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Showing metabocard for Atenolol (HMDB0001924)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
enzymes (2) Show 2 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-18 08:35:03 UTC
Update Date2022-03-07 02:49:11 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
MOLSDFPDBSMILESInChI

MOL for HMDB0001924 (Atenolol)

Not Available

3D MOL for HMDB0001924 (Atenolol)

Not Available

3D SDF for HMDB0001924 (Atenolol)

Not Available

3D-SDF for HMDB0001924 (Atenolol)

Not Available

PDB for HMDB0001924 (Atenolol)

Not Available

3D PDB for HMDB0001924 (Atenolol)

Not Available

SMILES for HMDB0001924 (Atenolol)

Not Available

INCHI for HMDB0001924 (Atenolol)

Not Available
View in JSmolView Stereo Labels
SynonymsNot Available
Chemical FormulaC14H22N2O3
Average Molecular Weight266.3361
Monoisotopic Molecular Weight266.16304258
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number29122-68-7
SMILESNot Available
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
ClassificationNot classified
Ontology
Physiological effect
Health effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Industrial applicationEnvironmental role
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 Chromatographic Properties
Predicted Molecular PropertiesNot Available
Predicted Chromatographic Properties

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.2.58 minutes32390414
Predicted by Siyang on May 30, 20229.8334 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20225.35 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid226.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AtenololCC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C13618.1Standard polar33892256
AtenololCC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C12209.6Standard non polar33892256
AtenololCC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C12307.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Atenolol,1TMS,isomer #1CC(C)NCC(COC1=CC=C(CC(N)=O)C=C1)O[Si](C)(C)C2406.4Semi standard non polar33892256
Atenolol,1TMS,isomer #2CC(C)NCC(O)COC1=CC=C(CC(=O)N[Si](C)(C)C)C=C12460.4Semi standard non polar33892256
Atenolol,1TMS,isomer #3CC(C)N(CC(O)COC1=CC=C(CC(N)=O)C=C1)[Si](C)(C)C2516.8Semi standard non polar33892256
Atenolol,2TMS,isomer #1CC(C)NCC(COC1=CC=C(CC(=O)N[Si](C)(C)C)C=C1)O[Si](C)(C)C2437.3Semi standard non polar33892256
Atenolol,2TMS,isomer #1CC(C)NCC(COC1=CC=C(CC(=O)N[Si](C)(C)C)C=C1)O[Si](C)(C)C2403.4Standard non polar33892256
Atenolol,2TMS,isomer #1CC(C)NCC(COC1=CC=C(CC(=O)N[Si](C)(C)C)C=C1)O[Si](C)(C)C2851.2Standard polar33892256
Atenolol,2TMS,isomer #2CC(C)N(CC(COC1=CC=C(CC(N)=O)C=C1)O[Si](C)(C)C)[Si](C)(C)C2564.6Semi standard non polar33892256
Atenolol,2TMS,isomer #2CC(C)N(CC(COC1=CC=C(CC(N)=O)C=C1)O[Si](C)(C)C)[Si](C)(C)C2374.4Standard non polar33892256
Atenolol,2TMS,isomer #2CC(C)N(CC(COC1=CC=C(CC(N)=O)C=C1)O[Si](C)(C)C)[Si](C)(C)C3130.9Standard polar33892256
Atenolol,2TMS,isomer #3CC(C)N(CC(O)COC1=CC=C(CC(=O)N[Si](C)(C)C)C=C1)[Si](C)(C)C2556.4Semi standard non polar33892256
Atenolol,2TMS,isomer #3CC(C)N(CC(O)COC1=CC=C(CC(=O)N[Si](C)(C)C)C=C1)[Si](C)(C)C2523.2Standard non polar33892256
Atenolol,2TMS,isomer #3CC(C)N(CC(O)COC1=CC=C(CC(=O)N[Si](C)(C)C)C=C1)[Si](C)(C)C2968.8Standard polar33892256
Atenolol,2TMS,isomer #4CC(C)NCC(O)COC1=CC=C(CC(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C12526.1Semi standard non polar33892256
Atenolol,2TMS,isomer #4CC(C)NCC(O)COC1=CC=C(CC(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C12478.5Standard non polar33892256
Atenolol,2TMS,isomer #4CC(C)NCC(O)COC1=CC=C(CC(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C12958.4Standard polar33892256
Atenolol,3TMS,isomer #1CC(C)N(CC(COC1=CC=C(CC(=O)N[Si](C)(C)C)C=C1)O[Si](C)(C)C)[Si](C)(C)C2578.3Semi standard non polar33892256
Atenolol,3TMS,isomer #1CC(C)N(CC(COC1=CC=C(CC(=O)N[Si](C)(C)C)C=C1)O[Si](C)(C)C)[Si](C)(C)C2523.2Standard non polar33892256
Atenolol,3TMS,isomer #1CC(C)N(CC(COC1=CC=C(CC(=O)N[Si](C)(C)C)C=C1)O[Si](C)(C)C)[Si](C)(C)C2776.2Standard polar33892256
Atenolol,3TMS,isomer #2CC(C)NCC(COC1=CC=C(CC(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)O[Si](C)(C)C2474.2Semi standard non polar33892256
Atenolol,3TMS,isomer #2CC(C)NCC(COC1=CC=C(CC(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)O[Si](C)(C)C2509.0Standard non polar33892256
Atenolol,3TMS,isomer #2CC(C)NCC(COC1=CC=C(CC(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)O[Si](C)(C)C2721.9Standard polar33892256
Atenolol,3TMS,isomer #3CC(C)N(CC(O)COC1=CC=C(CC(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C2628.3Semi standard non polar33892256
Atenolol,3TMS,isomer #3CC(C)N(CC(O)COC1=CC=C(CC(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C2629.4Standard non polar33892256
