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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.

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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)]

Compounds: 15 | Models: 1 | Predictions: 2

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

Regression model (regression)

Open in:QDB Explorer QDB Predictor

Name Type n

R2

σ

Training set training 12 0.948 0.267
Validation set external validation 3 0.990 0.131

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

Compounds: 60 | Models: 1 | Predictions: 2

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

Regression model (regression)

Open in:QDB Explorer QDB Predictor

Name Type n

R2

σ

Training set training 46 0.775 0.410
Validation set i external validation 14 0.167 0.692

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

Compounds: 60 | Models: 1 | Predictions: 2

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

Regression model (regression)

Open in:QDB Explorer QDB Predictor

Name Type n

R2

σ

Training set training 46 0.767 0.417
Validation set i external validation 14 0.448 0.508

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

Compounds: 60 | Models: 1 | Predictions: 2

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

Regression model (regression)

Open in:QDB Explorer QDB Predictor

Name Type n

R2

σ

Training set training 46 0.701 0.398
Validation set i external validation 14 0.403 0.515

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

Compounds: 60 | Models: 1 | Predictions: 2

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

Regression model (regression)

Open in:QDB Explorer QDB Predictor

Name Type n

R2

σ

Training set training 46 0.643 0.429
Validation set i external validation 14 0.327 0.488

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

Compounds: 60 | Models: 1 | Predictions: 2

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

Regression model (regression)

Open in:QDB Explorer QDB Predictor

Name Type n

R2

σ

Training set training 46 0.751 0.436
Validation set i external validation 14 0.651 0.404

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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


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