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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-18 08:50:34 UTC
Update Date2022-03-07 02:49:11 UTC
HMDB IDHMDB0001932
Secondary Accession Numbers
  • HMDB01932
Metabolite Identification
Common NameMetoprolol
DescriptionMetoprolol is a selective beta1 receptor blocker used in treatment of several diseases of the cardiovascular system. It is marketed under the brand name Lopressor by Novartis, and Toprol (in the USA); Seleken or Selokeen (elsewhere); A selective adrenergic beta-1-blocking agent with no stimulatory action. It's binding to plasma albumin is weaker than alprenolol and it may be useful in the treatment of several diseases of the cardiovascular system; Metoprolol is a selective beta1 receptor blocker used in treatment of several diseases of the cardiovascular system. It is marketed under the brand name Lopressor by Novartis, and Toprol (in the USA); Seleken or Selokeen (elsewhere); as Minax by Alphapharm (in Australia), as Betaloc by AstraZeneca and as Corvitol by Berlin-Chemie AG; A selective adrenergic beta-1-blocking agent with no stimulatory action. It's binding to plasma albumin is weaker than alprenolol and it may be useful in angina pectoris, hypertension, or cardiac arrhythmias; as Minax by Alphapharm (in Australia), as Betaloc by AstraZeneca and as Corvitol by Berlin-Chemie AG.
Structure
Data?1582752217
Synonyms
ValueSource
(RS)-MetoprololChEBI
1-(Isopropylamino)-3-[4-(2-methoxyethyl)phenoxy]propan-2-olChEBI
(+/-)-metoprololHMDB
BeatrololHMDB
DL-MetoprololHMDB
LopresorHMDB
LopresoreticHMDB
LopressorHMDB, MeSH
MeijoprololHMDB
MetohexalHMDB
Metoprolol succinateHMDB, MeSH
Metoprolol tartrateHMDB, MeSH
MetoprololumHMDB
PreblokHMDB
PresololHMDB
SelokenHMDB, MeSH
SerokenHMDB
SpesicorHMDB, MeSH
Toprol-XLHMDB, MeSH
Beloc durilesMeSH, HMDB
Beloc-durilesMeSH, HMDB
BetalocMeSH, HMDB
Succinate, metoprololMeSH, HMDB
ToprolMeSH, HMDB
BelocDurilesMeSH, HMDB
Betaloc astraMeSH, HMDB
CR-XL, MetoprololMeSH, HMDB
SpesikorMeSH, HMDB
Tartrate, metoprololMeSH, HMDB
Toprol XLMeSH, HMDB
Metoprolol CR-XLMeSH, HMDB
Betaloc-astraMeSH, HMDB
BetalokMeSH, HMDB
Metoprolol CR XLMeSH, HMDB
ToprolXLMeSH, HMDB
BetalocAstraMeSH, HMDB
Chemical FormulaC15H25NO3
Average Molecular Weight267.3639
Monoisotopic Molecular Weight267.183443671
IUPAC Name1-[4-(2-methoxyethyl)phenoxy]-3-[(propan-2-yl)amino]propan-2-ol
Traditional Namemetoprolol
CAS Registry Number37350-58-6
SMILES
COCCC1=CC=C(OCC(O)CNC(C)C)C=C1
InChI Identifier
InChI=1S/C15H25NO3/c1-12(2)16-10-14(17)11-19-15-6-4-13(5-7-15)8-9-18-3/h4-7,12,14,16-17H,8-11H2,1-3H3
InChI KeyIUBSYMUCCVWXPE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tyrosols and derivatives. Tyrosols and derivatives are compounds containing a hydroxyethyl group attached to the C4 carbon of a phenol group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassTyrosols and derivatives
Direct ParentTyrosols and derivatives
Alternative Parents
Substituents
  • Tyrosol derivative
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Dialkyl ether
  • Secondary amine
  • Secondary aliphatic amine
  • Ether
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.88HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM172.730932474
[M+H]+Not Available170.692http://allccs.zhulab.cn/database/detail?ID=AllCCS00000730
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.4 g/LALOGPS
logP1.8ALOGPS
logP1.76ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)14.09ChemAxon
pKa (Strongest Basic)9.67ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area50.72 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity76.7 m³·mol⁻¹ChemAxon
Polarizability31.9 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]+163.9231661259
DarkChem[M-H]-164.14631661259
AllCCS[M+H]+166.87332859911
AllCCS[M-H]-168.40832859911
DeepCCS[M+H]+166.87730932474
DeepCCS[M-H]-164.51930932474
DeepCCS[M-2H]-197.40530932474
DeepCCS[M+Na]+172.9730932474
AllCCS[M+H]+166.932859911
AllCCS[M+H-H2O]+163.632859911
AllCCS[M+NH4]+169.932859911
AllCCS[M+Na]+170.732859911
AllCCS[M-H]-168.432859911
AllCCS[M+Na-2H]-169.232859911
AllCCS[M+HCOO]-170.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MetoprololCOCCC1=CC=C(OCC(O)CNC(C)C)C=C12639.5Standard polar33892256
MetoprololCOCCC1=CC=C(OCC(O)CNC(C)C)C=C12011.3Standard non polar33892256
MetoprololCOCCC1=CC=C(OCC(O)CNC(C)C)C=C12028.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Metoprolol,1TMS,isomer #1COCCC1=CC=C(OCC(CNC(C)C)O[Si](C)(C)C)C=C12063.1Semi standard non polar33892256
Metoprolol,1TMS,isomer #2COCCC1=CC=C(OCC(O)CN(C(C)C)[Si](C)(C)C)C=C12204.3Semi standard non polar33892256
Metoprolol,2TMS,isomer #1COCCC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C12253.9Semi standard non polar33892256
Metoprolol,2TMS,isomer #1COCCC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C12252.4Standard non polar33892256
Metoprolol,2TMS,isomer #1COCCC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C12473.2Standard polar33892256
Metoprolol,1TBDMS,isomer #1COCCC1=CC=C(OCC(CNC(C)C)O[Si](C)(C)C(C)(C)C)C=C12293.9Semi standard non polar33892256
Metoprolol,1TBDMS,isomer #2COCCC1=CC=C(OCC(O)CN(C(C)C)[Si](C)(C)C(C)(C)C)C=C12457.9Semi standard non polar33892256
Metoprolol,2TBDMS,isomer #1COCCC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C12709.8Semi standard non polar33892256
Metoprolol,2TBDMS,isomer #1COCCC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C12642.0Standard non polar33892256
