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51384-51-1 分子结构
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{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和InChIs

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

引用这个纪录

CBID:149 http://www.chembase.cn/molecule-149.html

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名称和登记号

名称和登记号

名称 登记号
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
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

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID 价格

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 14.087972  质子受体
质子供体 LogD (pH = 5.5) -1.4345746 
LogD (pH = 7.4) -0.46658155  Log P 1.7586571 
摩尔折射率 76.6976 cm3 极化性 30.335455 Å3
极化表面积 50.72 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 1.8  LOG S -2.82 
溶解度 4.02e-01 g/l 

分子性质

分子性质

理化性质 药理学性质 生物活性(PubChem)
溶解度
16.9 mg/mL expand 查看数据来源
熔点
120°C (248°F) expand 查看数据来源
疏水性(logP)
1.6 expand 查看数据来源
给药途径
Oral, IV expand 查看数据来源
生物利用度
12% expand 查看数据来源
排泄
Renal expand 查看数据来源
半衰期
3-7 hours expand 查看数据来源
代谢
Hepatic via CYP2D6, CYP3A4 expand 查看数据来源
法定药品分级
Rx-only expand 查看数据来源
妊娠期药物分类
C (Australia) expand 查看数据来源
C (US) expand 查看数据来源
美国(FDA)药品许可证
Metoprolol expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Wikipedia Wikipedia
DrugBank -  DB00264 external link
Item Information
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

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • : 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
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专利

专利

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