methyl 3-(4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)propanoate

• ChemBase编号: 72
• 分子式: C16H25NO4
• 平均质量: 295.374
• 单一同位素质量: 295.17835829
• SMILES: O(CC(O)CNC(C)C)c1ccc(CCC(=O)OC)cc1
• Canonical SMILES: COC(=O)CCc1ccc(cc1)OCC(CNC(C)C)O
• InChI: InChI=1S/C16H25NO4/c1-12(2)17-10-14(18)11-21-15-7-4-13(5-8-15)6-9-16(19)20-3/h4-5,7-8,12,14,17-18H,6,9-11H2,1-3H3
• InChIKey: AQNDDEOPVVGCPG-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: methyl 3-(4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)propanoate
• IUPAC传统名: esmolol
• 商标名: Brevibloc; Esmolol HCL; Esmolol Hydrochloride
• 别名: Esmolol

登记号

• CAS号: 103598-03-4
• PubChem SID: 160963535; 46506146
• PubChem CID: 59768
• CHEBI ID: 4856
• ATC码: C07AB09
• CHEMBL: 768
• Chemspider ID: 53916
• DrugBank ID: DB00187
• KEGG ID: D07916
• 美国药典/FDA物质标识码: MDY902UXSR
• 维基百科标题: Esmolol

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): -1.3708016
• LogD (pH = 7.4): -0.4028085
• Log P: 1.8224301
• 摩尔折射率: 81.0532 cm^3
• 极化性: 32.33148 Å^3
• 极化表面积: 67.79 Å^2
• 可自由旋转的化学键: 10
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.02
• LOG S: -3.31
• 溶解度: 1.44e-01 g/l

分子性质

理化性质

• 溶解度: Very soluble as hydrochloride salt
• 疏水性(logP): 1.7

药理学性质

• 给药途径: iv
• 生物利用度: -
• 排泄: Renal
• 半衰期: 9 minutes
• 代谢: Erythrocytic
• 蛋白结合率: 60%
• 妊娠期药物分类: C (Australia); C (US)

详细说明

DrugBank - DB00187

• Drug Groups: approved
• Description: Esmolol (trade name Brevibloc) is a cardioselective beta1 receptor blocker with rapid onset, a very short duration of action, and no significant intrinsic sympathomimetic or membrane stabilising activity at therapeutic dosages.; ; Esmolol decreases the force and rate of heart contractions by blocking beta-adrenergic receptors of the sympathetic nervous system, which are found in the heart and other organs of the body. Esmolol prevents the action of two naturally occurring substances: epinephrine and norepinephrine.
• Indication: For the rapid control of ventricular rate in patients with atrial fibrillation or atrial flutter in perioperative, postoperative, or other emergent circumstances where short term control of ventricular rate with a short-acting agent is desirable. Also used in noncompensatory sinus tachycardia where the rapid heart rate requires specific intervention.
• Toxicity: Symptoms of overdose include cardiac arrest, bradycardia, hypotension, electromechanical dissociation and loss of consciousness.
• Affected Organisms: Humans and other mammals
• Biotransformation: Rapidly metabolized by hydrolysis of the ester linkage, chiefly by the esterases in the cytosol of red blood cells and not by plasma cholinesterases or red cell membrane acetylcholinesterase. Mainly in red blood cells to a free acid metabolite (with 1/1500 the activity of esmolol) and methanol.
• Absorption: Rapidly absorbed, steady-state blood levels for dosages from 50-300 µg/kg/min (0.05-0.3 mg/kg/mm) are obtained within five minutes.
• Half Life: Rapid 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.
• Protein Binding: 55% bound to human plasma protein, while the acid metabolite is 10% bound.
• Elimination: Consistent with the high rate of blood-based metabolism of esmolol hydrochloride, less than 2% of the drug is excreted unchanged in the urine. The acid metabolite has an elimination half-life of about 3.7 hours and is excreted in the urine with a clearance approximately equivalent to the glomerular filtration rate. ; Excretion of the acid metabolite is significantly decreased in patients with renal disease, with the elimination half-life increased to about ten-fold that of normals, and plasma levels considerably elevated.
• Clearance: * 20 L/kg/hr [Men]
• External Links: Wikipedia; RxList; Drugs.com