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Compound Detail

CHEMBL13

METOPROLOL
💊 Approved Drug
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💊 Approved Drug
COCCc1ccc(OCC(O)CNC(C)C)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL13
Name METOPROLOL
Phase Approved
Structure Type MOL
InChI Key IUBSYMUCCVWXPE-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

(rs)-metoprolol Beatrolol CGP-2175 Dl-metoprolol H-93/26 Lopressidone Metoprolol Metoprolol slow release Seroken
11
Targets
37
Activities
3
Assay Types
30
PK Parameters
20
Publications
9
Known Names
20
Indications

Molecular Properties

267.4
MW (Da)
1.61
ALogP
4
HBA
2
HBD
50.7
PSA (Ų)
0.71
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1978
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 C15H25NO3
MW 267.37
Aromatic Rings 1
Heavy Atoms 19
NP-Likeness -0.38

Indications

Cardiovascular Diseases Atherosclerosis Atrial Fibrillation Breast Neoplasms Coronary Disease Diabetes Mellitus, Type 2 Heart Failure Heart Failure Hypercholesterolemia Hypertension Myocardial Infarction Myocardial Infarction Non-ST Elevated Myocardial Infarction Respiratory Distress Syndrome ST Elevation Myocardial Infarction Arrhythmias, Cardiac beta-Thalassemia Death, Sudden, Cardiac Heart Arrest Heart Diseases

ATC Classification

C07AB02
metoprolol
Level 1: CARDIOVASCULAR SYSTEM
Level 2: BETA BLOCKING AGENTS

Activity Summary

Ki 14 meas. best 7.35
Kd 13 meas. best 7.83
IC50 10 meas. best 6.75

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Beta-1 adrenergic receptor
CHEMBL5471
 Kd 7.83 7.4075 14.8 4
Beta-1 adrenergic receptor
CHEMBL213
 Kd 7.8 7.8 15.8 1
Beta-1 adrenergic receptor
CHEMBL3252
 Kd 7.64 7.64 22.9 3
Unchecked
CHEMBL612545
 Ki 7.35 7.35 45.0 1
Beta-1 adrenergic receptor
CHEMBL3440
 Ki 7.31 7.31 49.0 1
Beta-1 adrenergic receptor
CHEMBL213
 Ki 7.26 7.125 55.0 2
Beta-2 adrenergic receptor
CHEMBL210
 Kd 6.89 5.85 130.0 2
Beta-2 adrenergic receptor
CHEMBL5414
 Kd 6.79 6.79 162.2 3
Beta-1 adrenergic receptor
CHEMBL213
 IC50 6.75 6.75 176.0 1
Beta-1 adrenergic receptor
CHEMBL5471
 IC50 6.72 6.61 190.0 2
Beta-2 adrenergic receptor
CHEMBL210
 Ki 6.66 6.205 220.0 2
Beta-1 adrenergic receptor
CHEMBL3252
 Ki 6.4 5.82 398.1 5
Adrenergic receptor beta
CHEMBL2095166
 IC50 6.3 6.3 500.0 1
Beta-2 adrenergic receptor
CHEMBL210
 IC50 5.59 5.59 2573.0 1
Cytochrome P450 2J2
CHEMBL3491
 IC50 5.31 5.31 4870.0 1
5-hydroxytryptamine receptor 1A
CHEMBL273
 Ki 5.0 5.0 10000.0 1
Cytochrome P450 2D6
CHEMBL289
 IC50 4.62 4.62 24000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 12.15 mL.min-1.kg-1 Homo sapiens
CL 13.0 mL.min-1.kg-1 Homo sapiens
CL 12.4 mL.min-1.kg-1 Homo sapiens
CL 13.0 mL.min-1.kg-1 Homo sapiens
CL 185.0 mL.min-1.kg-1 Rattus norvegicus
CL 13.0 mL.min-1.kg-1 Homo sapiens
CL 15.0 mL.min-1.kg-1 Homo sapiens
CL 23.0 mL.min-1.kg-1 Canis lupus familiaris
CL 30.0 mL.min-1.kg-1 Macaca
CL 46.5 mL.min-1.kg-1 Homo sapiens
CL 13.0 uL.min-1.(10^6cells)-1 Homo sapiens
CL 8.41 uL.min-1.(10^6cells)-1 Homo sapiens
CL 13.3 mL.min-1.kg-1 Homo sapiens
CL 1.8 mL.min-1.g-1 Rattus norvegicus
CL 1.13 mL.min-1.g-1 Rattus norvegicus
CL 13.0 mL.min-1.kg-1 Homo sapiens
CL 33.0 mL.min-1.kg-1 Homo sapiens
F 49.0 % Homo sapiens
F 38.0 % Homo sapiens
F 95.0 % Homo sapiens
F 102.0 % Homo sapiens
Fu 0.89 - -
Fu 0.084 - -
Fu 0.89 - Homo sapiens
Fu 0.88 - Homo sapiens
Fu 0.88 - Homo sapiens
Fu 0.9 - Rattus norvegicus
Fu 1.0 - Homo sapiens
Fu 0.46 - Rattus norvegicus
Fu 0.8 - Not specified

