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Compound Detail

CHEMBL813

EPROSARTAN
💊 Approved Drug
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💊 Approved Drug
CCCCc1ncc(/C=C(\Cc2cccs2)C(=O)O)n1Cc1ccc(C(=O)O)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL813
Name EPROSARTAN
Phase Approved
Structure Type MOL
InChI Key OROAFUQRIXKEMV-LDADJPATSA-N
Therapeutic ✓ Yes

Known Names

Eprosartan SK&F 108566 SK&F-108566 SK-108566 Teveten
8
Targets
14
Activities
1
Assay Types
13
PK Parameters
20
Publications
5
Known Names
5
Indications

Molecular Properties

424.5
MW (Da)
4.74
ALogP
5
HBA
2
HBD
92.4
PSA (Ų)
0.46
QED
0
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1997
Availability Discontinued
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -sartan
USAN Year 1994

Extended Properties

Molecular Formula C23H24N2O4S
MW 424.52
Aromatic Rings 3
Heavy Atoms 30
NP-Likeness -0.86

Indications

Cardiovascular Diseases Essential Hypertension Severe Acute Respiratory Syndrome Severe Acute Respiratory Syndrome Kidney Diseases

ATC Classification

C09CA02
eprosartan
Level 1: CARDIOVASCULAR SYSTEM
Level 2: AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM

Activity Summary

IC50 14 meas. best 9.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Angiotensin II receptor
CHEMBL2094112
 IC50 9.0 7.72 1.0 2
Angiotensin II receptor (AT-1) type-1
CHEMBL2094250
 IC50 9.0 8.62 1.0 3
Type-2 angiotensin II receptor
CHEMBL257
 IC50 9.0 9.0 1.0 1
Type-1 angiotensin II receptor B
CHEMBL263
 IC50 9.0 9.0 1.0 1
Unchecked
CHEMBL612545
 IC50 8.82 7.0967 1.5 3
Type-1 angiotensin II receptor
CHEMBL227
 IC50 8.7 8.42 2.0 2
ATP-binding cassette sub-family C member 3
CHEMBL5918
 IC50 5.18 5.18 6650.0 1
ATP-binding cassette sub-family C member 2
CHEMBL5748
 IC50 4.24 4.24 57900.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 1.9 mL.min-1.kg-1 Homo sapiens
CL 1.2 mL.min-1.kg-1 Homo sapiens
CL 1.9 mL.min-1.kg-1 Homo sapiens
CL 1.9 mL.min-1.kg-1 Homo sapiens
F 13.0 % Homo sapiens
Fu 0.017 - Homo sapiens
Fu 0.017 - Homo sapiens
MRT 1.5 hr Homo sapiens
T1/2 1.417 hr Rattus norvegicus
T1/2 5.0 hr -
T1/2 7.0 hr Homo sapiens
T1/2 2.1 hr Homo sapiens
Vd 0.16 L.kg-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Type-1 angiotensin II receptor B IC50 = 1.0 nM 9.0 Tested for inhibition of [125I]- AII specific binding to rat mesenteric arteries... -
Type-2 angiotensin II receptor IC50 = 1.0 nM 9.0 In vitro inhibition of [125I]AII specific binding towards Angiotensin II recepto... 2016730
Angiotensin II receptor (AT-1) type-1 IC50 = 1.0 nM 9.0 Compound was tested for inhibition of 125 I-Angiotensin II specific binding to r... -
Angiotensin II receptor IC50 = 1.0 nM 9.0 Inhibition of [125I]AII binding to Angiotensin II receptor, type 1 of rat mesent... 8515425
Angiotensin II receptor (AT-1) type-1 IC50 = 1.5 nM 8.82 Antagonistic activity against [125I]AngII binding to Angiotensin II receptor, ty... 8576904
Unchecked IC50 = 1.5 nM 8.82 Antagonist activity at angiotensin AT1 receptor in rat mesenteric artery membran... 21071232
Type-1 angiotensin II receptor IC50 = 2.0 nM 8.7 Tested for Angiotensin II receptor, type 1 affinity in the absence of bovine ser... -
Type-1 angiotensin II receptor IC50 = 7.3 nM 8.14 Tested for Angiotensin II receptor, type 1 affinity in the presence of 0.25% bov... -
Angiotensin II receptor (AT-1) type-1 IC50 = 9.2 nM 8.04 Antagonistic activity against [125I]AngII binding to Angiotensin II receptor, ty... 8576904
Unchecked IC50 = 9.2 nM 8.04 Antagonist activity at angiotensin AT1 receptor in rat adrenal cortical membrane... 21071232
Angiotensin II receptor IC50 = 363.0 nM 6.44 Inhibition of [125I]AII binding to Angiotensin II receptor, type 1 of rat mesent... 8515425
ATP-binding cassette sub-family C member 3 IC50 = 6650.0 nM 5.18 Inhibition of human MRP3 overexpressed in Sf9 insect cell membrane vesicles asse... 23956101
Unchecked IC50 = 36850.0 nM 4.43 Inhibition of HIV1 integrase/LEDGF-75 (unknown origin) interaction 24025027
ATP-binding cassette sub-family C member 2 IC50 = 57900.0 nM 4.24 Inhibition of human MRP2 overexpressed in Sf9 cell membrane vesicles assessed as... 23956101

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
20070106 10.1021/jm901371v Homo sapiens 8
8515425 10.1021/jm00065a011 Angiotensin II receptor 5
- 10.1016/S0960-894X(01)81116-1 Rattus norvegicus 4
18426954 10.1124/dmd.108.020479 ADMET 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
15974591 10.1021/jm049024x ADMET 4
12773029 10.1021/jm0204237 ADMET 4
37468498 10.1038/s41467-023-40064-9 Type-1 angiotensin II receptor 4
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 4
37468498 10.1038/s41467-023-40064-9 Histamine H1 receptor 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 3
15974591 10.1021/jm049024x Type-1 angiotensin II receptor 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 3
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 3
8576904 10.1021/jm9504722 Angiotensin II receptor (AT-1) type-1 2
8576904 10.1021/jm9504722 Rattus norvegicus 2
37468498 10.1038/s41467-023-40064-9 Histamine H2 receptor 2

Data from ChEMBL 36 via Core Engine