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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:35 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
Data?1582753166
Synonyms
ValueSource
BreviblocHMDB
Esmolol hydrochlorideHMDB
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
Description 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
ClassPhenol ethers
Sub ClassNot Available
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
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.14 g/LNot Available
LogP1.7Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+170.94531661259
DarkChem[M-H]-170.33231661259
DeepCCS[M+H]+171.44430932474
DeepCCS[M-H]-169.08630932474
DeepCCS[M-2H]-201.97230932474
DeepCCS[M+Na]+177.53730932474
AllCCS[M+H]+173.532859911
AllCCS[M+H-H2O]+170.532859911
AllCCS[M+NH4]+176.332859911
AllCCS[M+Na]+177.132859911
AllCCS[M-H]-174.032859911
AllCCS[M+Na-2H]-174.832859911
AllCCS[M+HCOO]-175.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
EsmololCOC(=O)CCC1=CC=C(OCC(O)CNC(C)C)C=C13107.9Standard polar33892256
EsmololCOC(=O)CCC1=CC=C(OCC(O)CNC(C)C)C=C12243.6Standard non polar33892256
EsmololCOC(=O)CCC1=CC=C(OCC(O)CNC(C)C)C=C12264.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Esmolol,1TMS,isomer #1COC(=O)CCC1=CC=C(OCC(CNC(C)C)O[Si](C)(C)C)C=C12274.3Semi standard non polar33892256
Esmolol,1TMS,isomer #2COC(=O)CCC1=CC=C(OCC(O)CN(C(C)C)[Si](C)(C)C)C=C12404.3Semi standard non polar33892256
Esmolol,2TMS,isomer #1COC(=O)CCC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C12458.8Semi standard non polar33892256
Esmolol,2TMS,isomer #1COC(=O)CCC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C12477.4Standard non polar33892256
Esmolol,2TMS,isomer #1COC(=O)CCC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C12797.9Standard polar33892256
Esmolol,1TBDMS,isomer #1COC(=O)CCC1=CC=C(OCC(CNC(C)C)O[Si](C)(C)C(C)(C)C)C=C12508.3Semi standard non polar33892256
Esmolol,1TBDMS,isomer #2COC(=O)CCC1=CC=C(OCC(O)CN(C(C)C)[Si](C)(C)C(C)(C)C)C=C12664.1Semi standard non polar33892256
Esmolol,2TBDMS,isomer #1COC(=O)CCC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C12921.6Semi standard non polar33892256
Esmolol,2TBDMS,isomer #1COC(=O)CCC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C12884.5Standard non polar33892256
Esmolol,2TBDMS,isomer #1COC(=O)CCC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C12985.2Standard polar33892256
Spectra
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00187 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00187 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00187
Phenol Explorer Compound IDNot Available
FooDB 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 ID88206
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]