ATENOLOL

Search structure
Trade Names:
Synonyms:
Status: Approved (1981)
Entry Type: Small molecule
Molecule Category: Parent
ATC: C07AB03
UNII: 50VV3VW0TI

Structure
InChI Key METKIMKYRPQLGS-UHFFFAOYSA-N
Smile CC(C)NCC(O)COc1ccc(CC(N)=O)cc1
InChI
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)

Physicochemical Descriptors

Property Name Value
Molecular Formula C14H22N2O3
Molecular Weight 266.34
AlogP 0.45
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 8.0
Polar Surface Area 84.58
Molecular species BASE
Aromatic Rings 1.0
Heavy Atoms 19.0

Experimental and Estimated Properties

Property Name Value Unit Method
log P (octanol-water) 0.16 - EXP
Henry's Law Constant 1.37E-18 atm-m3/mole EST
Atmospheric OH Rate Constant 1.38E-10 cm3/molecule-sec EST
Melting Point 147 deg C EXP
Water Solubility 1.33E+04 mg/L EXP
Vapor Pressure 2.92E-10 mm Hg EST

Pharmacology

Action Mechanism of Action Reference
ANTAGONIST Beta-1 adrenergic receptor antagonist
Primary Target
β1-adrenoceptor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Auxiliary transport protein Fatty acid binding protein family
- - - 717000 -
Enzyme Hydrolase
- 375000 - 185000 -
Enzyme Transferase
- - - - 3.46-6.73
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- - - - -25.72-11.74
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Adrenergic receptor
- 1.77-1740 23.99-158.49 150-1513.56 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Serotonin receptor
- - - 10000 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 20.6-78.26
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - -

Metabolites

visNetwork

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Mitral Valve Stenosis 3 D008946 ClinicalTrials
Myocardial Ischemia 3 D017202 ClinicalTrials
Vascular Diseases 3 D014652 ClinicalTrials
Heart Diseases 3 D006331 ClinicalTrials
Hemangioma 3 D006391 ClinicalTrials
Atrial Fibrillation 3 D001281 ClinicalTrials
Heart Failure 3 D006333 ClinicalTrials
Cerebrovascular Disorders 3 D002561 ClinicalTrials
Hypertrophy, Left Ventricular 3 D017379 ClinicalTrials
Essential Hypertension 3 D000075222 ClinicalTrials
Marfan Syndrome 3 D008382 ClinicalTrials
Stress Disorders, Post-Traumatic 2 D013313 ClinicalTrials
Osteoporosis 1 D010024 ClinicalTrials
Orthostatic Intolerance 1 D054971 ClinicalTrials

