Discovery and development of proton pump inhibitors
Clinical pharmacology
Although the drugs omeprazole, lansoprazole, pantoprazole, and rabeprazole share common structure and mode of action, each differs somewhat in its clinical pharmacology.

Discovery and development of proton pump inhibitors

Section Title: Clinical pharmacology
Table Section Text: Although the drugs omeprazole, lansoprazole, pantoprazole, and rabeprazole share common structure and mode of action, each differs somewhat in its clinical pharmacology.

Compound	Substituents	Form	Cysteine binding	pKa	First approval

X	R1	R2	R3	R4	pKaa1	pKaa1	year

Omeprazole	CH	OCH3	CH3	CH3	CH3	Racemic mixture	813 and 892	4.06	0.79	1989 in USA

Esomeprazole	CH	OCH3	CH3	CH3	CH3	(S)-(−)-enantiomer of omeprazole	813 and 892	4.06	0.79	2001 in USA

Lansoprazole	CH	H	CH3	CH2CF3	H	Racemic mixture	813 and 321	3.83	0.62	1991 in Europe

Dexlansoprazole	CH	H	CH3	CH2CF3	H	(R)-(+)-enantiomer of lansoprazole	813 and 321	3.83	0.62	2009 in USA

Pantoprazole	CH	OCHF2	OCH3	CH3	H	Racemic mixture	813 and 822	3.83	0.11	1994 in Germany

Rabeprazole	CH	H	CH3	(CH2)3OCH3	H	Racemic mixture	813, 892 and 321	4.53	0.62	1999 in USA

Tenatoprazole	N	OCH3	CH3	CH3	CH3	Racemic mixture	813 and 822	4.04	–0.12	—

Sentence(s)

Rabeprazole binds to cysteine 813, 892, and 321.

final_sentence: Rabeprazole binds to cysteine 813, 892, and 321.