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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2017-10-23 19:06:15 UTC
HMDB IDHMDB0014333
Secondary Accession Numbers
  • HMDB14333
Metabolite Identification
Common NameEsmolol
DescriptionEsmolol (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.
Structure
Thumb
Synonyms
ValueSource
BreviblocMeSH
Esmolol hydrochlorideMeSH
Chemical FormulaC16H25NO4
Average Molecular Weight295.374
Monoisotopic Molecular Weight295.178358293
IUPAC Namemethyl 3-(4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)propanoate
Traditional Nameesmolol
CAS Registry Number103598-03-4
SMILES
COC(=O)CCC1=CC=C(OCC(O)CNC(C)C)C=C1
InChI Identifier
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
InChI KeyAQNDDEOPVVGCPG-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassPhenol ethers
Direct ParentPhenol ethers
Alternative Parents
Substituents
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Fatty acid ester
  • Monocyclic benzene moiety
  • Fatty acyl
  • Methyl ester
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Secondary amine
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Secondary aliphatic amine
  • Ether
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Amine
  • Organic nitrogen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.14 g/LNot Available
LogP1.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity81.05 m³·mol⁻¹ChemAxon
Polarizability33.68 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fk9-9630000000-d551ff7db097920ee10aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-4912000000-8428bd5b9c71bba4b8e3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-0490000000-55cd388bbf570d69d195View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-1190000000-7d08c97e98a5d306d8daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-8590000000-da4f55d9275617bd6402View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-9500000000-08aa89fd1914ce6a579dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1590000000-c5f36e8382810e69c6aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01r2-1900000000-6a2e2bd7c87493c461a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-2900000000-fc3c798f1e113b4150ccView in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Esmolol PathwayPw000369Pw000369 greyscalePw000369 simpleNot Available
Displaying 1 entry
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00187 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00187 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00187
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID53916
KEGG Compound IDC06980
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEsmolol
METLIN IDNot Available
PubChem Compound59768
PDB IDNot Available
ChEBI ID4856
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
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
Gene Name:
ADRB1
Uniprot ID:
P08588
Molecular weight:
51322.1
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 ]