Showing Compound Metoprolol (FDB022749)

Record Information

Version

1.0

Creation date

2011-09-21 00:19:01 UTC

Update date

2018-05-28 18:33:54 UTC

Primary ID

FDB022749

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Metoprolol

Description

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); 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. [HMDB]

CAS Number

37350-58-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(RS)-Metoprolol	ChEBI
1-(Isopropylamino)-3-[4-(2-methoxyethyl)phenoxy]propan-2-ol	ChEBI
(+/-)-metoprolol	HMDB
Beatrolol	HMDB
DL-Metoprolol	HMDB
Lopresor	HMDB
Lopresoretic	HMDB
Lopressor	HMDB, MeSH
Meijoprolol	HMDB
Metohexal	HMDB
Metoprolol succinate	HMDB, MeSH
Metoprolol tartrate	HMDB, MeSH
Metoprololum	HMDB
Preblok	HMDB
Presolol	HMDB
Seloken	HMDB, MeSH
Seroken	HMDB
Spesicor	HMDB, MeSH
Toprol-XL	HMDB, MeSH
Beloc duriles	MeSH, HMDB
Beloc-duriles	MeSH, HMDB
Betaloc	MeSH, HMDB
Succinate, metoprolol	MeSH, HMDB
Toprol	MeSH, HMDB
BelocDuriles	MeSH, HMDB
Betaloc astra	MeSH, HMDB
CR-XL, Metoprolol	MeSH, HMDB
Spesikor	MeSH, HMDB
Tartrate, metoprolol	MeSH, HMDB
Toprol XL	MeSH, HMDB
Metoprolol CR-XL	MeSH, HMDB
Betaloc-astra	MeSH, HMDB
Betalok	MeSH, HMDB
Metoprolol CR XL	MeSH, HMDB
ToprolXL	MeSH, HMDB
BetalocAstra	MeSH, HMDB
(+/-)-Metoprolol	hmdb
dl-Metoprolol	hmdb
Metoprolol	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	0.4 g/L	ALOGPS
logP	1.8	ALOGPS
logP	1.76	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	14.09	ChemAxon
pKa (Strongest Basic)	9.67	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	50.72 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	76.7 m³·mol⁻¹	ChemAxon
Polarizability	31.9 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C15H25NO3

IUPAC name

1-[4-(2-methoxyethyl)phenoxy]-3-[(propan-2-yl)amino]propan-2-ol

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 Key

IUBSYMUCCVWXPE-UHFFFAOYSA-N

Isomeric SMILES

COCCC1=CC=C(OCC(O)CNC(C)C)C=C1

Average Molecular Weight

267.3639

Monoisotopic Molecular Weight

267.183443671

Classification

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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

Tyrosols and derivatives

Direct Parent

Tyrosols 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:6904 )
secondary alcohol (CHEBI:6904 )
secondary amino compound (CHEBI:6904 )
propanolamine (CHEBI:6904 )

Ontology

Disposition

Biological location:

Organ and components:

Liver

Subcellular:

Biofluid and excreta:

Role

Industrial application:

Drug

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Metoprolol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0udi-7920000000-15359015d85b4c565e86	Spectrum
Predicted GC-MS	Metoprolol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-9122000000-12f9e089d37951143a41	Spectrum
Predicted GC-MS	Metoprolol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Metoprolol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Metoprolol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Metoprolol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Metoprolol, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-0v0c-3248359000-0353ef81c3bc6d7fcfd5	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-014l-2514911000-b5f7785723f1eaf61e6f	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-05ir-1729351100-fb362124379cb4616c5e	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-01b9-9760000000-90ea4861dda115391e26	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-014l-0920000000-b7c75fc96ea4b12a1f40	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-014i-0090000000-5e678ec3b5c3302abb3c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-014i-0190000000-0ea5b7fc1dda907b176b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-01b9-4940000000-5e4d95fb248589c9af91	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-05gi-4900000000-73204756032f7604c22e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-05fr-4900000000-597c5d64a09cf1b8f88d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0zml-5900000000-ca840796f27bfcb3bd0f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-014i-0090000000-9ae9e49826b05fa823f5	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-014i-0190000000-cfdea758641b8b5c956e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-01b9-3940000000-248e03350c5dfe8e1302	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-05gi-4900000000-24d3886dc7605253aeb8	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-05gi-4900000000-08c6d3455af24f523db2	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0zmi-5900000000-9b22afca158afbaeb6d1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-014l-0920000000-851dcbef33e79ed22643	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0090000000-61bef9702ed80c36d107	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-1290000000-e429d824fc6518e2de0f	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00xr-9870000000-6859dfe077cd63365e3b	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9500000000-84deaf041eadbd4d3ea2	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0gb9-1790000000-1fa6e9e32d3d6f058f89	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-1900000000-0545f16ae4bdd137d91e	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ldr-3900000000-cfffc2daf6eda94b4e60	2017-07-26	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		Spectrum