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
No information available.
Summary of Clinical Use
Used in the management of heart conditions including acute myocardial infarction, angina pectoris, heart failure, and in hypertension. Also used in the treatment of supraventricular and tachyarrhythmias and the prevention of migraine.
Mechanism Of Action and Pharmacodynamic Effects
Antagonist of beta adrenergic receptors. Blockage of these receptors in the heart leads to decreased heart rate, cardiac output and blood pressure.