Two decades on from its initial publication, Lipinski’s “rule of five” is arguably one of the most influential concepts in modern drug discovery. Yet it is also one of the most controversial. Developed with the aim of prioritizing the progression of drug candidates with the most promising oral bioavailability properties, Lipinski’s rules have had a lasting effect on drug discovery strategies and the curation of compound screening libraries. They have also inspired the creation of other similar selection criteria, such as GlaxoSmithKline’s 4/400 and Pfizer’s 3/75 rules.
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