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Compound Detail

CHEMBL1513

IRBESARTAN
💊 Approved Drug
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💊 Approved Drug
CCCCC1=NC2(CCCC2)C(=O)N1Cc1ccc(-c2ccccc2-c2nnn[nH]2)cc1

Basic Information

ChEMBL ID CHEMBL1513
Name IRBESARTAN
Phase Approved
Structure Type MOL
InChI Key YOSHYTLCDANDAN-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Aprovel Avapro BMS-186295 Ifirmasta Irbesartan Irbesartan bms Irbesartan component of avalide Irbesartan component of coaprovel Irbesartan component of ibersartan/hydrochlorothiazide ibersartan Irbesartan component of ibersartan/hydrochlorothiazide teva ibersartan Irbesartan component of ibersartan/hydrochlorothiazide zentiva ibersartan Irbesartan component of ifirmacombi +9 more
17
Targets
40
Activities
3
Assay Types
28
PK Parameters
20
Publications
21
Known Names
20
Indications
1
Mechanisms

Molecular Properties

428.5
MW (Da)
4.78
ALogP
5
HBA
1
HBD
87.1
PSA (Ų)
0.59
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1997
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -sartan
USAN Year 1996

Extended Properties

Molecular Formula C25H28N6O
MW 428.54
Aromatic Rings 3
Heavy Atoms 32
NP-Likeness -0.74

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Type-1 angiotensin II receptor antagonist ANTAGONIST Type-1 angiotensin II receptor

Indications

Cardiovascular Diseases Diabetes Mellitus, Type 2 Diabetic Nephropathies Hypertension Kidney Failure, Chronic Kidney Failure, Chronic Acute Kidney Injury Atrial Fibrillation Ehlers-Danlos Syndrome Essential Hypertension Glomerulonephritis, IGA Glomerulosclerosis, Focal Segmental Heart Failure Hepatitis C, Chronic Hypercholesterolemia Myocardial Ischemia Renal Insufficiency, Chronic Sepsis Severe Acute Respiratory Syndrome Severe Acute Respiratory Syndrome

ATC Classification

C09CA04
irbesartan
Level 1: CARDIOVASCULAR SYSTEM
Level 2: AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM

Drug Warnings

Black Box Warning
teratogenicity
Country: United States
Black Box Warning
cardiotoxicity
Country: United States

