Lipinski's Rule of Five



 It has been suggested that this article or section be merged into Druglikeness. (Discuss)

Lipinski's Rule of Five is a rule of thumb to evaluate molecules.[1]

The rule describes molecular properties important for a drug's ADME"). However, the rule does not predict if a compound is pharmacologically active.

The rule is important for bonds, and a higher lipophilicity.[2]

The rule

Lipinski's Rule of Five states that, in general, an orally active drug has:

Note that all numbers are multiples of five, which is the origin of the rule's name.

Improvements

To evaluate druglikeness better, the rules have spawned many extensions, for example one from a 1999 paper by Ghose et al.:[3]

  • Partition coefficient log P in -0.4 to +5.6 range
  • Molar refractivity from 40 to 130
  • Molecular weight from 160 to 480
  • Number of heavy atoms from 20 to 70

Over the past decade Lipinski's profiling tool for druglikeness has led to further investigations by scientists to extend profiling tools to lead-like properties of compounds in the hope that a better starting point in early discovery can save time and cost.

See also

References

  1. ^ C. A. Lipinski, F. Lombardo, B. W. Dominy, P. J. Feeney, Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings, Adv. Drug Del. Rev., 2001, 46, 3-26. (doi:10.1016/S0169-409X(00)00129-0)
  2. ^ T. I. Oprea, A. M. Davis, S. J. Teague, P. D. Leeson, Is There a Difference between Leads and Drugs? A Historical Perspective, J. Chem. Inf. Comput. Sci., 2001, 41, 1308-1315.
  3. ^ Arup K. Ghose, Vellarkad N. Viswanadhan, and John J. Wendoloski, A Knowledge-Based Approach in Designing Combinatorial or Medicinal Chemistry Libraries for Drug Discovery, J. Combin. Chem., 1999, 1, 55-68. (doi:10.1021/cc9800071)
 
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