Metoprolol,2TBDMS,isomer #1COCCC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C12685.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Metoprolol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-7920000000-15359015d85b4c565e862017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Metoprolol GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9122000000-12f9e089d37951143a412017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Metoprolol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Metoprolol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Metoprolol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Metoprolol GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Metoprolol GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Metoprolol Quattro_QQQ 10V, N/A-QTOF (Annotated)splash10-0v0c-3248359000-0353ef81c3bc6d7fcfd52012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metoprolol Quattro_QQQ 25V, N/A-QTOF (Annotated)splash10-014l-2514911000-b5f7785723f1eaf61e6f2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metoprolol Quattro_QQQ 40V, N/A-QTOF (Annotated)splash10-05ir-1729351100-fb362124379cb4616c5e2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metoprolol LC-ESI-QTOF , positive-QTOFsplash10-01b9-9760000000-90ea4861dda115391e262017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metoprolol LC-ESI-ITFT , positive-QTOFsplash10-014l-0920000000-b7c75fc96ea4b12a1f402017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metoprolol LC-ESI-ITFT , positive-QTOFsplash10-014i-0090000000-5e678ec3b5c3302abb3c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metoprolol LC-ESI-ITFT , positive-QTOFsplash10-014i-0190000000-0ea5b7fc1dda907b176b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metoprolol LC-ESI-ITFT , positive-QTOFsplash10-01b9-4940000000-5e4d95fb248589c9af912017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metoprolol LC-ESI-ITFT , positive-QTOFsplash10-05gi-4900000000-73204756032f7604c22e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metoprolol LC-ESI-ITFT , positive-QTOFsplash10-05fr-4900000000-597c5d64a09cf1b8f88d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metoprolol LC-ESI-ITFT , positive-QTOFsplash10-0zml-5900000000-ca840796f27bfcb3bd0f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metoprolol LC-ESI-ITFT , positive-QTOFsplash10-014i-0090000000-9ae9e49826b05fa823f52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metoprolol LC-ESI-ITFT , positive-QTOFsplash10-014i-0190000000-cfdea758641b8b5c956e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metoprolol LC-ESI-ITFT , positive-QTOFsplash10-01b9-3940000000-248e03350c5dfe8e13022017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metoprolol LC-ESI-ITFT , positive-QTOFsplash10-05gi-4900000000-24d3886dc7605253aeb82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metoprolol LC-ESI-ITFT , positive-QTOFsplash10-05gi-4900000000-08c6d3455af24f523db22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metoprolol LC-ESI-ITFT , positive-QTOFsplash10-0zmi-5900000000-9b22afca158afbaeb6d12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metoprolol LC-ESI-ITFT , positive-QTOFsplash10-014l-0920000000-851dcbef33e79ed226432017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metoprolol LC-ESI-QTOF , positive-QTOFsplash10-014i-0090000000-61bef9702ed80c36d1072017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metoprolol 10V, Positive-QTOFsplash10-014i-1290000000-e429d824fc6518e2de0f2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metoprolol 20V, Positive-QTOFsplash10-00xr-9870000000-6859dfe077cd63365e3b2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metoprolol 40V, Positive-QTOFsplash10-00di-9500000000-84deaf041eadbd4d3ea22017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metoprolol 10V, Negative-QTOFsplash10-0gb9-1790000000-1fa6e9e32d3d6f058f892017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metoprolol 20V, Negative-QTOFsplash10-0udi-1900000000-0545f16ae4bdd137d91e2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metoprolol 40V, Negative-QTOFsplash10-0ldr-3900000000-cfffc2daf6eda94b4e602017-07-26Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
Tissue Locations
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.071 +/- 0.0076 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4027
KEGG Compound IDC07202
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMetoprolol
METLIN IDNot Available
PubChem Compound4171
PDB IDNot Available
ChEBI ID6904
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferencePalmer, Sven; Sidenqvist, Michael. Process for the preparation of metoprolol. PCT Int. Appl. (1998), 12 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Bauer LA, Horn JR, Maxon MS, Easterling TR, Shen DD, Strandness DE Jr: Effect of metoprolol and verapamil administered separately and concurrently after single doses on liver blood flow and drug disposition. J Clin Pharmacol. 2000 May;40(5):533-43. [PubMed:10806607 ]
  2. Murthy SS, Shetty HU, Nelson WL, Jackson PR, Lennard MS: Enantioselective and diastereoselective aspects of the oxidative metabolism of metoprolol. Biochem Pharmacol. 1990 Oct 1;40(7):1637-44. [PubMed:2222517 ]
  3. Chaturvedi AK, Smith DR, Canfield DV: A fatality caused by accidental production of hydrogen sulfide. Forensic Sci Int. 2001 Dec 1;123(2-3):211-4. [PubMed:11728749 ]

Enzymes

General function:
Involved in monooxygenase 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 antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
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