Activity Summary

IC50 27 meas. best 9.24
Ki 11 meas. best 9.39
EC50 2 meas. best 6.39

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
Ki 9.39 8.9767 0.4 3
Unchecked
CHEMBL612545
IC50 9.24 8.776 0.6 5
Type-1 angiotensin II receptor B
CHEMBL263
Ki 9.1 9.1 0.8 1
Type-1 angiotensin II receptor
CHEMBL227
Ki 9.1 8.912 0.8 5
Type-1 angiotensin II receptor A
CHEMBL329
IC50 9.05 9.05 0.9 1
Angiotensin II receptor
CHEMBL2094112
IC50 8.89 8.89 1.3 1
Type-1 angiotensin II receptor B
CHEMBL263
IC50 8.89 8.89 1.3 2
Angiotensin II receptor (AT-1) type-1
CHEMBL2094250
IC50 8.89 8.89 1.3 2
Type-1 angiotensin II receptor
CHEMBL227
IC50 8.52 8.14 3.0 3
Angiotensin II receptor
CHEMBL2094256
IC50 8.52 8.52 3.0 1
Oryctolagus cuniculus
CHEMBL374
IC50 8.4 8.4 4.0 3
HASMC
CHEMBL614150
IC50 6.5 6.5 320.0 1
Leukotriene B4 receptor 2
CHEMBL3191
EC50 6.39 6.39 410.0 1
Hepatitis B virus
CHEMBL613497
IC50 5.48 5.48 3300.0 1
Bile salt export pump
CHEMBL6020
IC50 5.14 5.14 7300.0 3
Hepatitis delta virus
CHEMBL4888466
EC50 5.03 5.03 9400.0 1
Endothelin-1 receptor
CHEMBL252
Ki 5.0 5.0 10000.0 1
Hepatic sodium/bile acid cotransporter
CHEMBL5287
Ki 4.92 4.92 11900.0 1
ATP-binding cassette sub-family C member 3
CHEMBL5918
IC50 4.68 4.68 21100.0 1
Hepatic sodium/bile acid cotransporter
CHEMBL5287
IC50 4.52 4.52 30000.0 1
ATP-binding cassette sub-family C member 4
CHEMBL1743128
IC50 4.08 4.08 83200.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 22656.91 ng.hr.mL-1 Homo sapiens
CL 3.85 mL.min-1.kg-1 Homo sapiens
CL 2.3 mL.min-1.kg-1 Homo sapiens
CL 9.01 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 10.47 uL.min-1.(10^6cells)-1 Homo sapiens
CL 17.78 mL.min-1.g-1 Homo sapiens
CL 2.12 mL.min-1.kg-1 Homo sapiens
CL 39.0 mL.min-1.kg-1 Homo sapiens
CL 12.1 mL.min-1.kg-1 Macaca fascicularis
CL 2.1 mL.min-1.kg-1 Homo sapiens
Cmax 3033.56 nM Homo sapiens
Cmax 3505.0 nM Homo sapiens
Excretion 2.2 % Homo sapiens
F 90.0 % Homo sapiens
F 70.0 % Homo sapiens
F 70.0 % Homo sapiens
F 60.0 % Homo sapiens
Fu 0.1 - Homo sapiens
Fu 0.000126 - Macaca fascicularis
Fu 0.000155 - Homo sapiens
MRT 6.8 hr Homo sapiens
T1/2 10.0 hr -
T1/2 21.0 hr Homo sapiens
T1/2 14.0 hr Homo sapiens
T1/2 13.0 hr Homo sapiens
Tmax 1.2 hr Homo sapiens
Vd 0.9 L.kg-1 Homo sapiens
Vd 2.9 L.kg-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 0.41 nM 9.39 Displacement of [I125]angiotensin2 from AT1 receptor in Sprague-Dawley rat VSMC ... 22410249
Unchecked IC50 = 0.58 nM 9.24 Displacement of [I125]angiotensin2 from AT1 receptor in Sprague-Dawley rat VSMC ... 22410249
Type-1 angiotensin II receptor B Ki = 0.8 nM 9.1 Compound was evaluated for its binding affinity towards rat Angiotensin II recep... 12190306
Type-1 angiotensin II receptor Ki = 0.8 nM 9.1 Inhibitory concentration against angiotensin II receptor, type 1 16220969
Type-1 angiotensin II receptor Ki = 0.8 nM 9.1 Binding affinity to AT1 receptor 22931505
Type-1 angiotensin II receptor A IC50 = 0.9 nM 9.05 Displacement of [125I]- Ang II from type 1 Angiotensin II receptor -
Unchecked Ki = 1.05 nM 8.98 Displacement of 125I-Ang2 from AT1 receptor in SPF Sprague-Dawley rat vascular s... 27474928
Type-1 angiotensin II receptor Ki = 1.1 nM 8.96 Compound was evaluated for its binding affinity towards human Angiotensin II rec... 12190306
Angiotensin II receptor IC50 = 1.3 nM 8.89 Inhibition of [125I]-AII binding to Angiotensin II receptor of rat uterine membr... -
Unchecked IC50 = 1.3 nM 8.89 Binding affinity to angiotensin AT1 receptor in rat liver membranes 21071232
Angiotensin II receptor (AT-1) type-1 IC50 = 1.3 nM 8.89 Inhibitory activity against Angiotensin II receptor, type 1 in rat liver membran... 8576904
Type-1 angiotensin II receptor B IC50 = 1.3 nM 8.89 In vitro inhibition of specific binding of [125I]AII to Angiotensin II receptor,... -
Angiotensin II receptor (AT-1) type-1 IC50 = 1.3 nM 8.89 Binding affinity towards Angiotensin II receptor, type 1 in rat liver membrane u... -
Type-1 angiotensin II receptor B IC50 = 1.3 nM 8.89 Binding affinity for Angiotensin II receptor, type 1 measured by ability to disp... 8230127
Unchecked IC50 = 1.46 nM 8.84 Displacement of 125I-Ang2 from AT1 receptor in SPF Sprague-Dawley rat vascular s... 27474928
Type-1 angiotensin II receptor Ki = 2.0 nM 8.7 Binding affinity against AT1 in human hepatoma cell line, PLC-PRF-5 10893306
Type-1 angiotensin II receptor Ki = 2.0 nM 8.7 In vitro binding affinity towards Angiotensin II receptor, type 1 of human hepat... 12361407
Unchecked Ki = 2.75 nM 8.56 Displacement of [125I]Angiotensin-2 from angiotensin AT1 receptor in Sprague-Daw... 23122933
Type-1 angiotensin II receptor IC50 = 2.999 nM 8.52 GPCR PRESTO-Tango dose-response in antagonist mode with target: AGTR1 -
Angiotensin II receptor IC50 = 3.0 nM 8.52 In vitro antagonist activity, Inhibition of angiotensin II (50 nM) mediated incr... 10893306

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5724801 Fibroblast 304
- 10.6019/CHEMBL5058577 HEK-293T 304
- 10.6019/CHEMBL5058577 Fibroblast 304
- 10.6019/CHEMBL5724801 U2OS 304
- 10.6019/CHEMBL5058577 U2OS 304
- 10.6019/CHEMBL5724801 HEK-293T 304
- 10.6019/CHEMBL3885881 Rattus norvegicus 192
- 10.5281/zenodo.13943903 ADMET 89
31158845 10.1038/s41586-019-1291-3 ADMET 71
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
28666735 10.1016/j.bmcl.2017.06.051 Type-1 angiotensin II receptor 12
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
- 10.6019/CHEMBL5058564 U2OS 8
22410249 10.1016/j.bmc.2012.02.003 Rattus norvegicus 8
- 10.6019/CHEMBL5058564 Fibroblast 8
32985885 10.1021/acs.jmedchem.0c01033 ADMET 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
- 10.1016/S0960-894X(01)81139-2 Rattus norvegicus 7
- 10.1016/S0960-894X(01)81139-2 Monkey 6
- 10.6019/CHEMBL5209801 CX3C chemokine receptor 1 5

Data from ChEMBL 36 via Core Engine