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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-18 08:35:03 UTC
Update Date2021-09-14 15:46:28 UTC
HMDB IDHMDB0001924
Secondary Accession Numbers
  • HMDB01924
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
Data?1582752217
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
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
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 KeyMETKIMKYRPQLGS-UHFFFAOYSA-N
Chemical Taxonomy
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
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular 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)
Experimental Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
DeepCCS[M+H]+CBM159.530932474
AllCCS[M+H]+Not Available158.962http://allccs.zhulab.cn/database/detail?ID=AllCCS00000777
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.43 g/LALOGPS
logP10(0.57) g/LALOGPS
logP10(0.43) g/LChemAxon
logS10(-2.8) g/LALOGPS
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
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+163.56831661259
DarkChem[M-H]-161.40431661259
AllCCS[M+H]+164.25432859911
AllCCS[M-H]-165.96932859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Atenolol,1TMS,#1CC(C)NCC(COC1=CC=C(CC(N)=O)C=C1)O[Si](C)(C)C2406.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Atenolol,1TMS,#2CC(C)NCC(O)COC1=CC=C(CC(=O)N[Si](C)(C)C)C=C12460.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Atenolol,1TMS,#3CC(C)N(CC(O)COC1=CC=C(CC(N)=O)C=C1)[Si](C)(C)C2516.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Atenolol,1TBDMS,#1CC(C)NCC(COC1=CC=C(CC(N)=O)C=C1)O[Si](C)(C)C(C)(C)C2650.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Atenolol,1TBDMS,#2CC(C)NCC(O)COC1=CC=C(CC(=O)N[Si](C)(C)C(C)(C)C)C=C12668.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Atenolol,1TBDMS,#3CC(C)N(CC(O)COC1=CC=C(CC(N)=O)C=C1)[Si](C)(C)C(C)(C)C2755.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Atenolol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kmi-8920000000-75c70fad839dc47116bf2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Atenolol GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-9451000000-8069c1e0c4bc41c41dc52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Atenolol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Atenolol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Atenolol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-00e9-9000000000-6a38697da7945fdb19082014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Atenolol Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0uy0-0950000000-e882b8032954e2a624cf2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atenolol Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0076-4920000000-3c7f23b7695e5c4dcc4c2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atenolol Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0aos-9800000000-93a18f0e030605aa10aa2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atenolol LC-ESI-qTof , Positive-QTOFsplash10-0002-3910000000-43ae37638a8827ea76f12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atenolol LC-ESI-QTOF , positive-QTOFsplash10-01b9-6980000000-3a2af9caa0ddc645756a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atenolol LC-ESI-QTOF , positive-QTOFsplash10-014i-0290000000-0e1f60f7eeef066272062017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atenolol LC-ESI-QTOF , positive-QTOFsplash10-0002-0900000000-dda902f75e8d8e525d4f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atenolol LC-ESI-QTOF , positive-QTOFsplash10-0002-0900000000-32b90aea04b68bdedbef2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atenolol LC-ESI-QTOF , positive-QTOFsplash10-0002-0900000000-f333c3bfc9bd6c0593d42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atenolol LC-ESI-ITFT , positive-QTOFsplash10-004l-0890000000-5c0a8df3cdde41f290f22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atenolol LC-ESI-ITFT , positive-QTOFsplash10-014i-0090000000-58fd12e8cca5ee8377992017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atenolol LC-ESI-ITFT , positive-QTOFsplash10-014i-0090000000-271732f56fff3c9ecf872017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atenolol LC-ESI-ITFT , positive-QTOFsplash10-014l-3960000000-ee2e8e341081d16f5fdb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atenolol LC-ESI-ITFT , positive-QTOFsplash10-006t-3900000000-ff916216d2f4fc373c182017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atenolol LC-ESI-ITFT , positive-QTOFsplash10-007k-3900000000-7ce05e231c161678a1d92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atenolol LC-ESI-ITFT , positive-QTOFsplash10-0a5a-4900000000-4d9ba2cbcfaa9a4fd7fc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atenolol LC-ESI-ITFT , positive-QTOFsplash10-014i-0090000000-326ded7fdf97f0b34fc52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atenolol LC-ESI-ITFT , positive-QTOFsplash10-014i-0090000000-bb7e0317c8b0c0a5abbc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atenolol LC-ESI-ITFT , positive-QTOFsplash10-014l-3960000000-7c774d4cb55b5368392a2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Atenolol 10V, Positive-QTOFsplash10-0gb9-1190000000-9c46f6de428fd9c85b0c2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Atenolol 20V, Positive-QTOFsplash10-00di-5490000000-d3676c10983a2bf51eb72017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Atenolol 40V, Positive-QTOFsplash10-05fr-9400000000-f879d668e69afad6eb162017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Atenolol 10V, Negative-QTOFsplash10-014i-1590000000-21fbf983e89a88c8fda02017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Atenolol 20V, Negative-QTOFsplash10-0zfr-2910000000-55258981df3fe8b9c9ed2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Atenolol 40V, Negative-QTOFsplash10-0006-9500000000-fc86b722c900f0c12c6f2017-07-26Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified3.75 (0.037-7.5) uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00335
Phenol Explorer Compound IDNot Available
FooDB IDFDB022742
KNApSAcK IDNot Available
Chemspider ID2162
KEGG Compound IDC13235
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAtenolol
METLIN ID1128
PubChem Compound2249
PDB IDNot Available
ChEBI ID2904
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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