esomeprazole   Click here for help

GtoPdb Ligand ID: 5488

Synonyms: (S)-omeprazole | Nexium®
Approved drug
esomeprazole is an approved drug (FDA (2001), EMA (2013))
Compound class: Synthetic organic
Comment: This drug (the S enantiomer) is a component of the approved drug omeprazole, a racemic mixture of the R and S enantiomers. This drug is a potassium-transporting ATPase inhibitor, commonly referred to as a proton pump inhibitor.
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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES COc1ccc2c(c1)[nH]c(n2)S(=O)Cc1ncc(c(c1C)OC)C
Isomeric SMILES COc1ccc2c(c1)[nH]c(n2)[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)/t24-/m0/s1
InChI Key SUBDBMMJDZJVOS-DEOSSOPVSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2001), EMA (2013))
IUPAC Name Click here for help
6-methoxy-2-[(S)-(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1H-benzimidazole
International Nonproprietary Names Click here for help
INN number INN
7766 esomeprazole
Synonyms Click here for help
(S)-omeprazole | Nexium®
Database Links Click here for help
CAS Registry No. 119141-88-7
ChEBI CHEBI:50275
ChEMBL Ligand CHEMBL1201320
DrugBank Ligand DB00736
DrugCentral Ligand 1055
GtoPdb PubChem SID 178102135
PubChem CID 9568614
Search Google for chemical match using the InChIKey SUBDBMMJDZJVOS-DEOSSOPVSA-N
Search Google for chemicals with the same backbone SUBDBMMJDZJVOS
Search PubMed clinical trials esomeprazole
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UniChem Compound Search for chemical match using the InChIKey SUBDBMMJDZJVOS-DEOSSOPVSA-N
UniChem Connectivity Search for chemical match using the InChIKey SUBDBMMJDZJVOS-DEOSSOPVSA-N
Wikipedia Esomeprazole