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Compound Detail

CHEMBL24

ATENOLOL
💊 Approved Drug
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💊 Approved Drug
CC(C)NCC(O)COc1ccc(CC(N)=O)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL24
Name ATENOLOL
Phase Approved
Structure Type MOL
InChI Key METKIMKYRPQLGS-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Antipressan Atenamin Atenix-100 Atenix-25 Atenix-50 Atenolol Atenolol component of polycap Atenolol component of tenoretic Atenololum Betacard C07AB03 Corotenol +18 more
7
Targets
33
Activities
3
Assay Types
19
PK Parameters
20
Publications
30
Known Names
20
Indications
1
Mechanisms

Molecular Properties

266.3
MW (Da)
0.45
ALogP
4
HBA
3
HBD
84.6
PSA (Ų)
0.64
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1981
Availability Prescription
Chirality Racemic

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product
USAN Stem -olol
USAN Year 1976

Extended Properties

Molecular Formula C14H22N2O3
MW 266.34
Aromatic Rings 1
Heavy Atoms 19
NP-Likeness -0.62

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Beta-1 adrenergic receptor antagonist ANTAGONIST Beta-1 adrenergic receptor ✓ ✓

Indications

Angina Pectoris Cardiovascular Diseases Coronary Artery Disease Diabetes Mellitus Hypertension Myocardial Infarction Stroke Atrial Fibrillation Cerebrovascular Disorders Essential Hypertension Heart Diseases Heart Failure Hemangioma Hypertrophy, Left Ventricular Marfan Syndrome Mitral Valve Stenosis Myocardial Ischemia Vascular Diseases Stress Disorders, Post-Traumatic Orthostatic Intolerance

