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Record Information
Version3.6
Creation Date2006-05-18 08:50:34 UTC
Update Date2016-02-11 01:05:07 UTC
HMDB IDHMDB01932
Secondary Accession NumbersNone
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
Thumb
Synonyms
ValueSource
(RS)-MetoprololChEBI
1-(isopropylamino)-3-[4-(2-Methoxyethyl)phenoxy]propan-2-olChEBI
(+/-)-metoprololHMDB
BeatrololHMDB
DL-MetoprololHMDB
LopresorHMDB
LopresoreticHMDB
LopressorHMDB
MeijoprololHMDB
MetohexalHMDB
Metoprolol succinateHMDB
Metoprolol tartrateHMDB
MetoprololumHMDB
PreblokHMDB
PresololHMDB
SelokenHMDB
SerokenHMDB
SpesicorHMDB
Toprol-XLHMDB
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 Name1-(isopropylamino)-3-[4-(2-methoxyethyl)phenoxy]propan-2-ol
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 KeyInChIKey=IUBSYMUCCVWXPE-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as tyrosols and derivatives. These are compounds containing a hydroxyethyl group attached to the C4 carbon of a phenol group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenols and derivatives
Direct ParentTyrosols and derivatives
Alternative Parents
Substituents
  • Tyrosol derivative
  • Phenol ether
  • Alkyl aryl ether
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Secondary amine
  • Ether
  • Secondary aliphatic amine
  • Dialkyl ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Drug
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.88HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.4 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity76.7 m3·mol-1ChemAxon
Polarizability31.9 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0v0c-3248359000-0353ef81c3bc6d7fcfd5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-014l-2514911000-b5f7785723f1eaf61e6fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-05ir-1729351100-fb362124379cb4616c5eView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Metoprolol PathwaySMP00302Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.071 +/- 0.0076 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022749
KNApSAcK IDNot Available
Chemspider ID4027
KEGG Compound IDC07202
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMetoprolol
NuGOwiki LinkHMDB01932
Metagene LinkHMDB01932
METLIN ID1250
PubChem Compound4171
PDB IDNot Available
ChEBI ID6904
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. [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. [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. [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