Proton_pump_inhibitors_structure.svg

Summary

Description
English: Common structure of proton pump inhibitors . Asterisk indicates stereocenter . Dots indicate lone pair .
Date
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Author Anypodetos
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Public domain This image of a simple structural formula is ineligible for copyright and therefore in the public domain , because it consists entirely of information that is common property and contains no original authorship.
Compound Substituents Form Cysteine binding pK a First approval
X R 1 R 2 R 3 R 4 pKa a1 pKa a1 year
Omeprazole CH OCH 3 CH 3 CH 3 CH 3 Racemic mixture 813 and 892 4.06 0.79 1989 in USA
Esomeprazole CH OCH 3 CH 3 CH 3 CH 3 ( S )-(−)-enantiomer of lansoprazole 813 and 892 4.06 0.79 2001 in USA
Lansoprazole CH H CH 3 CH 2 CF 3 H Racemic mixture 813 and 321 3.83 0.62 1991 in Europe
Dexlansoprazole CH H CH 3 CH 2 CF 3 H ( R )-(+)-enantiomer of lansoprazole 813 and 321 3.83 0.62 2009 in USA
Pantoprazole CH OCHF 2 OCH 3 CH 3 H Racemic mixture 813 and 822 3.83 0.11 1994 in Germany
Rabeprazole CH H CH 3 (CH 2 ) 3 OCH 3 H Racemic mixture 813, 892 and 321 4.53 0.62 1999 in USA
Tenatoprazole N OCH 3 CH 3 CH 3 CH 3 Racemic mixture 813 and 822 4.04 –0.12 —
W3C-validity not checked.

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inception

7 February 2012