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Beta-1 adrenergic receptor Kd = 14.79 nM 7.83 Compound was tested for its Beta-1 adrenergic receptor antagonistic activity on ... 6126588
Beta-1 adrenergic receptor Kd = 14.79 nM 7.83 In vitro beta-1 adrenergic receptor activity was determined via inhibition of th... 6134834
Beta-1 adrenergic receptor Kd = 14.79 nM 7.83 In vitro inhibitory activity against beta-1 adrenergic receptor measured by inhi... 2872332
Beta-1 adrenergic receptor Kd = 15.85 nM 7.8 Antagonist activity against beta-1 adrenergic receptor (unknown origin) 25799158
Beta-1 adrenergic receptor Kd = 22.91 nM 7.64 Antagonist activity was determined against beta-1 adrenergic receptor in spontan... 2884312
Beta-1 adrenergic receptor Kd = 22.91 nM 7.64 Cardioselectivity for the beta-1 adrenergic receptor was determined against isop... 2884312
Beta-1 adrenergic receptor Kd = 22.91 nM 7.64 Antagonist activity at rat beta1 adrenoceptor 27299736
Unchecked Ki = 45.0 nM 7.35 Displacement of [125I]dihydroalprenolol from beta adrenergic receptor 8496700
Beta-1 adrenergic receptor Ki = 49.0 nM 7.31 Displacement of [3H]CGP12177 from mouse beta1 adrenoceptor expressed in HEK293T ... 31151791
Beta-1 adrenergic receptor Ki = 55.0 nM 7.26 Displacement of [3H]CGP12177 from human beta1 adrenoceptor expressed in HEK293T ... 31151791
Beta-1 adrenergic receptor Ki = 102.0 nM 6.99 DRUGMATRIX: Adrenergic beta1 radioligand binding (ligand: [125I] Cyanopindolol) -
Beta-2 adrenergic receptor Kd = 130.0 nM 6.89 Displacement of [3H]DHA from inactive/G protein-uncoupled human beta2-AR express... 27239696
Beta-2 adrenergic receptor Kd = 162.18 nM 6.79 In vitro beta-2 adrenergic receptor activity was determined by measuring inhibit... 6134834
Beta-2 adrenergic receptor Kd = 162.18 nM 6.79 Beta-2 adrenergic receptor antagonistic activity on guinea pig tracheal chains 6126588
Beta-2 adrenergic receptor Kd = 162.18 nM 6.79 In vitro inhibitory activity against beta-2 adrenergic receptor was measured by ... 2872332
Beta-1 adrenergic receptor IC50 = 176.0 nM 6.75 DRUGMATRIX: Adrenergic beta1 radioligand binding (ligand: [125I] Cyanopindolol) -
Beta-1 adrenergic receptor IC50 = 190.0 nM 6.72 Tested for beta-1-adrenergic blocking effect by measuring the ability to inhibit... -
Beta-2 adrenergic receptor Ki = 220.0 nM 6.66 Displacement of [3H]CGP12177 from human beta2 adrenoceptor expressed in CHO cell... 31151791
Beta-1 adrenergic receptor IC50 = 320.0 nM 6.5 Tested for beta-2-adrenergic blocking effect by measuring the ability to inhibit... -
Beta-1 adrenergic receptor Ki = 398.11 nM 6.4 Antagonist activity at rat wild type beta-1 adrenergic receptor expressed in CHO... 16759089

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 746
- 10.5281/zenodo.13943903 ADMET 89
31158845 10.1038/s41586-019-1291-3 ADMET 62
- 10.6019/CHEMBL4295262 Unchecked 44
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
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
15920768 10.1002/jps.20373 ADMET 8
15658873 10.1021/jm049711o ADMET 5
33550184 10.1016/j.ejmech.2021.113232 ADMET 5
12061889 10.1021/jm0200409 ADMET 5
32480301 10.1016/j.ejmech.2020.112465 ADMET 5
17418579 10.1016/j.bmc.2007.03.040 ADMET 5
25799158 10.1021/acs.jmedchem.5b00201 Homo sapiens 5
16759089 10.1021/jm050624l Beta-1 adrenergic receptor 5
19397318 10.1021/jm9003945 No relevant target 5
18426954 10.1124/dmd.108.020479 ADMET 4

Data from ChEMBL 36 via Core Engine