Related Entries

MCS

Mixture

Side Effects from Label

Side effects Relative Frequency (%) Labels
Vascular disorders Hypotension 60.0
Cardiac disorders Cardiac failure 56.0
Cardiac disorders Ventricular tachycardia 52.0
Cardiac disorders Cardiac failure 46.0
Cardiac disorders Supraventricular tachycardia 45.0
Cardiac disorders Ventricular tachycardia 39.0
Vascular disorders Hypotension 34.0
Cardiac disorders Atrial fibrillation 29.0
Cardiac disorders Supraventricular tachycardia 28.0
General disorders and administration site conditions Asthenia 26.0
General disorders and administration site conditions Fatigue 26.0
Vascular disorders Hypotension 25.0
Vascular disorders Hypotension 24.6
Cardiac disorders Cardiac failure 24.0
Cardiac disorders Ventricular tachycardia 22.3
Cardiac disorders Ventricular tachycardia 22.0
Cardiac disorders Supraventricular tachycardia 19.3
Cardiac disorders Cardiac failure 19.0
Cardiac disorders Supraventricular tachycardia 19.0
Cardiac disorders Cardiac failure 18.9
Cardiac disorders Bradycardia 18.0
Cardiac disorders Bradycardia 17.6
Cardiac disorders Ventricular tachycardia 16.0
Vascular disorders Hypotension 15.0
Vascular disorders Hypotension 14.6
Cardiac disorders Bradycardia 14.5
Vascular disorders Hypotension 14.5
General disorders and administration site conditions Asthenia
Cardiac disorders Dizziness 13.0
General disorders and administration site conditions Fatigue
Cardiac disorders Atrial fibrillation 12.4
Cardiac disorders Atrial fibrillation 12.0
Psychiatric disorders Depression 12.0
General disorders and administration site conditions Peripheral coldness 12.0
Cardiac disorders Supraventricular tachycardia 11.5
Cardiac disorders Atrial fibrillation 11.0
Cardiac disorders Atrioventricular block 11.0
Cardiac disorders Bradycardia 10.3
Cardiac disorders Atrioventricular block 10.0
Psychiatric disorders Depression
Cardiac disorders Atrial flutter 7.0
General disorders and administration site conditions Asthenia 6.0
Cardiac disorders Dizziness
Cardiac disorders Dyspnoea 6.0
General disorders and administration site conditions Fatigue 6.0
Cardiac disorders Myocardial infarction 6.0
General disorders and administration site conditions Asthenia
Cardiac disorders Atrial fibrillation 5.0
General disorders and administration site conditions Fatigue
Nervous system disorders Orthostatic hypotension
General disorders and administration site conditions Peripheral coldness
Cardiac disorders Atrial fibrillation 4.92
Cardiac disorders Atrioventricular block 4.51
Cardiac disorders Atrioventricular block 4.5
Cardiac disorders Atrioventricular block 4.3
Cardiac disorders Atrioventricular block 4.29
Cardiac disorders Atrial flutter 4.0
Cardiac disorders Cardiogenic shock 4.0
Cardiac disorders Dizziness 4.0
Cardiac disorders Dyspnoea
Gastrointestinal disorders Nausea 4.0
Nervous system disorders Orthostatic hypotension 4.0
General disorders and administration site conditions Asthenia 3.0
Cardiac disorders Atrial flutter 3.0
Cardiac disorders Bradycardia 3.0
Immune system disorders Bronchospasm 3.0
Gastrointestinal disorders Diarrhoea 3.0
Cardiac disorders Dizziness 3.0
General disorders and administration site conditions Fatigue 3.0
General disorders and administration site conditions Lethargy 3.0
Gastrointestinal disorders Nausea 3.0
Musculoskeletal and connective tissue disorders Pain in extremity 3.0
Cardiac disorders Cardiac failure 2.9
Cardiac disorders Myocardial infarction 2.6
Cardiac disorders Myocardial infarction 2.58
Immune system disorders Bronchospasm 2.0
Cardiac disorders Cardiac septal defect 2.0
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Diarrhoea 2.0
Cardiac disorders Mitral valve incompetence 2.0
Nervous system disorders Orthostatic hypotension 2.0
Gastrointestinal disorders Regurgitation 2.0
Nervous system disorders Somnolence 2.0
Cardiac disorders Ventricular septal defect 2.0
Ear and labyrinth disorders Vertigo 2.0
Cardiac disorders Cardiogenic shock 1.72
Cardiac disorders Atrioventricular block 1.7
Cardiac disorders Cardiogenic shock 1.7
Cardiac disorders Atrial flutter 1.64
Cardiac disorders Atrial flutter 1.6
Cardiac disorders Bradycardia 1.3
Vascular disorders Hypotension 1.3
Immune system disorders Bronchospasm 1.23
Immune system disorders Bronchospasm 1.2
General disorders and administration site conditions Asthenia
Cardiac disorders Cardiogenic shock 1.0
Cardiac disorders Dizziness
Cardiac disorders Dizziness 1.0
Cardiac disorders Dyspnoea
General disorders and administration site conditions Fatigue
General disorders and administration site conditions Lethargy 1.0
Gastrointestinal disorders Nausea
Nervous system disorders Orthostatic hypotension
Musculoskeletal and connective tissue disorders Pain in extremity
Renal and urinary disorders Renal failure 1.0
Immune system disorders Bronchospasm 0.9
Cardiac disorders Cardiac septal defect 0.9
Cardiac disorders Mitral valve incompetence 0.9
Gastrointestinal disorders Regurgitation 0.9
Cardiac disorders Ventricular septal defect 0.9
Immune system disorders Bronchospasm 0.858
Cardiac disorders Cardiac septal defect 0.858
Cardiac disorders Mitral valve incompetence 0.858
Gastrointestinal disorders Regurgitation 0.858
Cardiac disorders Ventricular septal defect 0.858
Cardiac disorders Dizziness
General disorders and administration site conditions Lethargy
Immune system disorders Bronchospasm 0.62
General disorders and administration site conditions Asthenia 0.6
Psychiatric disorders Depression 0.6
Cardiac disorders Dyspnoea 0.6
General disorders and administration site conditions Fatigue 0.6
Nervous system disorders Somnolence 0.6
General disorders and administration site conditions Asthenia
Psychiatric disorders Depression
General disorders and administration site conditions Fatigue
Musculoskeletal and connective tissue disorders Pain in extremity
General disorders and administration site conditions Peripheral coldness
Nervous system disorders Somnolence
Ear and labyrinth disorders Vertigo
Cardiac disorders Cardiogenic shock 0.44
Cardiac disorders Cardiogenic shock 0.41
Renal and urinary disorders Renal failure 0.41
Cardiac disorders Cardiogenic shock 0.4
Renal and urinary disorders Renal failure 0.4
Cardiac disorders Cardiac arrest 0.34
Cardiac disorders Arrhythmia 0.27
Ear and labyrinth disorders Vertigo
Cardiac disorders Atrioventricular block 0.06
Cardiac disorders Cardiac arrest 0.06
Cardiac disorders Arrhythmia 0.04
Cardiac disorders Cardiogenic shock 0.04
Immune system disorders Bronchospasm 0.01
Cardiac disorders Cardiac failure 0.01

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
12.26
Nervous system disorders
11.62
Cardiac disorders
11.12
Vascular disorders
9.43
Psychiatric disorders
7.19
Injury, poisoning and procedural complications
6.74
Gastrointestinal disorders
6.52
Investigations
6.32
Respiratory, thoracic and mediastinal disorders
5.55
Skin and subcutaneous tissue disorders
3.89
Musculoskeletal and connective tissue disorders
3.56
Metabolism and nutrition disorders
3.23
Immune system disorders
2.26

Cross References

Resources Reference
CAS NUMBER 29122-68-7
ChEBI 2904
ChEMBL CHEMBL24
DrugBank DB00335
DrugCentral 255
EPA CompTox DTXSID2022628
FDA SRS 50VV3VW0TI
Human Metabolome Database HMDB01924
Guide to Pharmacology 548
PharmGKB PA448499
PubChem 2249
SureChEMBL SCHEMBL4362
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