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Record Information
Version3.6
Creation Date2006-05-18 08:35:03 UTC
Update Date2016-02-11 01:05:07 UTC
HMDB IDHMDB01924
Secondary Accession NumbersNone
Metabolite Identification
Common 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.
Structure
Thumb
Synonyms
ValueSource
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
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
TenorminHMDB
TenormineHMDB
TensiminHMDB
TredolHMDB
UniblocHMDB
UnilocHMDB
VascotenHMDB
VericordinHMDB
WesipinHMDB
XatenHMDB
Chemical FormulaC14H22N2O3
Average Molecular Weight266.3361
Monoisotopic Molecular Weight266.16304258
IUPAC Name2-(4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)acetamide
Traditional Nameatenolol
CAS Registry Number29122-68-7
SMILES
CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1
InChI Identifier
InChI=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 KeyInChIKey=METKIMKYRPQLGS-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Phenol ether
  • Alkyl aryl ether
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Carboxamide group
  • 1,2-aminoalcohol
  • Secondary amine
  • Ether
  • Secondary aliphatic amine
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Drug
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point147 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility13.3 mg/mL at 25 °CNot Available
LogP0.16HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.43 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity73.51 m3·mol-1ChemAxon
Polarizability29.98 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, Positive (Annotated)splash10-0uy0-0950000000-e882b8032954e2a624cfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0076-4920000000-3c7f23b7695e5c4dcc4cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0aos-9800000000-93a18f0e030605aa10aaView in MoNA
MSMass Spectrum (Electron Ionization)splash10-00e9-9000000000-6a38697da7945fdb1908View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Atenolol PathwaySMP00298Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified3.75 (0.037-7.5) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-2 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
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 IDFDB022742
KNApSAcK IDNot Available
Chemspider ID2162
KEGG Compound IDC13235
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAtenolol
NuGOwiki LinkHMDB01924
Metagene LinkHMDB01924
METLIN ID1128
PubChem Compound2249
PDB IDNot Available
ChEBI ID2904
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

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