Identification

Name
Esmolol
Accession Number
DB00187
Description

Esmolol, commonly marketed under the trade name Brevibloc, is a cardioselective beta-1 receptor blocker. It has a rapid onset but short duration of action without causing significant intrinsic sympathomimetic or membrane stabilizing activities at recommended therapeutic doses. It works by blocking beta-adrenergic receptors in the heart, which leads to decreased force and rate of heart contractions. Esmolol prevents the action of two naturally occurring substances: epinephrine and norepinephrine.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 295.374
Monoisotopic: 295.178358293
Chemical Formula
C16H25NO4
Synonyms
  • (±)-esmolol
  • (±)-methyl p-(2-hydroxy-3-(isopropylamino)propoxy)hydrocinnamate
  • 3-[4-(2-Hydroxy-3-isopropylamino-propoxy)-phenyl]-propionic acid methyl ester
  • Esmolol
  • Methyl 4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)benzenepropanoate
  • methyl p-(2-hydroxy-3-(isopropylamino)propoxy)hydrocinnamate

Pharmacology

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.

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics
Not Available
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.

TargetActionsOrganism
ABeta-1 adrenergic receptor
antagonist
Humans
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.

Volume of distribution
Not Available
Protein binding

55% bound to human plasma protein, while the acid metabolite is 10% bound.

Metabolism

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.

Hover over products below to view reaction partners

Route of 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.

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.

Clearance
  • 20 L/kg/hr [Men]
Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity

Symptoms of overdose include cardiac arrest, bradycardia, hypotension, electromechanical dissociation and loss of consciousness.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Esmolol Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbataceptThe metabolism of Esmolol can be increased when combined with Abatacept.
AbirateroneThe metabolism of Esmolol can be decreased when combined with Abiraterone.
AcebutololEsmolol may increase the arrhythmogenic activities of Acebutolol.
AceclofenacAceclofenac may decrease the antihypertensive activities of Esmolol.
AcemetacinAcemetacin may decrease the antihypertensive activities of Esmolol.
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Esmolol.
AcetohexamideEsmolol may increase the hypoglycemic activities of Acetohexamide.
AcetophenazineThe serum concentration of Esmolol can be increased when it is combined with Acetophenazine.
AcetylcholineThe risk or severity of adverse effects can be increased when Esmolol is combined with Acetylcholine.
AcetyldigitoxinEsmolol may increase the arrhythmogenic activities of Acetyldigitoxin.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
No interactions found.

Products

Product Ingredients
IngredientUNIICASInChI Key
Esmolol hydrochlorideV05260LC8D81161-17-3GEKNCWBANDDJJL-UHFFFAOYSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BreviblocInjection10 mg/1mLIntravenousBaxter Healthcare Corporation1986-12-31Not applicableUS flag
BreviblocInjection20 mg/1mLIntravenousBaxter Healthcare Corporation2007-03-022007-03-02US flag
BreviblocInjection10 mg/1mLIntravenousBaxter Healthcare Corporation1986-12-31Not applicableUS flag
BreviblocInjection20 mg/1mLIntravenousBaxter Healthcare Corporation1986-12-31Not applicableUS flag
BreviblocInjection20 mg/1mLIntravenousBaxter Healthcare Corporation1986-12-31Not applicableUS flag
BreviblocInjection, solution, concentrate250 mg/1mLIntravenousBaxter Healthcare Corporation2007-03-022007-03-02US flag
BreviblocInjection10 mg/1mLIntravenousGeneral Injectables & Vaccines2010-07-01Not applicableUS flag
BreviblocInjection20 mg/1mLIntravenousBaxter Healthcare Corporation1986-12-31Not applicableUS flag
BreviblocInjection10 mg/1mLIntravenousBaxter Healthcare Corporation1986-12-31Not applicableUS flag
BreviblocInjection10 mg/1mLIntravenousBaxter Healthcare Corporation1986-12-31Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Esmolol HydrochlorideInjection, solution10 mg/1mLIntravenousFresenius Kabi USA, LLC2004-11-30Not applicableUS flag
Esmolol HydrochlorideInjection, solution10 mg/1mLIntravenousGeneral Injectables & Vaccines2012-06-132017-07-01US flag
Esmolol HydrochlorideInjection, solution10 mg/1mLIntravenousAMERICAN REGENT, INC.2016-01-012016-02-01US flag
Esmolol HydrochlorideInjection, solution100 mg/10mLIntravenousGeneral Injectables and Vaccines, Inc.2018-09-20Not applicableUS flag
Esmolol HydrochlorideInjection, solution100 mg/10mLIntravenousA-S Medication Solutions2015-07-23Not applicableUS flag
Esmolol HydrochlorideInjection, solution100 mg/10mLIntravenousHF Acquisition Co LLC, DBA HealthFirst2019-12-22Not applicableUS flag
Esmolol HydrochlorideInjection, solution10 mg/1mLIntravenousMylan Teoranta2013-05-092013-05-10US flag
Esmolol HydrochlorideInjection, solution20 mg/1mLIntravenousSagent Pharmaceuticals2019-07-15Not applicableUS flag
Esmolol HydrochlorideInjection, solution10 mg/1mLIntravenousSagent Pharmaceuticals2020-01-15Not applicableUS flag
Esmolol HydrochlorideInjection, solution10 mg/1mLIntravenousBedford Pharmaceuticals2004-10-042014-09-30US flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories

ATC Codes
C07AB09 — Esmolol
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenol ethers
Sub Class
Not Available
Direct Parent
Phenol ethers
Alternative Parents
Phenoxy compounds / Fatty acid esters / Alkyl aryl ethers / Methyl esters / Secondary alcohols / Amino acids and derivatives / 1,2-aminoalcohols / Monocarboxylic acids and derivatives / Dialkylamines / Organopnictogen compounds
show 3 more
Substituents
1,2-aminoalcohol / Alcohol / Alkyl aryl ether / Amine / Amino acid or derivatives / Aromatic homomonocyclic compound / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Ether
show 17 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
aromatic ether, secondary alcohol, secondary amino compound, methyl ester, ethanolamines (CHEBI:4856)

Chemical Identifiers

UNII
MDY902UXSR
CAS number
81147-92-4
InChI Key
AQNDDEOPVVGCPG-UHFFFAOYSA-N
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
IUPAC Name
methyl 3-(4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)propanoate
SMILES
COC(=O)CCC1=CC=C(OCC(O)CNC(C)C)C=C1

References

Synthesis Reference
US4593119
General References
Not Available
Human Metabolome Database
HMDB0014333
KEGG Drug
D07916
KEGG Compound
C06980
PubChem Compound
59768
PubChem Substance
46506146
ChemSpider
53916
BindingDB
50404796
RxNav
49737
ChEBI
88206
ChEMBL
CHEMBL768
Therapeutic Targets Database
DAP000304
PharmGKB
PA449500
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Esmolol
AHFS Codes
  • 24:24.00 — Beta-adrenergic Blocking Agents
MSDS
Download (56.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceOverdose of Beta-adrenergic Blocking Drug / Overdose, Drug1
4CompletedPreventionPostoperative pain1
4CompletedPreventionSurgery, Cardiac1
4CompletedPreventionSurgery, Laparoscopic1
4CompletedSupportive CareInjection Site Irritation1
4CompletedTreatmentAnesthesia; Adverse Effect / Reflex, Abnormal / Tinnitus, Spontaneous Oto-Acoustic Emission1
4CompletedTreatmentGall Stone Disease1
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Myocardial Ischemia / Tachycardia1
4Not Yet RecruitingOtherAtrial Fibrillation (AF)1
4Not Yet RecruitingPreventionIntraoperative Awareness / Postoperative pain1

