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Identification
NameEsmolol
Accession NumberDB00187  (APRD00954)
TypeSmall Molecule
GroupsApproved
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 stabilizing 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.

Structure
Thumb
Synonyms
(±)-esmolol
(±)-methyl p-(2-hydroxy-3-(isopropylamino)propoxy)hydrocinnamate
3-[4-(2-Hydroxy-3-isopropylamino-propoxy)-phenyl]-propionic acid methyl ester
Methyl 4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)benzenepropanoate
methyl p-(2-hydroxy-3-(isopropylamino)propoxy)hydrocinnamate
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Breviblocinjection, solution10 mg/mLintravenousGeneral Injectables & Vaccines2010-07-01Not applicableUs
Breviblocinjection10 mg/mLintravenousBaxter Healthcare Corporation1986-12-31Not applicableUs
Breviblocinjection20 mg/mLintravenousBaxter Healthcare Corporation1986-12-31Not applicableUs
Breviblocinjection10 mg/mLintravenousBaxter Healthcare Corporation1986-12-31Not applicableUs
Brevibloc Injection 10mg/mlsolution10 mgintravenousBaxter Corporation1996-08-16Not applicableCanada
Brevibloc Injection 250mg/mlliquid250 mgintravenousBaxter Corporation1997-01-172007-06-27Canada
Brevibloc Liq IV 10mg/mlliquid10 mgintravenousOhmeda Pharmaceutical Products, Division Of Boc Canada Limited1994-12-311996-09-26Canada
Brevibloc Liq IV 250mg/mlliquid250 mgintravenousOhmeda Pharmaceutical Products, Division Of Boc Canada Limited1994-12-311997-08-25Canada
Brevibloc Premixed Injectionsolution10 mgintravenousBaxter Corporation2008-09-12Not applicableCanada
Esmololinjection10 mg/mLintravenousGeneral Injectables & Vaccines, Inc2010-04-01Not applicableUs
Esmolol Hydrochlorideinjection10 mg/mLintravenousWest Ward Pharmaceutical Corporation1986-12-31Not applicableUs
Esmolol Hydrochlorideinjection10 mg/mLintravenousCardinal Health1986-12-31Not applicableUs
Esmolol Hydrochlorideinjection10 mg/mLintravenousBaxter Healthcare Corporation1986-12-31Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Esmolol Hydrochlorideinjection, solution10 mg/mLintravenousAmerican Regent, Inc.2016-01-01Not applicableUs
Esmolol Hydrochlorideinjection, solution10 mg/mLintravenousMylan Institutional LLC2013-02-21Not applicableUs
Esmolol Hydrochlorideinjection, solution10 mg/mLintravenousFresenius Kabi USA, LLC2004-11-30Not applicableUs
Esmolol Hydrochlorideinjection, solution100 mg/10mLintravenousAuro Medics Pharma Llc2015-07-23Not applicableUs
Esmolol Hydrochlorideinjection10 mg/mLintravenousGeneral Injectables & Vaccines, Inc2012-06-13Not applicableUs
Esmolol Hydrochlorideinjection10 mg/mLintravenousGeneral Injectables & Vaccines, Inc2010-08-01Not applicableUs
Esmolol Hydrochlorideinjection10 mg/mLintravenousGENERAL INJECTABLES AND VACCINES, INC.2015-09-10Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Esmolol hydrochloride
81161-17-3
Thumb
  • InChI Key: GEKNCWBANDDJJL-UHFFFAOYSA-N
  • Monoisotopic Mass: 331.155036032
  • Average Mass: 331.835
DBSALT000586
Categories
UNIIMDY902UXSR
CAS number81147-92-4
WeightAverage: 295.374
Monoisotopic: 295.178358293
Chemical FormulaC16H25NO4
InChI KeyInChIKey=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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenol ethers
Direct ParentPhenol ethers
Alternative Parents
Substituents
  • Phenol ether
  • Fatty acid ester
  • Alkyl aryl ether
  • Fatty acyl
  • Methyl ester
  • Secondary alcohol
  • Carboxylic acid ester
  • 1,2-aminoalcohol
  • Secondary amine
  • Monocarboxylic acid or derivatives
  • Ether
  • Secondary aliphatic amine
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor 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.
PharmacodynamicsNot Available
Mechanism of actionSimilar 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.
Related Articles
AbsorptionRapidly 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 distributionNot Available
Protein binding55% bound to human plasma protein, while the acid metabolite is 10% bound.
Metabolism

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.

