omeprazole   Click here for help

GtoPdb Ligand ID: 4279

Synonyms: H 168/68 | Losec® | Prilosec®
Approved drug
omeprazole is an approved drug (FDA (1989))
Compound class: Synthetic organic
Comment: This approved drug omeprazole is a racemic mixture of the R and S stereoisomers. Omeprazole is a potassium-transporting ATPase inhibitor, commonly referred to as a proton pump inhibitor.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 96.31
Molecular weight 345.11
XLogP 0.6
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES COc1ccc2c(c1)nc([nH]2)S(=O)Cc1ncc(c(c1C)OC)C
Isomeric SMILES COc1ccc2c(c1)nc([nH]2)S(=O)Cc1ncc(c(c1C)OC)C
InChI InChI=1S/C17H19N3O3S/c1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)
InChI Key SUBDBMMJDZJVOS-UHFFFAOYSA-N
References
1. Adelstein GW, Yen CH, Haack RA, Yu S, Gullikson G, Price DV, Anglin C, Decktor DL, Tsai H, Keith RH. (1988)
Substituted 2-[(2-benzimidazolylsulfinyl)methyl]anilines as potential inhibitors of H+/K+ ATPase.
J. Med. Chem., 31 (6): 1215-20. [PMID:2836591]
2. Sanfilippo PJ, Urbanski M, Press JB, Hajos ZG, Shriver DA, Scott CK. (1988)
Synthesis of (aryloxy)alkylamines. 1. Novel antisecretory agents with H+K+-ATPase inhibitory activity.
J. Med. Chem., 31 (9): 1778-85. [PMID:2842503]