Esmolol

HCID 178769322CAS 84057-94-3

Grundinformationen

Standard-SMILES
COC(=O)CCc1ccc(OCC(O)CNC(C)C)cc1
InChIKey
AQNDDEOPVVGCPG-UHFFFAOYSA-N
Summenformel
C16H25NO4
Durchschnittliche Molmasse
295,37 g/mol

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
Esmolol
IUPAC
methyl 3-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]propanoate
Englischer Name
esmolol
Summenformel
C16H25NO4
Molmasse
295.374

Namen und Synonyme

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
Weitere Namen anzeigen
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

Datenbank-Bezeichner

CAS
84057-94-3
ChEMBL
CHEMBL768
ChEBI
CHEBI:88206
UNII
MDY902UXSR
Nikkaji
J32.840E

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,9
Polarare Oberfläche (TPSA)
67,8 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
10
Schwere Atome
21

Experimentelle und physikochemische Eigenschaften

Drugs · 2 Einträge

Pharmaceuticals -> Antihypertensives

Pharmaceuticals

LogP1.7
Solubility · 2 Einträge

Very soluble as hydrochloride salt

1.44e-01 g/L

Human Drugs · 2 Einträge

Breast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Adrenergic Beta-Antagonists; Antiarrhythmics

Pharmaceuticals

Physical DescriptionSolid

Sicherheit und Regulatorisches

Toxikologische Informationen

Hepatotoxicity · 1 Eintrag

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 · 6 Einträge

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

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 3 Einträge

C07AB09

C - Cardiovascular system

QC - Cardiovascular system

Protein Binding55% bound to human plasma protein, while the acid metabolite is 10% bound.
Mechanism of Action · 1 Eintrag

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 · 1 Eintrag

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 · 5 Einträge

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.

Verwendung und Herstellung

UsesUse (kg; approx.) in Germany (2009): >10
Use ClassificationPharmaceuticals

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