Record Information
Version1.0
Creation date2011-09-21 00:18:55 UTC
Update date2015-10-09 22:31:18 UTC
Primary IDFDB022742
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAtenolol
DescriptionAtenolol is a so-called beta1-selective (or 'cardioselective') drug. That means that it exerts greater blocking activity on myocardial beta1-receptors than on beta2 ones in the lung. The beta2 receptors are responsible to keep the bronchial system open. If these receptors are blocked, bronchospasm with serious lack of oxygen in the body can result. However, due to its cardioselective properties, the risk of bronchospastic reactions if using atenolol is reduced compared to nonselective drugs as propranolol. Nonetheless, this reaction may also be encountered with atenolol, particularly with high doses. Extreme caution should be exerted if atenolol is given to asthma patients, who are particularly at risk; the dose should be as low as possible. If an asthma attack occurs, the inhalation of a beta2-mimetic antiasthmatic, such as hexoprenalin or salbutamol, will usually suppress the symptoms.; Atenolol (trade name Tenormin) can be used to treat cardiovascular diseases such as hypertension, coronary heart disease, arrhythmias, and treatment of myocardial infarction after the acute event. Patients with compensated congestive heart failure may be treated with atenolol as a co medication (usually together with an ACE inhibitor, a diuretic and a digitalis-glycoside, if indicated). In patients with congestive heart failure, it reduces the need for and the consumption of oxygen of the heart muscle. It is very important to start with low doses, as atenolol reduces also the muscular power of the heart, which is an undesired effect in congestive heart failure. [HMDB]
CAS Number29122-68-7
Structure
Thumb
Synonyms
SynonymSource
1-p-Carbamoylmethylphenoxy-3-isopropylamino-2-propanolChEBI
2-(p-(2-Hydroxy-3-(isopropylamino)propoxy)phenyl)acetamideChEBI
4-(2-Hydroxy-3-((1-methylethyl)amino)propoxy)benzeneacetamideChEBI
AtenololumChEBI
TenorminKegg
AircritHMDB
AlinorHMDB
AltolHMDB
AnselolHMDB
AntipressanHMDB
Apo-atenololHMDB
AtcardilHMDB
AtecardHMDB
AtehexalHMDB
AtenblockHMDB
AtendolHMDB
AtenetHMDB
AteniHMDB
AtenilHMDB
Atenol 1a pharmaHMDB
Atenol acisHMDB
Atenol alHMDB
Atenol atidHMDB
Atenol copharHMDB
Atenol CTHMDB
Atenol fecofarHMDB
Atenol gadorHMDB
Atenol genericonHMDB
Atenol GNRHMDB
Atenol heumannHMDB
Atenol MSDHMDB
Atenol NM pharmaHMDB
Atenol nordicHMDB
Atenol PBHMDB
Atenol quesadaHMDB
Atenol stadaHMDB
Atenol tikaHMDB
Atenol tromHMDB
Atenol von CTHMDB
Atenol-mephaHMDB
Atenol-ratiopharmHMDB
Atenol-wolffHMDB
AtenolinHMDB
AtenomelHMDB
AterealHMDB
AterolHMDB
BetablokHMDB
BetacardHMDB
BetasynHMDB
Betatop geHMDB
BlocotenolHMDB
BlokiumHMDB
CardaxenHMDB
CardiopressHMDB
CorotenolHMDB
CuxanormHMDB
DuraatenololHMDB
DuratenolHMDB
EvitocorHMDB
FarnorminHMDB
Felo-bitsHMDB
HipresHMDB
HypotenHMDB
IbinoloHMDB
InternololHMDB
JenatenolHMDB
JuventalHMDB
Lo-tenHMDB
LotenHMDB
LotenalHMDB
MyocordHMDB
NormalolHMDB
NormitenHMDB
NotenHMDB
OradayHMDB
OrmidolHMDB
PanapresHMDB
PlenacorHMDB
PremorineHMDB
PrenololHMDB
PrenormineHMDB
PrinormHMDB
Scheinpharm atenolHMDB
Seles betaHMDB
SeloblocHMDB
SertenHMDB
ServitenolHMDB
SterminHMDB
TenidonHMDB
TenoblocHMDB
TenoblockHMDB
TenololHMDB
TenoprinHMDB
TenoreticHMDB
TenormineHMDB
TensiminHMDB
TredolHMDB
UniblocHMDB
UnilocHMDB
VascotenHMDB
VericordinHMDB
WesipinHMDB
XatenHMDB
1-P-Carbamoylmethylphenoxy-3-isopropylamino-2-propanolChEBI
2-(P-(2-Hydroxy-3-(isopropylamino)propoxy)phenyl)acetamideChEBI
Apo-Atenololhmdb
Atenol 1A pharmahmdb
Atenol ALhmdb
Atenol Atidhmdb
Atenol Copharhmdb
Atenol cthmdb
Atenol Fecofarhmdb
Atenol Gadorhmdb
Atenol Genericonhmdb
Atenol Heumannhmdb
Atenol NM Pharmahmdb
Atenol Nordichmdb
Atenol Quesadahmdb
Atenol Stadahmdb
Atenol Tikahmdb
Atenol Tromhmdb
Atenol von cthmdb
Atenol-Mephahmdb
Atenol-Wolffhmdb
Atenolol (JAN/USP)hmdb
Atenolol [USAN:BAN:INN:JAN]hmdb
Atenololum [INN-Latin]hmdb
Betatop Gehmdb
duratenolhmdb
Felo-Bitshmdb
Scheinpharm Atenolhmdb
Tenormin (TN)hmdb
Tenormine [French]hmdb
Predicted Properties
PropertyValueSource
Water Solubility0.43 g/LALOGPS
logP0.57ALOGPS
logP0.43ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)14.08ChemAxon
pKa (Strongest Basic)9.67ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area84.58 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity73.51 m³·mol⁻¹ChemAxon
Polarizability29.98 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC14H22N2O3
IUPAC name2-(4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)acetamide
InChI IdentifierInChI=1S/C14H22N2O3/c1-10(2)16-8-12(17)9-19-13-5-3-11(4-6-13)7-14(15)18/h3-6,10,12,16-17H,7-9H2,1-2H3,(H2,15,18)
InChI KeyMETKIMKYRPQLGS-UHFFFAOYSA-N
Isomeric SMILESCC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1
Average Molecular Weight266.3361
Monoisotopic Molecular Weight266.16304258
Classification
Description Belongs to the class of organic compounds known as phenylacetamides. These are amide derivatives of phenylacetic acids.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetamides
Direct ParentPhenylacetamides
Alternative Parents
Substituents
  • Phenylacetamide
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • 1,2-aminoalcohol
  • Amino acid or derivatives
  • Carboxamide group
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Carboxylic acid derivative
  • Secondary amine
  • Secondary aliphatic amine
  • Ether
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Route of exposure:

