Predicting aqueous solubility from structure

Delaney, John S.

doi:10.1016/s1359-6446(04)03365-3

Cited by 180 publications

(133 citation statements)

References 51 publications

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“…20,[27][28][29][30] There are examples in the literature which utilize predicted melting points and logP (octanol water partition coefficient) values for solubility predictions via the general solubility equation. 20,30,31 The first principles calculation methods have generally been less accurate and more time consuming, but can provide more fundamental understanding of the process via physically meaningful decomposition of the predicted solution free energy. Recently, much work has focused on improving first principles calculation methods of hydration/solvation free energy and has resulted in much improved methods.…”

Section: Introductionmentioning

confidence: 99%

Are the Sublimation Thermodynamics of Organic Molecules Predictable?

McDonagh

Palmer

Mourik

et al. 2016

J. Chem. Inf. Model.

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We compare a range of computational methods for the prediction of sublimation thermodynamics (enthalpy, entropy and free energy of sublimation). These include a model from theoretical chemistry that utilizes crystal lattice energy minimization (with the DMACRYS program) and QSPR models generated by both machine learning (Random Forest and Support Vector Machines) and regression (Partial Least Squares) methods. Using these methods we investigate the predictability of the enthalpy, entropy and free energy of sublimation, with consideration of whether such a method may be able to improve solubility prediction schemes. Previous work has suggested that the major source of error in solubility prediction schemes involving a thermodynamic cycle via the solid state is in the modeling of the free energy change away from the solid state. Yet contrary to this conclusion other work has found that the inclusion of terms such as the enthalpy of sublimation in QSPR methods 2 does not improve the predictions of solubility. We suggest the use of theoretical chemistry terms, detailed explicitly in the methods section, as descriptors for the prediction of the enthalpy and free energy of sublimation. A dataset of 158 molecules with experimental sublimation thermodynamics values and some CSD refcodes has been collected from the literature and is provided with their original source references.

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Section: Introductionmentioning

confidence: 99%

Are the Sublimation Thermodynamics of Organic Molecules Predictable?

McDonagh

Palmer

Mourik

et al. 2016

J. Chem. Inf. Model.

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“…However, it is more realistic if both the background electrolyte and analyte ions are considered to be only partially ionized. In spite of reliably measured data, acidic and basic dissociation constants of complex molecules like nucleic acids, amino acids/peptides, and glycans holding a charged tag can be estimated by computational methods [45]. COnductor-like Screening MOdel for Real Solvents (COSMO-RS) [46] is one of the most innovative ways to carry out calculations at the molecular level applying ab initio quantum chemistry together with statistical thermodynamics.…”

Section: Electric Field-affected Flowsmentioning

confidence: 99%

Modeling of cell sorting and rare cell capture with microfabricated biodevices

Járvás

Guttman

2013

Trends in Biotechnology

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“…how strongly the molecule associates with the solvent. Compound and solvent entropy also play a role in the regulation of this multi-step operation; having a positive and a negative influence, respectively 3 .…”

Section: Solubilitymentioning

confidence: 99%

Solubility and Dissolution of Drug Product: A Review

Shahrin

2013

Int. J. Pharma Life Sci.

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The oral route of drug administration is the most common and preferred method of delivery due to convenience and ease of ingestion. From a patients perspective, swallowing a dosage form is a comfortable and a familiar means of taking medication. As a result, patient compliance and hence drug treatment is typically more effective with orally administered medications as compared with other routes of administration, for example, parenteral. Although the oral route of administration is preferred, for many drugs it can be a problematic and inefficient mode of delivery for a number of reasons. Limited drug absorption resulting in poor bioavailability is paramount amongst the potential problems that can be encountered when delivering an active agent via the oral route. Drug absorption from the gastrointestinal (GI) tract can be limited by a variety of factors with the most significant contributors being poor aqueous solubility and/or poor membrane permeability of the drug molecule. When delivering an active agent orally, it must first dissolve in gastric and/or intestinal fluids before it can then permeate the membranes of the GI tract to reach systemic circulation. Therefore, a drug with poor aqueous solubility will typically exhibit dissolution rate limited absorption, and a drug with poor membrane permeability will typically exhibit permeation rate limited absorption. Hence, two areas of pharmaceutical research that focus on improving the oral bioavailability of active agents include: (i) enhancing solubility and dissolution rate of poorly water-soluble drugs and (ii) enhancing permeability of poorly permeable drugs. In this article, solubility and dissolution will be discussed.DOI: http://dx.doi.org/10.3329/ijpls.v2i1.15133 International Journal of Pharmaceutical and Life Sciences Vol.2(1) 2013: 33-41

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Predicting aqueous solubility from structure

Cited by 180 publications

References 51 publications

Are the Sublimation Thermodynamics of Organic Molecules Predictable?

Are the Sublimation Thermodynamics of Organic Molecules Predictable?

Modeling of cell sorting and rare cell capture with microfabricated biodevices

Solubility and Dissolution of Drug Product: A Review

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