Polar surface area

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The polar surface area (PSA) of a molecule is defined as the surface sum over all polar atoms, primarily oxygen and nitrogen, also including their attached hydrogens.

PSA is a commonly used medicinal chemistry metric for the optimisation of a drug's ability to permeate cells. Molecules with a polar surface area of greater than 140 angstroms squared tend to be poor at permeating cell membranes. For molecules to penetrate the blood-brain barrier (and thus act on receptors in the central nervous system), a PSA less than 90 angstroms squared is usually needed.

Video Polar surface area

See also

• Biopharmaceutics Classification System
• Cheminformatics
  • Chemistry Development Kit
  • JOELib
• Implicit solvation
• Lipinski's rule of five

Maps Polar surface area

References

• Pajouhesh H, Lenz GR. Medicinal Chemical Properties of Successful Central Nervous System Drugs. NeuroRx. 2005 Oct; 2(4): 541-553. doi:10.1602/neurorx.2.4.541
• Clark, D.E., Rapid calculation of polar molecular surface area and its application to the prediction of transport phenomena. 1. Prediction of intestinal absorption. J.Pharm.Sci. 1999, 88, 807-814. (doi:10.1021/js9804011)
• Palm, K., Stenberg, P., Luthman, K., Artursson, P. Polar molecular surface properties predict the intestinal absorption of drugs in humans. Pharm. Res. 1997, 14, 568-571. (doi:10.1023/A:1012188625088)
• Ertl, P., Rohde, B., Selzer, P. Fast calculation of molecular polar surface area as a sum of fragment based contributions and its application to the prediction of drug transport properties. J. Med. Chem. 2000, 43, 3714-3717. (doi:10.1021/jm000942e)
• Ertl, P. Polar Surface Area, in Molecular Drug Properties, R. Mannhold (ed), Wiley-VCH, pp. 111-126, 2007
• Shityakov, S., Neuhaus, W., Dandekar, T., Förster, C. Analysing molecular polar surface descriptors to predict blood-brain barrier permeation. Int. J. Comput. Biol. Drug Des. 2013, 6(1-2), 146-156. (doi: 10.1504/IJCBDD.2013.052195)

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External links

• Interactive Polar Surface Area calculator
• Free, Programmable TPSA Calculator

Source of article : Wikipedia