Oja, M.; Maran, U. Quantitative structure-permeability relationships at various pH values for neutral and amphoteric drugs and drug-like compounds. SAR QSAR Environ. Res. 2016, 27, 813-832.

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Oja, M.; Maran, U. Quantitative structure-permeability relationships at various pH values for neutral and amphoteric drugs and drug-like compounds. SAR QSAR Environ. Res. 2016, 27, 813-832.

QDB archive DOI: 10.15152/QDB.184   DOWNLOAD

QsarDB content

Property LogPeff_average: Average logarithmic effective membrane permeability for pH range 3 to 9 of neutral compounds [log(cm/s)]

Eq.9: QSAR model for average membrane permeability of neutral compounds

Regression model (regression)

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NameTypen

R2

σ

Training settraining120.9480.267
Validation setexternal validation30.9900.131

Property LogPeff_pH3: Logarithmic effective membrane permeability of amphoteric compounds at pH 3 [log(cm/s)]

Eq.11: QSAR model for membrane permeability of amphoteric compounds at pH 3

Regression model (regression)

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NameTypen

R2

σ

Training settraining460.7750.410
Validation set iexternal validation140.1670.692

Property LogPeff_pH5: Logarithmic effective membrane permeability of amphoteric compounds at pH 5 [log(cm/s)]

Eq.12: QSAR model for membrane permeability of amphoteric compounds at pH 5

Regression model (regression)

Open in:QDB ExplorerQDB Predictor

NameTypen

R2

σ

Training settraining460.7670.417
Validation set iexternal validation140.4480.508

Property LogPeff_pH7.4: Logarithmic effective membrane permeability of amphoteric compounds at pH 7.4 [log(cm/s)]

Eq.13: QSAR model for membrane permeability of amphoteric compounds at pH 7.4

Regression model (regression)

Open in:QDB ExplorerQDB Predictor

NameTypen

R2

σ

Training settraining460.7010.398
Validation set iexternal validation140.4030.515

Property LogPeff_pH9: Logarithmic effective membrane permeability of amphoteric compounds at pH 9 [log(cm/s)]

Eq.14: QSAR model for membrane permeability of amphoteric compounds at pH 9

Regression model (regression)

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NameTypen

R2

σ

Training settraining460.6430.429
Validation set iexternal validation140.3270.488

Property LogPeff_highest: Highest logarithmic effective membrane permeability for pH range 3 to 9 of amphoteric compounds [log(cm/s)]

Eq.15: QSAR model for highest membrane permeability of amphoteric compounds

Regression model (regression)

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NameTypen

R2

σ

Training settraining460.7510.436
Validation set iexternal validation140.6510.404

Citing

When using this QDB archive, please cite (see details) it together with the original article:

  • Oja, M.; Maran, U. Data for: Quantitative structure-permeability relationships at various pH values for neutral and amphoteric drugs and drug-like compounds. QsarDB repository, QDB.184. 2016. http://dx.doi.org/10.15152/QDB.184

  • Oja, M.; Maran, U. Quantitative structure-permeability relationships at various pH values for neutral and amphoteric drugs and drug-like compounds. SAR QSAR Environ. Res. 2016, 27, 813-832. http://dx.doi.org/10.1080/1062936X.2016.1238408

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Title: Oja, M.; Maran, U. Quantitative structure-permeability relationships at various pH values for neutral and amphoteric drugs and drug-like compounds. SAR QSAR Environ. Res. 2016, 27, 813-832.
Abstract:Human intestinal absorption is a key property for orally administered drugs and is dependent on pH. This study focuses on neutral and amphoteric compounds and their membrane permeabilities across the range of pH values found in the human intestine. The membrane permeability values for 15 neutral and 60 amphoteric compounds at pH 3, 5, 7.4 and 9 were measured using the parallel artificial membrane permeability assay (PAMPA). For each data series the quantitative structure-permeability relationships were developed and analysed. The results show that the membrane permeability of neutral compounds is attributed to a single structural characteristic, the hydrogen bond donor ability. Amphoteric compounds are more complex because of their chemical constitution, and therefore require three-parameter models to describe and predict membrane permeability. Analysis of the models for amphoteric compounds reveals that membrane permeability depends on multiple structural characteristics; the partition coefficient, hydrogen bond properties and the shape of the molecules. In addition to conventional validation strategies, two external compounds (isradipine and omeprazole) were tested and revealed very good agreement of pH profiles between experimental and predicted membrane permeability for all of the developed models.
URI:http://hdl.handle.net/10967/184
http://dx.doi.org/10.15152/QDB.184
Date:2016-09-14
Funding:This work was supported by the Estonian Ministry for Education and Research [grant number IUT34-14].


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