Atenolol,3TMS,isomer #3CC(C)N(CC(O)COC1=CC=C(CC(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C2834.0Standard polar33892256
Atenolol,4TMS,isomer #1CC(C)N(CC(COC1=CC=C(CC(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)O[Si](C)(C)C)[Si](C)(C)C2660.8Semi standard non polar33892256
Atenolol,4TMS,isomer #1CC(C)N(CC(COC1=CC=C(CC(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)O[Si](C)(C)C)[Si](C)(C)C2634.0Standard non polar33892256
Atenolol,4TMS,isomer #1CC(C)N(CC(COC1=CC=C(CC(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C1)O[Si](C)(C)C)[Si](C)(C)C2653.3Standard polar33892256
Atenolol,1TBDMS,isomer #1CC(C)NCC(COC1=CC=C(CC(N)=O)C=C1)O[Si](C)(C)C(C)(C)C2650.6Semi standard non polar33892256
Atenolol,1TBDMS,isomer #2CC(C)NCC(O)COC1=CC=C(CC(=O)N[Si](C)(C)C(C)(C)C)C=C12668.9Semi standard non polar33892256
Atenolol,1TBDMS,isomer #3CC(C)N(CC(O)COC1=CC=C(CC(N)=O)C=C1)[Si](C)(C)C(C)(C)C2755.5Semi standard non polar33892256
Atenolol,2TBDMS,isomer #1CC(C)NCC(COC1=CC=C(CC(=O)N[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C2851.3Semi standard non polar33892256
Atenolol,2TBDMS,isomer #1CC(C)NCC(COC1=CC=C(CC(=O)N[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C2815.7Standard non polar33892256
Atenolol,2TBDMS,isomer #1CC(C)NCC(COC1=CC=C(CC(=O)N[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C3021.0Standard polar33892256
Atenolol,2TBDMS,isomer #2CC(C)N(CC(COC1=CC=C(CC(N)=O)C=C1)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3031.9Semi standard non polar33892256
Atenolol,2TBDMS,isomer #2CC(C)N(CC(COC1=CC=C(CC(N)=O)C=C1)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2808.1Standard non polar33892256
Atenolol,2TBDMS,isomer #2CC(C)N(CC(COC1=CC=C(CC(N)=O)C=C1)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3243.4Standard polar33892256
Atenolol,2TBDMS,isomer #3CC(C)N(CC(O)COC1=CC=C(CC(=O)N[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3030.5Semi standard non polar33892256
Atenolol,2TBDMS,isomer #3CC(C)N(CC(O)COC1=CC=C(CC(=O)N[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2919.1Standard non polar33892256
Atenolol,2TBDMS,isomer #3CC(C)N(CC(O)COC1=CC=C(CC(=O)N[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3113.2Standard polar33892256
Atenolol,2TBDMS,isomer #4CC(C)NCC(O)COC1=CC=C(CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C12988.3Semi standard non polar33892256
Atenolol,2TBDMS,isomer #4CC(C)NCC(O)COC1=CC=C(CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C12882.7Standard non polar33892256
Atenolol,2TBDMS,isomer #4CC(C)NCC(O)COC1=CC=C(CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C13063.7Standard polar33892256
Atenolol,3TBDMS,isomer #1CC(C)N(CC(COC1=CC=C(CC(=O)N[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3247.7Semi standard non polar33892256
Atenolol,3TBDMS,isomer #1CC(C)N(CC(COC1=CC=C(CC(=O)N[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3082.6Standard non polar33892256
Atenolol,3TBDMS,isomer #1CC(C)N(CC(COC1=CC=C(CC(=O)N[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3035.3Standard polar33892256
Atenolol,3TBDMS,isomer #2CC(C)NCC(COC1=CC=C(CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C3152.8Semi standard non polar33892256
Atenolol,3TBDMS,isomer #2CC(C)NCC(COC1=CC=C(CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C3080.1Standard non polar33892256
Atenolol,3TBDMS,isomer #2CC(C)NCC(COC1=CC=C(CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C2955.6Standard polar33892256
Atenolol,3TBDMS,isomer #3CC(C)N(CC(O)COC1=CC=C(CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3304.0Semi standard non polar33892256
Atenolol,3TBDMS,isomer #3CC(C)N(CC(O)COC1=CC=C(CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3177.8Standard non polar33892256
Atenolol,3TBDMS,isomer #3CC(C)N(CC(O)COC1=CC=C(CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3039.3Standard polar33892256
Atenolol,4TBDMS,isomer #1CC(C)N(CC(COC1=CC=C(CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3533.5Semi standard non polar33892256
Atenolol,4TBDMS,isomer #1CC(C)N(CC(COC1=CC=C(CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3333.9Standard non polar33892256
Atenolol,4TBDMS,isomer #1CC(C)N(CC(COC1=CC=C(CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2979.3Standard polar33892256
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified3.75 (0.037-7.5) uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>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
External LinksNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

Enzyme Details
1. Cytochrome P450 2D6
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
Enzyme Details
2. Beta-1 adrenergic receptor
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