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

• ChemBase编号: 149
• 分子式: C15H25NO3
• 平均质量: 267.3639
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: {2-hydroxy-3-[4-(2-methoxyethyl)phenoxy]propyl}(propan-2-yl)amine
• IUPAC传统名: metoprolol
• 商标名: Beloc; Betaloc; Lopressor HCT; Lopresor; Lopresoretic; Lopressor; Metroprolol; Prelis; Selo-Zok; Seloken; Selopral; Toprol; Toprol-XL; Toprol XL; Lopressor, Toprol-xl
• 别名: Metoprolol Tartrate; Metoprolol succinate; Metoprolol

登记号

• CAS号: 51384-51-1; 37350-58-6
• PubChem SID: 46506211; 160963612
• PubChem CID: 4171
• CHEBI ID: 6904
• ATC码: C07AB02
• CHEMBL: 13
• Chemspider ID: 4027
• DrugBank ID: DB00264
• IUPHAR配体索引: 553
• KEGG ID: D02358
• 美国药典/FDA物质标识码: GEB06NHM23
• 维基百科标题: Metoprolol
• Medline Plus: a682864

理论计算性质

JChem

• Acid pKa: 14.087972
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): -1.4345746
• LogD (pH = 7.4): -0.46658155
• Log P: 1.7586571
• 摩尔折射率: 76.6976 cm^3
• 极化性: 30.335455 Å^3
• 极化表面积: 50.72 Å^2
• 可自由旋转的化学键: 9
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.8
• LOG S: -2.82
• 溶解度: 4.02e-01 g/l

分子性质

理化性质

• 溶解度: 16.9 mg/mL
• 熔点: 120°C (248°F)
• 疏水性(logP): 1.6

药理学性质

• 给药途径: Oral, IV
• 生物利用度: 12%
• 排泄: Renal
• 半衰期: 3-7 hours
• 代谢: Hepatic via CYP2D6, CYP3A4
• 法定药品分级: Rx-only
• 妊娠期药物分类: C (Australia); C (US)
• 美国（FDA）药品许可证: Metoprolol

详细说明

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

参考文献

• : 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