ATC Classification

C07AB03
atenolol
Level 1: CARDIOVASCULAR SYSTEM
Level 2: BETA BLOCKING AGENTS

Drug Warnings

Black Box Warning
cardiotoxicity
Country: United States

Activity Summary

IC50 13 meas. best 8.75
Ki 11 meas. best 6.82
Kd 9 meas. best 7.62

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Beta-1 adrenergic receptor
CHEMBL213
 IC50 8.75 6.5433 1.8 9
Beta-1 adrenergic receptor
CHEMBL5471
 Kd 7.62 7.35 24.0 4
Beta-1 adrenergic receptor
CHEMBL213
 Ki 6.82 6.45 150.0 6
Adrenergic receptor alpha-1
CHEMBL2094251
 IC50 6.64 6.64 230.0 1
Beta-2 adrenergic receptor
CHEMBL210
 Kd 6.58 6.25 260.0 2
Beta-2 adrenergic receptor
CHEMBL5414
 Kd 5.93 5.92 1174.9 3
Beta-2 adrenergic receptor
CHEMBL210
 Ki 5.02 5.01 9549.9 2
5-hydroxytryptamine receptor 1A
CHEMBL273
 Ki 5.0 5.0 10000.0 1
Beta-2 adrenergic receptor
CHEMBL210
 IC50 4.83 4.83 14634.0 1
Urease
CHEMBL4161
 IC50 4.19 4.19 64360.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 2.5 mL.min-1.kg-1 Homo sapiens
CL 2.5 mL.min-1.kg-1 Homo sapiens
CL 0.03 mL.min-1.kg-1 Homo sapiens
CL 2.5 mL.min-1.kg-1 Homo sapiens
CL 0.93 mL.min-1.g-1 Rattus norvegicus
CL 0.65 mL.min-1.g-1 Rattus norvegicus
F 79.0 % Homo sapiens
F 50.0 % Homo sapiens
F 54.0 % Homo sapiens
Fu 0.91 - Homo sapiens
Fu 0.94 - Homo sapiens
Fu 0.94 - Homo sapiens
Fu 1.0 - Rattus norvegicus
Fu 0.9 - Rattus norvegicus
Fu 1.0 - Rattus norvegicus
Fu 1.0 - Rattus norvegicus
MRT 6.3 hr Homo sapiens
T1/2 6.1 hr Homo sapiens
Vd 2.5 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Beta-1 adrenergic receptor IC50 = 1.77 nM 8.75 Percent inhibition against Beta-1 adrenergic receptor at 1 uM 16250647
Beta-1 adrenergic receptor Kd = 23.99 nM 7.62 In vitro inhibitory activity against beta-1 adrenergic receptor measured by inhi... 2872332
Beta-1 adrenergic receptor Kd = 23.99 nM 7.62 In vitro beta-1 adrenergic receptor activity was determined via inhibition of th... 6134834
Beta-1 adrenergic receptor Kd = 43.65 nM 7.36 Antagonist activity at beta1 adrenoceptor in guinea pig atrium assessed as inhib... 31474
Beta-1 adrenergic receptor Ki = 150.0 nM 6.82 Binding affinity to human adrenergic beta1 receptor by radioligand displacement ... 23466604
Beta-1 adrenergic receptor Ki = 160.0 nM 6.8 Binding affinity to Beta1 (unknown origin) assessed as inhibition constant 28849908
Beta-1 adrenergic receptor Kd = 158.49 nM 6.8 Activity at beta-1 adrenergic receptor 1361581
Beta-1 adrenergic receptor Ki = 170.0 nM 6.77 Displacement of [3H](-)-CGP12177 from human adrenergic beta1 receptor 21726069
Beta-1 adrenergic receptor IC50 = 210.0 nM 6.68 Displacement of [3H](-)CGP12177 from human recombinant Beta-1 adrenergic recepto... 26988801
Beta-1 adrenergic receptor IC50 = 210.0 nM 6.68 Displacement of [3H]CGP 12177 from human recombinant beta1 adrenergic receptor e... 27876250
Adrenergic receptor alpha-1 IC50 = 230.0 nM 6.64 Binding affinity to human adrenergic alpha1 receptor by radioligand displacement... 23582449
Beta-2 adrenergic receptor Kd = 260.0 nM 6.58 Displacement of [3H]DHA from inactive/G protein-uncoupled human beta2-AR express... 27239696
Beta-1 adrenergic receptor IC50 = 260.0 nM 6.58 Binding affinity to human adrenergic beta1 receptor by radioligand displacement ... 23466604
Beta-1 adrenergic receptor IC50 = 280.0 nM 6.55 Inhibition of Beta1 (unknown origin) 28849908
Beta-1 adrenergic receptor Ki = 430.0 nM 6.37 Displacement of radiolabeled atenolol from human adrenergic beta-1 receptor 18983139
Beta-1 adrenergic receptor IC50 = 600.0 nM 6.22 Displacement of radiolabeled atenolol from human adrenergic beta-1 receptor 18983139
Beta-1 adrenergic receptor Ki = 758.0 nM 6.12 DRUGMATRIX: Adrenergic beta1 radioligand binding (ligand: [125I] Cyanopindolol) -
Beta-2 adrenergic receptor Kd = 1174.9 nM 5.93 In vitro beta-2 adrenergic receptor activity was determined by measuring inhibit... 6134834
Beta-2 adrenergic receptor Kd = 1174.9 nM 5.93 In vitro inhibitory activity against beta-2 adrenergic receptor was measured by ... 2872332
Beta-2 adrenergic receptor Kd = 1200.0 nM 5.92 Displacement of [3H]DHA from inactive/G protein-uncoupled human beta2-AR express... 27239696

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 199
- 10.1101/2024.03.28.586928 ADMET 100
- 10.5281/zenodo.13943903 ADMET 89
31158845 10.1038/s41586-019-1291-3 ADMET 48
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
36796127 10.1016/j.bmc.2023.117203 No relevant target 12
21245286 10.1124/dmd.110.036806 Liver 12
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
20070106 10.1021/jm901371v Homo sapiens 8
9836611 10.1021/jm9810102 No relevant target 7
34096287 10.1021/acs.jmedchem.1c00211 ADMET 7
28993106 10.1016/j.bmc.2017.09.037 ADMET 6
32717478 10.1016/j.ejmech.2020.112492 ADMET 5
31699608 10.1016/j.bmcl.2019.126750 ADMET 5
15658873 10.1021/jm049711o ADMET 5
30099257 10.1016/j.ejmech.2018.07.053 ADMET 5
- 10.1016/S0960-894X(97)00046-2 ADMET 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4

Data from ChEMBL 36 via Core Engine