基本情報
- CAS
84057-94-3- 標準SMILES
COC(=O)CCc1ccc(OCC(O)CNC(C)C)cc1- InChIKey
AQNDDEOPVVGCPG-UHFFFAOYSA-N- 分子式
- C16H25NO4
- 平均分子量
- 295.37 g/mol
概要
Methyl 3-{4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl}propanoate is a methyl ester that is methyl 3-(4-hydroxyphenyl)propanoate in which the hydrogen attached to the phenolic hydroxy group is substituted by a 2-hydroxy-3-(isopropylamino)propyl group. It is a member of ethanolamines, a methyl ester, an aromatic ether, a secondary alcohol and a secondary amino compound. It is functionally related to a 3-{4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl}propanoic acid.
名称と識別子
- 優先名称
- Esmolol
- IUPAC
- methyl 3-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]propanoate
- 英語名
- esmolol
- 分子式
- C16H25NO4
- 分子量
- 295.374
名称と別名
ESMOLOL81147-92-4(+-)-EsmololMDY902UXSRBenzenepropanoic acid, 4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)-, methyl esterASL-8052-001Methyl 4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)benzenepropanoateDTXSID4022995methyl 3-(4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)propanoatemethyl p-(2-hydroxy-3-(isopropylamino)propoxy)hydrocinnamateesmololummethyl 3-(4-(2-hydroxy-3-((propan-2-yl)amino)propoxy)phenyl)propanoate
名称をさらに表示
Brn 5287174
3-(4-(2-Hydroxy-3-isopropylamino-propoxy)-phenyl)-propionic acid methyl ester3-[4-(2-Hydroxy-3-isopropylamino-propoxy)-phenyl]-propionic acid methyl esterBenzenepropanoic acid, 4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]-, methyl esterRefChem:56563CHEBI:4856DTXCID702995C07AB09(+-)-methyl p-(2-hydroxy-3-(isopropylamino)propoxy)hydrocinnamate
データベース識別子
- CAS
84057-94-3- ChEMBL
CHEMBL768- ChEBI
物性
構造計算による物性
- XLogP
- 1.9
- 極性表面積
- 67.8 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 5
- 回転可能結合数
- 10
- 重原子数
- 21
- 形式電荷
- 0
- 複雑度
- 288
実験および物理化学的性質
Drugs
Pharmaceuticals -> Antihypertensives
Pharmaceuticals
LogP1.7
Solubility
Very soluble as hydrochloride salt
1.44e-01 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Adrenergic Beta-Antagonists; Antiarrhythmics
Pharmaceuticals
Physical DescriptionSolid
安全と法規制
毒性情報
Hepatotoxicity
Esmolol therapy has not been clearly associated with serum aminotransferase elevations or with clinically apparent, acute liver injury. It is often used in critically patients and generally for a short period only. Thus, hepatotoxicity due to esmolol must be very rare, if it occurs at all. Most commonly used beta-blockers have been linked to rare instances of clinically apparent liver injury, typically with onset within 2 to 12 weeks, a hepatocellular pattern of liver enzyme elevations, rapid recovery upon withdrawal, and little evidence of hypersensitivity (rash, fever, eosinophilia) or autoantibody formation. Similar instances have not been reported after esmolol use.
Adverse Effects* The most common adverse reaction with esmolol is hemodynamic compromise, which happens to over 10% of all patients.
Toxicity SummarySigns and Symptoms of Overdose
Drug Induced Liver Injury
Benchmark Dataset for the Liver Toxicity Knowledge Base (LTKB)
esmolol
Brevibloc®
Beta blockers
Not Applicable
no-DILI-concern
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
化学と産業
薬理情報
ATC Code
C07AB09
C - Cardiovascular system
QC - Cardiovascular system
Protein Binding55% bound to human plasma protein, while the acid metabolite is 10% bound.
Mechanism of Action
Similar to other beta-blockers, esmolol blocks the agonistic effect of the sympathetic neurotransmitters by competing for receptor binding sites. Because it predominantly blocks the beta-1 receptors in cardiac tissue, it is said to be cardioselective. In general, so-called cardioselective beta-blockers are relatively cardioselective; at lower doses they block beta-1 receptors only but begin to block beta-2 receptors as the dose increases. At therapeutic dosages, esmolol does not have intrinsic sympathomimetic activity (ISA) or membrane-stabilizing (quinidine-like) activity. Antiarrhythmic activity is due to blockade of adrenergic stimulation of cardiac pacemaker potentials. In the Vaughan Williams classification of antiarrhythmics, beta-blockers are considered to be class II agents.
Biological Half-LifeRapid distribution half-life of about 2 minutes and an elimination half-life of about 9 minutes. The acid metabolite has an elimination half-life of about 3.7 hours.
Metabolism/Metabolites
Esmolol undergoes rapid hydrolysis of ester linkage which is catalyzed by esterases found in the cytosol of red blood cells (RBCs). The plasma cholinersterases or RBC membrane acetylcholinesterases are not involved in this metabolic reaction. Metabolism of the drug occurs mainly in RBCs to form a free acid metabolite (with 1/1500 the activity of esmolol) and methanol.
FDA Pharmacological Classification
MDY902UXSR
ESMOLOL
Mechanisms of Action [MoA] - Adrenergic beta-Antagonists
Established Pharmacologic Class [EPC] - beta-Adrenergic Blocker
Esmolol is a beta-Adrenergic Blocker. The mechanism of action of esmolol is as an Adrenergic beta-Antagonist.
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