Esmolol

HCID 59768

Basic information

CAS
103598-03-4
Standard SMILES
COC(=O)CCc1ccc(OCC(O)CNC(C)C)cc1
InChIKey
AQNDDEOPVVGCPG-UHFFFAOYSA-N
Molecular formula
C16H25NO4
Average molar mass
295.37 g/mol
Monoisotopic mass
295.17835828

Overview

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.

Names & identifiers

Preferred name
Esmolol
IUPAC
methyl 3-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]propanoate
English name
ESMOLOL
Molecular formula
C16H25NO4
Molecular weight
295.37

Names & synonyms

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
Show more names
ESMOLOL USP/EP/BPMethyl 3-[4-[2-hydroxy-3-(isopropylamino)propoxy]phenyl]propionateMethyl 3-(4-(2-hydroxy-3-(isopropylaMino)propoxy)phenyl)propanoate hydrochlorideMethyl 3-{4-[2-Hydroxy-3-(isopropylamino)propoxy]phenyl}propanoate hydrochloride (Esmolol HCl)
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

Database identifiers

CAS
103598-03-4、81147-92-4
PubChem CID
59768
DTXSID
DTXSID4022995
ChEMBL
CHEMBL768
ChEBI
CHEBI:88206
UNII
MDY902UXSR
Nikkaji
J32.840E

Properties

Computed structural properties

XLogP
1.9
Topological polar surface area
67.8 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
5
Rotatable bonds
10
Heavy atoms
21

Experimental & physicochemical properties

Drugs · 2 items

Pharmaceuticals

Pharmaceuticals -> Antihypertensives

LogP1.7
Solubility · 2 items

Very soluble as hydrochloride salt

1.44e-01 g/L

Human Drugs · 2 items

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

Pharmaceuticals

Physical DescriptionSolid

Physicochemical properties

Melting point
48 · 48-50°C
Density
1.026 · 1.026
FDA UNII
902 UXSR · MDY902UXSR
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
319 · H319-H335-H315

Safety & regulation

Toxicology

Hepatotoxicity · 1 item

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 items

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

Safety data

Signal word
Warning
Symbol(GHS)
GHS07
Hazard statements
H319-H335-H315
Precautionary statements
P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P

Chemistry & industry

Pharmacology

ATC Code · 3 items

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 item

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 item

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 items

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.

Uses & manufacturing

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

Applications

UsesAnti-adrenergic (β-receptor).

Suppliers42 total

北京华美互利生物化工010-56205725 · [email protected]
Hebei Zhuanglai Chemical Trading Co Ltd+86-16264648883 · [email protected]
江苏正大丰海制药有限公司025-57033246-8069 17305112672 · [email protected]
湖北海克斯生化有限公司17362916295; 17362916295 · [email protected]
江苏艾康生物医药研发有限公司025-66061636 19370895928 · [email protected]
Additional notes · 1 item

DefinitionChEBI: 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 an aromatic ether, a member of ethanolamines, a methyl ester, 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.

Related reactions

2 records

Compound notes

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