Pharmacoeconomics

Manufacturers
  • Baxter healthcare corp anesthesia critical care
  • App pharmaceuticals llc
  • Bedford laboratories
  • Bioniche pharma usa llc
Packagers
  • APP Pharmaceuticals
  • Baxter International Inc.
  • Bedford Labs
  • Ben Venue Laboratories Inc.
  • Bioniche Pharma
  • Bristol-Myers Squibb Co.
  • Draxis Specialty Pharmaceuticals Inc.
  • General Injectables and Vaccines Inc.
  • Paddock Labs
Dosage Forms
FormRouteStrength
InjectionIntravenous20 mg/1mL
Injection, solutionParenteral100 MG/10ML
Injection, solution, concentrateIntravenous250 mg/1mL
SolutionParenteral100 mg/10ml
Injection, solutionIntravenous10 mg/ml
SolutionIntravenous
LiquidIntravenous
Injection10 mg/ml
SolutionIntravenous10 mg/ml
Injection, solutionIntravenous20 mg/ml
Solution, concentrateIntravenous250 mg
Injection, powder, for solutionParenteral2500 MG
Injection, solution100 MG/10ML
InjectionIntravenous10 mg/1mL
Injection, solutionIntravenous10 mg/1mL
Injection, solutionIntravenous100 mg/10mL
Injection, solutionIntravenous20 mg/1mL
Injection, solutionParenteral10 MG/ML
Injection
Injection2500 mg/250ml
Prices
Unit descriptionCostUnit
Brevibloc 250 mg/ml ampul13.21USD ml
Brevibloc 10 mg/ml vial2.21USD ml
Brevibloc 20 mg/ml iv bag1.54USD ml
Esmolol hcl 10 mg/ml vial1.26USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
CA2410446No2008-08-262022-01-02Canada flag
US6528540Yes2003-03-042021-07-12US flag
US6310094Yes2001-10-302021-07-12US flag
US8835505No2014-09-162033-03-15US flag
US8829054No2014-09-092033-03-15US flag
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilityVery soluble as hydrochloride saltNot Available
logP1.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.144 mg/mLALOGPS
logP2.02ALOGPS
logP1.82ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)14.09ChemAxon
pKa (Strongest Basic)9.67ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area67.79 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity81.05 m3·mol-1ChemAxon
Polarizability33.68 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.7023
Blood Brain Barrier-0.9645
Caco-2 permeable+0.5
P-glycoprotein substrateSubstrate0.6511
P-glycoprotein inhibitor INon-inhibitor0.8625
P-glycoprotein inhibitor IINon-inhibitor0.7171
Renal organic cation transporterNon-inhibitor0.8605
CYP450 2C9 substrateNon-substrate0.8124
CYP450 2D6 substrateSubstrate0.663
CYP450 3A4 substrateNon-substrate0.5869
CYP450 1A2 substrateNon-inhibitor0.864
CYP450 2C9 inhibitorNon-inhibitor0.8789
CYP450 2D6 inhibitorNon-inhibitor0.8806
CYP450 2C19 inhibitorNon-inhibitor0.9585
CYP450 3A4 inhibitorNon-inhibitor0.8495
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9761
Ames testNon AMES toxic0.9066
CarcinogenicityNon-carcinogens0.9519
BiodegradationNot ready biodegradable0.6493
Rat acute toxicity1.9194 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9556
hERG inhibition (predictor II)Non-inhibitor0.774
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-0490000000-55cd388bbf570d69d195

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Receptor signaling protein activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...
Gene Name
ADRB1
Uniprot ID
P08588
Uniprot Name
Beta-1 adrenergic receptor
Molecular Weight
51322.1 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Jahn P, Eckrich B, Schneidrowski B, Volz-Zang C, Schulte B, Mutschler E, Palm D: Beta 1-adrenoceptor subtype selective antagonism of esmolol and its major metabolite in vitro and in man. Investigations using tricresylphosphate as red blood cell carboxylesterase inhibitor. Arzneimittelforschung. 1995 May;45(5):536-41. [PubMed:7612051]
  3. Volz-Zang C, Eckrich B, Jahn P, Schneidrowski B, Schulte B, Palm D: Esmolol, an ultrashort-acting, selective beta 1-adrenoceptor antagonist: pharmacodynamic and pharmacokinetic properties. Eur J Clin Pharmacol. 1994;46(5):399-404. [PubMed:7957532]
  4. Kirshenbaum JM: Nonthrombolytic intervention in acute myocardial infarction. Am J Cardiol. 1989 Jul 18;64(4):25B-28B. [PubMed:2568748]
  5. Jacobs JR, Maier GW, Rankin JS, Reves JG: Esmolol and left ventricular function in the awake dog. Anesthesiology. 1988 Mar;68(3):373-8. [PubMed:2894187]
  6. Howie MB, Black HA, Zvara D, McSweeney TD, Martin DJ, Coffman JA: Esmolol reduces autonomic hypersensitivity and length of seizures induced by electroconvulsive therapy. Anesth Analg. 1990 Oct;71(4):384-8. [PubMed:1975995]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Sternieri E, Coccia CP, Pinetti D, Guerzoni S, Ferrari A: Pharmacokinetics and interactions of headache medications, part II: prophylactic treatments. Expert Opin Drug Metab Toxicol. 2006 Dec;2(6):981-1007. doi: 10.1517/17425255.2.6.981 . [PubMed:17125412]
  2. Brodde OE, Kroemer HK: Drug-drug interactions of beta-adrenoceptor blockers. Arzneimittelforschung. 2003;53(12):814-22. [PubMed:14732961]
  3. Iwaki M, Niwa T, Bandoh S, Itoh M, Hirose H, Kawase A, Komura H: Application of substrate depletion assay to evaluation of CYP isoforms responsible for stereoselective metabolism of carvedilol. Drug Metab Pharmacokinet. 2016 Dec;31(6):425-432. doi: 10.1016/j.dmpk.2016.08.007. Epub 2016 Sep 2. [PubMed:27836712]

Drug created on June 13, 2005 07:24 / Updated on October 27, 2020 11:13

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