affect chemistry and development are still lacking. We briefl y discuss aspects of emerging scientifi c understanding that may lead to breakthroughs in the computational modeling of these properties.

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“…There was a study concerning QSPR of salt solubility indicating that no correlation was found between diclofenac salt solubility and any one parameter of either pK a , hydrophilicity, or melting point of counter-ions [1]. Parshad et al have recently reported models for predicting aqueous solubility of benzylamine salts, and their best models using different set of descriptors gave R 2 of 0.82 and Q 2 of 0.72 for training set, and R 2 of 0.74 and Q 2 of 0.72 for test set [10]. Intrinsic dissolution rate, intrinsic solubility of unionized acids, Charton's steric parameter, Hansch hydrophobic parameter, and molecular weight (MW) were reported as important descriptors for their derived models.…”

Section: Introductionmentioning

confidence: 97%

“…The objective of this investigation is to model experimentally determined solubility of salts from computationally derived molecular descriptors, and to compare the predictive performance of PLS and ANN methods. The same set of salts from Parshad et al was employed in this study [10].…”

Section: Introductionmentioning

confidence: 99%

Prediction of the aqueous solubility of benzylamine salts using QSPR model

Tantishaiyakul

2005

Journal of Pharmaceutical and Biomedical Analysis

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Correlation of aqueous solubility of salts of benzylamine with experimentally and theoretically derived parameters. A multivariate data analysis approach

Cited by 37 publications

References 32 publications

Aqueous Solubility of Organic Salts. Investigating Trends in a Systematic Series of 51 Crystalline Salt Forms of Methylephedrine

Aqueous Solubility of Organic Salts. Investigating Trends in a Systematic Series of 51 Crystalline Salt Forms of Methylephedrine

Recent progress in the computational prediction of aqueous solubility and absorption

Prediction of the aqueous solubility of benzylamine salts using QSPR model

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