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Compound Detail

CHEMBL1095097

EPLERENONE
💊 Approved Drug
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💊 Approved Drug
COC(=O)[C@@H]1CC2=CC(=O)CC[C@]2(C)[C@@]23O[C@@H]2C[C@@]2(C)[C@@H](CC[C@@]24CCC(=O)O4)[C@H]13

Basic Information

ChEMBL ID CHEMBL1095097
Name EPLERENONE
Phase Approved
Structure Type MOL
InChI Key JUKPWJGBANNWMW-VWBFHTRKSA-N
Therapeutic ✓ Yes

Known Names

Eplerenona Eplerenone Inspra SC-66110 SC-6611O
6
Targets
27
Activities
3
Assay Types
6
PK Parameters
20
Publications
5
Known Names
16
Indications
1
Mechanisms

Molecular Properties

414.5
MW (Da)
3.12
ALogP
6
HBA
0
HBD
82.2
PSA (Ų)
0.48
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2002
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -renone
USAN Year 1997

Extended Properties

Molecular Formula C24H30O6
MW 414.50
Aromatic Rings 0
Heavy Atoms 30
NP-Likeness 2.30

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Mineralocorticoid receptor antagonist ANTAGONIST Mineralocorticoid receptor

Indications

Cardiovascular Diseases Heart Failure Heart Failure Hypertension Myocardial Infarction Stroke Cardiomyopathies Essential Hypertension Muscular Dystrophy, Duchenne Renal Insufficiency, Chronic Atrial Fibrillation Breast Neoplasms Central Serous Chorioretinopathy Diabetic Nephropathies Hyperparathyroidism, Primary Diabetes Mellitus, Type 2

ATC Classification

C03DA04
eplerenone
Level 1: CARDIOVASCULAR SYSTEM
Level 2: DIURETICS

Activity Summary

IC50 22 meas. best 7.4
Ki 4 meas. best 7.35
EC50 1 meas. best 7.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mineralocorticoid receptor
CHEMBL3507
IC50 7.4 7.4 39.8 1
Mineralocorticoid receptor
CHEMBL3507
Ki 7.35 7.35 44.4 1
Mineralocorticoid receptor
CHEMBL1994
IC50 7.2 6.4675 63.1 16
Mineralocorticoid receptor
CHEMBL1994
EC50 7.0 7.0 100.0 1
Unchecked
CHEMBL612545
IC50 7.0 5.57 101.0 2
Mineralocorticoid receptor
CHEMBL1994
Ki 6.9 6.9 125.9 1
Glucocorticoid receptor
CHEMBL2034
Ki 5.5 5.5 3162.3 1
Androgen receptor
CHEMBL1871
IC50 4.77 4.77 17000.0 1
Glucocorticoid receptor
CHEMBL2034
IC50 4.75 4.51 18000.0 2
Progesterone receptor
CHEMBL208
Ki 4.7 4.7 19952.6 1