SubstrateEnzymesProduct
Esmolol
Not Available
MethanolDetails
Route of eliminationConsistent 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 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.
Clearance
  • 20 L/kg/hr [Men]
ToxicitySymptoms of overdose include cardiac arrest, bradycardia, hypotension, electromechanical dissociation and loss of consciousness.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Esmolol Action PathwayDrug actionSMP00301
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
Manufacturers
  • Baxter healthcare corp anesthesia critical care
  • App pharmaceuticals llc
  • Bedford laboratories
  • Bioniche pharma usa llc
Packagers
Dosage forms
FormRouteStrength
Injectionintravenous20 mg/mL
Solutionintravenous10 mg
Liquidintravenous10 mg
Liquidintravenous250 mg
Injectionintravenous10 mg/mL
Injection, solutionintravenous10 mg/mL
Injection, solutionintravenous100 mg/10mL
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)
CA2410446 No2008-08-262022-01-02Canada
US6310094 Yes2001-07-122021-07-12Us
US6528540 Yes2001-07-122021-07-12Us
Properties
StateSolid
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

DrugSyn.org

US4593119
General ReferencesNot Available
External Links
ATC CodesC07AB09
AHFS Codes
  • 24:24.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (56.3 KB)
Interactions
Drug Interactions
Drug
AcebutololEsmolol may increase the bradycardic activities of Acebutolol.
AcepromazineAcepromazine may increase the hypotensive activities of Esmolol.
AcetylcholineThe risk or severity of adverse effects can be increased when Esmolol is combined with Acetylcholine.
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Esmolol.
AlfuzosinEsmolol may increase the orthostatic hypotensive activities of Alfuzosin.
AmifostineEsmolol may increase the hypotensive activities of Amifostine.
AminophyllineEsmolol may decrease the activities of Aminophylline.
AmiodaroneAmiodarone may increase the bradycardic activities of Esmolol.
ArformoterolEsmolol may decrease the activities of Arformoterol.
AtenololEsmolol may increase the bradycardic activities of Atenolol.
BendroflumethiazideEsmolol may increase the bradycardic activities of Bendroflumethiazide.
BeractantEsmolol may increase the bradycardic activities of Beractant.
BetaxololEsmolol may increase the bradycardic activities of Betaxolol.
BisoprololEsmolol may increase the bradycardic activities of Bisoprolol.
BretyliumBretylium may increase the bradycardic activities of Esmolol.
BrimonidineBrimonidine may increase the antihypertensive activities of Esmolol.
BupivacaineThe serum concentration of Bupivacaine can be increased when it is combined with Esmolol.
ButabarbitalThe serum concentration of Esmolol can be decreased when it is combined with Butabarbital.
ButethalThe serum concentration of Esmolol can be decreased when it is combined with Butethal.
CabergolineEsmolol may increase the vasoconstricting activities of Cabergoline.
CalfactantEsmolol may increase the bradycardic activities of Calfactant.
CarbacholThe risk or severity of adverse effects can be increased when Esmolol is combined with Carbachol.
CarteololEsmolol may increase the bradycardic activities of Carteolol.
CarvedilolEsmolol may increase the bradycardic activities of Carvedilol.
CeritinibEsmolol may increase the bradycardic activities of Ceritinib.
ChloroquineThe metabolism of Esmolol can be decreased when combined with Chloroquine.
ChlorpropamideEsmolol may increase the hypoglycemic activities of Chlorpropamide.
ClonidineEsmolol may increase the bradycardic activities of Clonidine.
CrizotinibEsmolol may increase the bradycardic activities of Crizotinib.
DexmedetomidineEsmolol may increase the bradycardic activities of Dexmedetomidine.
DiazoxideDiazoxide may increase the hypotensive activities of Esmolol.
DigoxinEsmolol may increase the bradycardic activities of Digoxin.
DiltiazemEsmolol may increase the bradycardic activities of Diltiazem.
DipivefrinDipivefrin may increase the atrioventricular blocking (AV block) activities of Esmolol.
DipyridamoleDipyridamole may increase the bradycardic activities of Esmolol.
DisopyramideDisopyramide may increase the bradycardic activities of Esmolol.
DonepezilEsmolol may increase the bradycardic activities of Donepezil.
DronedaroneDronedarone may increase the bradycardic activities of Esmolol.
DuloxetineEsmolol may increase the orthostatic hypotensive activities of Duloxetine.
DyphyllineEsmolol may decrease the activities of Dyphylline.
FenoterolEsmolol may decrease the activities of Fenoterol.
FingolimodEsmolol may increase the bradycardic activities of Fingolimod.
FloctafenineThe risk or severity of adverse effects can be increased when Floctafenine is combined with Esmolol.
Fluticasone PropionateEsmolol may decrease the activities of Fluticasone Propionate.
FormoterolEsmolol may decrease the activities of Formoterol.
GalantamineEsmolol may increase the bradycardic activities of Galantamine.
GuanfacineEsmolol may increase the bradycardic activities of Guanfacine.
HeptabarbitalThe serum concentration of Esmolol can be decreased when it is combined with Heptabarbital.
HexobarbitalThe serum concentration of Esmolol can be decreased when it is combined with Hexobarbital.
IndacaterolEsmolol may decrease the activities of Indacaterol.
InfliximabInfliximab may decrease the antihypertensive activities of Esmolol.
Ipratropium bromideEsmolol may decrease the activities of Ipratropium bromide.
IvabradineEsmolol may increase the bradycardic activities of Ivabradine.
LabetalolEsmolol may increase the bradycardic activities of Labetalol.
LacosamideEsmolol may increase the atrioventricular blocking (AV block) activities of Lacosamide.
LanreotideEsmolol may increase the bradycardic activities of Lanreotide.
LevobunololEsmolol may increase the bradycardic activities of Levobunolol.
LevodopaEsmolol may increase the orthostatic hypotensive activities of Levodopa.
LidocaineThe serum concentration of Lidocaine can be increased when it is combined with Esmolol.
LucinactantEsmolol may increase the bradycardic activities of Lucinactant.
MepivacaineThe serum concentration of Mepivacaine can be increased when it is combined with Esmolol.
MethacholineThe risk or severity of adverse effects can be increased when Esmolol is combined with Methacholine.
MethohexitalThe serum concentration of Esmolol can be decreased when it is combined with Methohexital.
MethyldopaEsmolol may increase the bradycardic activities of Methyldopa.
MethylphenidateMethylphenidate may decrease the antihypertensive activities of Esmolol.
MetipranololEsmolol may increase the bradycardic activities of Metipranolol.
MetoprololEsmolol may increase the bradycardic activities of Metoprolol.
MidodrineEsmolol may increase the bradycardic activities of Midodrine.
MolsidomineMolsidomine may increase the hypotensive activities of Esmolol.
MoxonidineMoxonidine may increase the hypotensive activities of Esmolol.
NadololEsmolol may increase the bradycardic activities of Nadolol.
NebivololEsmolol may increase the bradycardic activities of Nebivolol.
NicorandilNicorandil may increase the hypotensive activities of Esmolol.
NifedipineNifedipine may increase the hypotensive activities of Esmolol.
ObinutuzumabEsmolol may increase the hypotensive activities of Obinutuzumab.
OctreotideEsmolol may increase the bradycardic activities of Octreotide.
OlodaterolEsmolol may decrease the activities of Olodaterol.
OrciprenalineEsmolol may decrease the activities of Orciprenaline.
PasireotideEsmolol may increase the bradycardic activities of Pasireotide.
PenbutololEsmolol may increase the bradycardic activities of Penbutolol.
PentobarbitalThe serum concentration of Esmolol can be decreased when it is combined with Pentobarbital.
PentoxifyllinePentoxifylline may increase the hypotensive activities of Esmolol.
PhenelzinePhenelzine may increase the orthostatic hypotensive activities of Esmolol.
PindololEsmolol may increase the bradycardic activities of Pindolol.
PirbuterolEsmolol may decrease the activities of Pirbuterol.
Poractant alfaEsmolol may increase the bradycardic activities of Poractant alfa.
PrazosinEsmolol may increase the orthostatic hypotensive activities of Prazosin.
PrimidoneThe serum concentration of Esmolol can be decreased when it is combined with Primidone.
PropafenoneThe serum concentration of Esmolol can be increased when it is combined with Propafenone.
PropranololEsmolol may increase the bradycardic activities of Propranolol.
QuinineQuinine may increase the hypotensive activities of Esmolol.
RegorafenibRegorafenib may increase the bradycardic activities of Esmolol.
ReserpineReserpine may increase the hypotensive activities of Esmolol.
RisperidoneEsmolol may increase the hypotensive activities of Risperidone.
RituximabEsmolol may increase the hypotensive activities of Rituximab.
RivastigmineRivastigmine may increase the bradycardic activities of Esmolol.
RuxolitinibRuxolitinib may increase the bradycardic activities of Esmolol.
SalbutamolEsmolol may decrease the activities of Salbutamol.
SalmeterolEsmolol may decrease the activities of Salmeterol.
SecobarbitalThe serum concentration of Esmolol can be decreased when it is combined with Secobarbital.
SotalolEsmolol may increase the bradycardic activities of Sotalol.
SufentanilSufentanil may increase the bradycardic activities of Esmolol.
TacrineTacrine may increase the bradycardic activities of Esmolol.
TadalafilTadalafil may increase the antihypertensive activities of Esmolol.
TerbutalineEsmolol may decrease the activities of Terbutaline.
TheophyllineEsmolol may decrease the activities of Theophylline.
TimololEsmolol may increase the bradycardic activities of Timolol.
TizanidineEsmolol may increase the bradycardic activities of Tizanidine.
TofacitinibTofacitinib may increase the bradycardic activities of Esmolol.
TranylcypromineTranylcypromine may increase the orthostatic hypotensive activities of Esmolol.
TreprostinilTreprostinil may increase the hypotensive activities of Esmolol.
ValsartanThe risk or severity of adverse effects can be increased when Valsartan is combined with Esmolol.
VardenafilVardenafil may increase the antihypertensive activities of Esmolol.
VerapamilEsmolol may increase the bradycardic activities of Verapamil.
VilanterolEsmolol may decrease the activities of Vilanterol.
YohimbineYohimbine may decrease the antihypertensive activities of Esmolol.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
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 equal affinity. Mediates Ras activation through G(s)-alpha- and cAMP-mediated signaling.
Gene Name:
ADRB1
Uniprot ID:
P08588
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 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on May 31, 2016 03:27