metoprolol   

GtoPdb Ligand ID: 553

Synonyms: CGP-2175C | GP-2175E | H-93/26 | Lopressor® | Toprol®
metoprolol is an approved drug (FDA (1978))
Compound class: Synthetic organic
Comment: The approved drug metoprolol is a racemic mixture of two enantiomers. The structure shown here does not specify stereochemistry and represents the mixture. The two enantiomers are represented by PubChem entries CID 157717 and CID 157716.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 50.72
Molecular weight 267.18
XLogP 1.63
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES COCCc1ccc(cc1)OCC(CNC(C)C)O
Isomeric SMILES COCCc1ccc(cc1)OCC(CNC(C)C)O
InChI InChI=1S/C15H25NO3/c1-12(2)16-10-14(17)11-19-15-6-4-13(5-7-15)8-9-18-3/h4-7,12,14,16-17H,8-11H2,1-3H3
InChI Key IUBSYMUCCVWXPE-UHFFFAOYSA-N
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
β1-adrenoceptor Hs Antagonist Antagonist 7.0 – 7.6 pKi - 1-4
pKi 7.0 – 7.6 [1-4]
β2-adrenoceptor Hs Antagonist Antagonist 6.3 pKi - 4
pKi 6.3 [4]
Ligand mentioned in the following text fields