Drug chirality is now a major theme in the design, discovery and development of new drugs [1].An analysis of the worldwide approved drugs according to chirality character (single enantiomers, racemates and achirals) in 1983-2004 and of the New Molecular Entities that were approved by the US FDA in 1991-2004 indicates that the approval of single enantiomers has been significant since the 1980s [2].There is a gradual increase in the percentile of single-enantiomer drugs reaching the market.Of the 46 top pharmaceuticals that had a major impact on human health and society [3], the majority are single enantiomers, followed by achirals and the minority are racemates.However, racemic drugs should not be declared a dead option.A principal scenario in chiral drug development is a switch from an existing racemic drug to one of its enantiomers.Chiral Switches [4-5] are chiral drugs that have been claimed, approved and marketed as racemates or as mixtures of diastereomers, but have since been redeveloped as single enantiomers.The essential criterion of a chiral switch is a change in the status of chirality.Often, racemic drugs undergoing expirations of patents and market exclusivities are subjected to chiral switches.The primrose paths of chiral switches at the level of intellectual property in 2002-2005 will be highlighted.Patents claiming single-enantiomer drugs are frequently challenged.Cases in point are the antiplatelet (S)-(+)-Clopidogrel Bisulfate (Plavix(R)) and the antibacterial (S)-(-)-Levofloxacin (Levaquin(R)).Recent developments in the strategy of chiral switches of drugs will be discussed.