Biological location:

Role

Environmental role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-00e9-9000000000-6a38697da7945fdb1908Spectrum
Predicted GC-MSAtenolol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0kmi-8920000000-75c70fad839dc47116bfSpectrum
Predicted GC-MSAtenolol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05fr-9451000000-8069c1e0c4bc41c41dc5Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0uy0-0950000000-e882b8032954e2a624cfSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0076-4920000000-3c7f23b7695e5c4dcc4cSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0aos-9800000000-93a18f0e030605aa10aaSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0002-3910000000-43ae37638a8827ea76f1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01b9-6980000000-3a2af9caa0ddc645756aSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0290000000-0e1f60f7eeef06627206Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0900000000-dda902f75e8d8e525d4fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0900000000-32b90aea04b68bdedbefSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0900000000-f333c3bfc9bd6c0593d4Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004l-0890000000-5c0a8df3cdde41f290f2Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0090000000-58fd12e8cca5ee837799Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0090000000-271732f56fff3c9ecf87Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014l-3960000000-ee2e8e341081d16f5fdbSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-006t-3900000000-ff916216d2f4fc373c18Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-007k-3900000000-7ce05e231c161678a1d9Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a5a-4900000000-4d9ba2cbcfaa9a4fd7fcSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0090000000-326ded7fdf97f0b34fc5Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0090000000-bb7e0317c8b0c0a5abbcSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014l-3960000000-7c774d4cb55b5368392aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-1190000000-9c46f6de428fd9c85b0cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-5490000000-d3676c10983a2bf51eb7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-9400000000-f879d668e69afad6eb16Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1590000000-21fbf983e89a88c8fda0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-2910000000-55258981df3fe8b9c9edSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9500000000-fc86b722c900f0c12c6fSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID2162
ChEMBL IDCHEMBL24
KEGG Compound IDC13235
Pubchem Compound ID2249
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB00335
HMDB IDHMDB01924
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAtenolol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Beta-1 adrenergic receptorADRB1P08588
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference