In 1997 Christopher A. Lipinski published a seminal paper identifying a series of features commonly found in orally active drugs. These features are referred to as Lipinski's rule of five and can be used as a rule of thumb to indicate whether a molecule is likely to be orally bioavailable (bioactive) (See also ADME). The "rule of five" is so called because most of the features start with the number five. Many drugs are provided in tablet form. ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of medication that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... ADME is an acronym for Absorption, Distribution, Metabolization and Excretion and describes the effectiveness of a pharmaceutical compound within an organism. ...

In general, an orally active drug has:

• not more than 5 hydrogen bond donors (OH and NH groups)
• not more than 10 hydrogen bond acceptors (notably N and O)
• a molecular weight under 500
• a LogP under 5

Lipinski's work has since been extended to include properties such as the number of rings and rotatable bonds. http://www. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless Atomic mass 14. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals Group, Period, Block 16, 2, p Appearance colorless Atomic mass 15. ... The molecular mass of a substance (less accurately called molecular weight and abbreviated as MW) is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... LogP is a measure of differential solubility of a compound in two solvents. ...

References

• CA Lipinski, Adv. Drug Del. Rev. 1997, 23, 3

1997 is a common year starting on Wednesday of the Gregorian calendar. ...

External links

• Interactive Rule of Five calculator