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) Omeprazole, which they called… esomeprazole. Very creative.
So in 2001 when omeprazole lost patent protection, esomeprazole came to market. In theory, you should be able to take a smaller dose of esomeprazole to achieve the same efficacy of omeprazole. Indeed, the top suggested dose of omeprazole is 80 mg, and the top suggested dose of esomeprazole is 40 mg. The only difference between the two drugs is the optical purity. Omeprazole is a racemic mixture, and esomeprazole is optically pure (
So presumably, whatever converts omeprazole or esomeprazole to the active tetracyclic drug does so in a stereoselective fashion "an enzymatic kinetic resolution that's occurring in vivo.
The only reason to take the enantiopure drug is if there are bad side-effects from the racemate "and that could depend on the patient. This however isn't the first example of a chiral switch. There's a good review of the topic here (paywall) http://www.nature.com/nrd/journal/v1/n10/full/nrd915.html
Another reason to take the enantiopure drug is if your copay on the prescription is lower than the cost of the over-the-counter drug.
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