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
References
1. Baker JG. (2005)
The selectivity of beta-adrenoceptor antagonists at the human beta1, beta2 and beta3 adrenoceptors.
Br. J. Pharmacol., 144 (3): 317-22. [PMID:15655528]
2. Candelore MR, Deng L, Tota L, Guan XM, Amend A, Liu Y, Newbold R, Cascieri MA, Weber AE. (1999)
Potent and selective human beta(3)-adrenergic receptor antagonists.
J. Pharmacol. Exp. Ther., 290 (2): 649-55. [PMID:10411574]
3. Hoffmann C, Leitz MR, Oberdorf-Maass S, Lohse MJ, Klotz KN. (2004)
Comparative pharmacology of human beta-adrenergic receptor subtypes--characterization of stably transfected receptors in CHO cells.
Naunyn Schmiedebergs Arch. Pharmacol., 369 (2): 151-9. [PMID:14730417]
4. Louis SN, Nero TL, Iakovidis D, Jackman GP, Louis WJ. (1999)
LK 204-545, a highly selective beta1-adrenoceptor antagonist at human beta-adrenoceptors.
Eur. J. Pharmacol., 367 (2-3): 431-5. [PMID:10079020]