Pharmacokinetic Data

Parameter Value Units Species
CL 7.9 mL.min-1.g-1 Homo sapiens
CL 9.0 mL.min-1.g-1 Homo sapiens
CL 17.0 mL.min-1.kg-1 Rattus norvegicus
F 16.0 % Rattus norvegicus
Fu 0.76 - Rattus norvegicus
T1/2 1.3 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mineralocorticoid receptor IC50 = 39.81 nM 7.4 Antagonist activity at gal4-fused rat mineralocorticoid receptor LBD in expresse... 30596500
Mineralocorticoid receptor Ki = 44.4 nM 7.35 Displacement of [3H]-aldosterone from rat mineralocorticoid receptor incubated o... 35652647
Mineralocorticoid receptor IC50 = 63.1 nM 7.2 Modulation activity at human mineralocorticoid receptor in human EA.hy926 cells ... 30596500
Unchecked IC50 = 101.0 nM 7.0 Antagonist activity at human mineralocorticoid receptor S810L mutant expressed i... 35652647
Mineralocorticoid receptor EC50 = 100.0 nM 7.0 Modulation activity at human mineralocorticoid receptor in human EA.hy926 cells ... 30596500
Mineralocorticoid receptor IC50 = 122.0 nM 6.91 Antagonist activity at mineralocorticoid receptor LBD expressed in human HUH7 ce... 20672820
Mineralocorticoid receptor IC50 = 122.0 nM 6.91 Antagonist activity at Gal4-tagged mineralocorticoid receptor expressed in human... 20672822
Mineralocorticoid receptor IC50 = 122.0 nM 6.91 Antagonist activity at mineralocorticoid receptor (unknown origin) by Gal4-based... 24738581
Mineralocorticoid receptor Ki = 125.89 nM 6.9 Displacement of [3H]-aldosterone to human mineralocorticoid receptor LBD by radi... 30596500
Mineralocorticoid receptor IC50 = 135.0 nM 6.87 Antagonist activity at Gal4-fused mineralocorticoid receptor expressed in human ... 20408553
Mineralocorticoid receptor IC50 = 178.0 nM 6.75 Antagonist activity at human wild-type mineralocorticoid receptor expressed in C... 35652647
Mineralocorticoid receptor IC50 = 226.0 nM 6.65 Displacement of [3H]-aldosterone from recombinant human mineralocorticoid recept... 35652647
Mineralocorticoid receptor IC50 = 240.0 nM 6.62 Antagonist activity at human mineralocorticoid receptor assessed as inhibition o... 23777778
Mineralocorticoid receptor IC50 = 244.0 nM 6.61 Antagonist activity at mineralocorticoid receptor (unknown origin) by PathHunter... 24630411
Mineralocorticoid receptor IC50 = 244.0 nM 6.61 Antagonist activity at human full-length MCR assessed as inhibition of receptor ... 27161805
Mineralocorticoid receptor IC50 = 398.11 nM 6.4 Antagonist activity at full length human mineralocorticoid receptor expressed in... 30596500
Mineralocorticoid receptor IC50 = 794.33 nM 6.1 Antagonist activity at gal4-fused human mineralocorticoid receptor LBD expressed... 30596500
Mineralocorticoid receptor IC50 = 1300.0 nM 5.89 Antagonist activity at human mineralocorticoid receptor expressed in COS1 cells ... 25187277
Mineralocorticoid receptor IC50 = 1300.0 nM 5.89 Antagonist activity at human MR transfected in human COS1 cells after 1 day by l... 22074142
Mineralocorticoid receptor IC50 = 2600.0 nM 5.58 Displacement of [3H]aldosterone from cytosolic human MR expressed in HEK293 cell... 22074142

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
30596500 10.1021/acs.jmedchem.8b01523 Mineralocorticoid receptor 11
35652647 10.1021/acs.jmedchem.2c00402 Rattus norvegicus 10
30596500 10.1021/acs.jmedchem.8b01523 ADMET 7
35652647 10.1021/acs.jmedchem.2c00402 Unchecked 5
24422519 10.1021/jm401430e Homo sapiens 4
30596500 10.1021/acs.jmedchem.8b01523 Rattus norvegicus 4
20672822 10.1021/jm100505n Unchecked 4
35652647 10.1021/acs.jmedchem.2c00402 Mineralocorticoid receptor 4
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 3
37468498 10.1038/s41467-023-40064-9 Histamine H1 receptor 3
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 Estrogen receptor 3
37468498 10.1038/s41467-023-40064-9 Glucocorticoid receptor 3
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 3
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 3
26403853 10.1021/acs.jmedchem.5b00851 Rattus norvegicus 3
25187277 10.1016/j.bmc.2014.07.038 Mineralocorticoid receptor 3
31749913 10.1021/acsmedchemlett.9b00430 ADMET 3
20672820 10.1021/jm100506y Rattus norvegicus 3

Data from ChEMBL 36 via Core Engine