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| Keywords: Proton pump inhibitors structure.svg proton pump inhibitor s Asterisk indicates stereocenter Dots indicate lone pair own Anypodetos 2012-02-07 pd-chem wikitable style margin 1em auto 1em auto; - rowspan 2 Compound colspan 5 Substituents rowspan 2 Form rowspan 2 Cysteine binding colspan 2 pK<sub>a</sub> First approval - X R<sup>1</sup> R<sup>2</sup> R<sup>3</sup> R<sup>4</sup> pKa<sub>a1</sub> pKa<sub>a1</sub> year - Omeprazole CH OCH<sub>3</sub> CH<sub>3</sub> CH<sub>3</sub> CH<sub>3</sub> Racemic mixture 813 and 892 4 06 0 79 1989 in USA - Esomeprazole CH OCH<sub>3</sub> CH<sub>3</sub> CH<sub>3</sub> CH<sub>3</sub> S - ˆ’ -enantiomer of lansoprazole 813 and 892 4 06 0 79 2001 in USA - Lansoprazole CH H CH<sub>3</sub> CH<sub>2</sub>CF<sub>3</sub> H Racemic mixture 813 and 321 3 83 0 62 1991 in Europe - Dexlansoprazole CH H CH<sub>3</sub> CH<sub>2</sub>CF<sub>3</sub> H R - + -enantiomer of lansoprazole 813 and 321 3 83 0 62 2009 in USA - Pantoprazole CH OCHF<sub>2</sub> OCH<sub>3</sub> CH<sub>3</sub> H Racemic mixture 813 and 822 3 83 0 11 1994 in Germany - Rabeprazole CH H CH<sub>3</sub> CH<sub>2</sub> <sub>3</sub>OCH<sub>3</sub> H Racemic mixture 813 892 and 321 4 53 0 62 1999 in USA - Tenatoprazole N OCH<sub>3</sub> CH<sub>3</sub> CH<sub>3</sub> CH<sub>3</sub> Racemic mixture 813 and 822 4 04 “0 12 ” valid svg Cc-zero Proton pump inhibitors | ||||
