{2-hydroxy-3-[4-(2-methoxyethyl)phenoxy]propyl}(propan-2-yl)amine

• ChemBase ID: 149
• Molecular Formular: C15H25NO3
• Molecular Mass: 267.3639
• Monoisotopic Mass: 267.18344367
• SMILES: O(CC(O)CNC(C)C)c1ccc(CCOC)cc1
• Canonical 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
• InChIKey: IUBSYMUCCVWXPE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {2-hydroxy-3-[4-(2-methoxyethyl)phenoxy]propyl}(propan-2-yl)amine
• IUPAC Traditional name: metoprolol
• Brand Name: Beloc; Betaloc; Lopressor HCT; Lopresor; Lopresoretic; Lopressor; Metroprolol; Prelis; Selo-Zok; Seloken; Selopral; Toprol; Toprol-XL; Toprol XL; Lopressor, Toprol-xl
• Synonyms: Metoprolol Tartrate; Metoprolol succinate; Metoprolol

Database IDs

• CAS Number: 51384-51-1; 37350-58-6
• PubChem SID: 46506211; 160963612
• PubChem CID: 4171
• CHEBI ID: 6904
• ATC CODE: C07AB02
• CHEMBL: 13
• Chemspider ID: 4027
• DrugBank ID: DB00264
• IUPHAR ligand ID: 553
• KEGG ID: D02358
• Unique Ingredient Identifier: GEB06NHM23
• Wikipedia Title: Metoprolol
• Medline Plus: a682864

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.087972
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.4345746
• LogD (pH = 7.4): -0.46658155
• Log P: 1.7586571
• Molar Refractivity: 76.6976 cm^3
• Polarizability: 30.335455 Å^3
• Polar Surface Area: 50.72 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.8
• LOG S: -2.82
• Solubility (Water): 4.02e-01 g/l

PROPERTIES

Physical Property

• Solubility: 16.9 mg/mL
• Melting Point: 120°C (248°F)
• Hydrophobicity(logP): 1.6

Pharmacology Properties

• Admin Routes: Oral, IV
• Bioavailability: 12%
• Excretion: Renal
• Half Life: 3-7 hours
• Metabolism: Hepatic via CYP2D6, CYP3A4
• Legal Status: Rx-only
• Pregnancy Category: C (Australia); C (US)
• US Licence: Metoprolol

DETAILS

DrugBank - DB00264

• Drug Groups: approved; investigational
• Description: Metoprolol is a cardioselective β1-adrenergic blocking agent used for acute myocardial infarction (MI), heart failure, angina pectoris and mild to moderate hypertension. It may also be used for supraventricular and tachyarrhythmias and prophylaxis for migraine headaches. Metoprolol is structurally similar to bisoprolol, acebutolol and atenolol in that it has two substituents in the para position of the benzene ring. The β1-selectivity of these agents is thought to be due in part to the large substituents in the para position. At low doses, metoprolol selectively blocks cardiac β-1-adrenergic receptors with little activity against β2-adrenergic receptors of the lungs and vascular smooth muscle. Receptor selectivity decreases with higher doses. Unlike propranolol and pindolol, metoprolol does not exhibit membrane-stabilizing or intrinsic sympathomimetic activity. Membrane-stabilizing effects are only observed at doses much higher than those needed for β-adrenergic blocking activity. Metoprolol possesses a single chiral centre and is administered as a racemic mixture.
• Indication: For the management of acute myocardial infarction, angina pectoris, heart failure and mild to moderate hypertension. May be used to treat supraventricular and tachyarrhythmias and as prophylaxis for migraine headaches.
• Pharmacology: Metoprolol, a competitive, beta1-selective (cardioselective) adrenergic antagonist, is similar to atenolol in its moderate lipid solubility, lack of intrinsic sympathomimetic activity (ISA), and weak membrane stabilizing activity (MSA).
• Toxicity: LD₅₀=5500 mg/kg (orally in rats), toxic effects include bradycardia, hypotension, bronchospasm, and cardiac failure. LD₅₀=2090 mg/kg (orally in mice)
• Affected Organisms: Humans and other mammals
• Biotransformation: Primarily hepatic
• Absorption: Rapid and complete, 50%
• Half Life: 3-7 hours
• Protein Binding: 12%
• Elimination: Less than 5% of an oral dose of metoprolol is recovered unchanged in the urine; the rest is excreted by the kidneys as metabolites that appear to have no beta-blocking activity.
• References: : Effect of metoprolol CR/XL in chronic heart failure: Metoprolol CR/XL Randomised Intervention Trial in Congestive Heart Failure (MERIT-HF) Lancet. 1999 Jun 12;353(9169):2001-7. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• : Effect of metoprolol CR/XL in chronic heart failure: Metoprolol CR/XL Randomised Intervention Trial in Congestive Heart Failure (MERIT-HF) Lancet. 1999 Jun 12;353(9169):2001-7. Pubmed