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Compound Detail

CHEMBL1017

TELMISARTAN
💊 Approved Drug
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💊 Approved Drug
CCCc1nc2c(C)cc(-c3nc4ccccc4n3C)cc2n1Cc1ccc(-c2ccccc2C(=O)O)cc1

Basic Information

ChEMBL ID CHEMBL1017
Name TELMISARTAN
Phase Approved
Structure Type MOL
InChI Key RMMXLENWKUUMAY-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

BIBR 277 SE BIBR-277 BIBR-277 SE BIBR-277-SE Bibr-277se C09CA07 Kinzalmono Kinzalmono (previously telmisartan boehringer ingelheim pharma kg) Micardis Pritor Semintra Telmisartan +11 more
22
Targets
60
Activities
4
Assay Types
30
PK Parameters
20
Publications
23
Known Names
20
Indications
1
Mechanisms

Molecular Properties

514.6
MW (Da)
7.26
ALogP
5
HBA
1
HBD
72.9
PSA (Ų)
0.24
QED
2
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1998
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -sartan
USAN Year 1997

Extended Properties

Molecular Formula C33H30N4O2
MW 514.63
Aromatic Rings 6
Heavy Atoms 39
NP-Likeness -0.99

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 Hypertension Myocardial Infarction Stroke Albuminuria Diabetes Mellitus, Type 2 Diabetic Nephropathies Essential Hypertension Heart Diseases Kidney Diseases Kidney Failure, Chronic Lipid Metabolism Disorders Polycystic Kidney Diseases Severe Acute Respiratory Syndrome Severe Acute Respiratory Syndrome Alzheimer Disease HIV Infections HIV Infections Neuralgia

ATC Classification

C09CA07
telmisartan
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 33 meas. best 9.48
EC50 16 meas. best 6.16
Ki 10 meas. best 9.64
Kd 1 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Type-1 angiotensin II receptor A
CHEMBL329
Ki 9.64 9.64 0.2 2
Type-2 angiotensin II receptor
CHEMBL4607
IC50 9.48 9.48 0.3 1
Type-1 angiotensin II receptor
CHEMBL227
IC50 9.31 8.663 0.5 10
Unchecked
CHEMBL612545
Ki 8.56 8.495 2.8 2
Type-1 angiotensin II receptor B
CHEMBL263
IC50 8.52 8.52 3.0 1
Unchecked
CHEMBL612545
IC50 8.42 5.8067 3.8 3
Plasmodium berghei
CHEMBL612653
IC50 7.6 7.6 25.0 1
Plasmodium
CHEMBL4888483
IC50 7.6 7.6 25.0 1
Liver
CHEMBL613642
IC50 7.15 7.15 70.5 1
Cytochrome P450 2J2
CHEMBL3491
Ki 7.0 6.86 100.0 2
Cytochrome P450 2J2
CHEMBL3491
IC50 6.38 6.3067 420.0 3
Peroxisome proliferator-activated receptor gamma
CHEMBL235
EC50 6.16 5.5708 700.0 13
Solute carrier organic anion transporter family member 1B3
CHEMBL1743121
Ki 6.02 6.02 960.0 1
Solute carrier organic anion transporter family member 1B1
CHEMBL1697668
Ki 5.99 5.99 1030.0 1
Peroxisome proliferator-activated receptor gamma
CHEMBL235
Ki 5.97 5.97 1080.0 1
Solute carrier organic anion transporter family member 1B3
CHEMBL1743121
IC50 5.9 5.9 1258.9 1
Plasmodium falciparum
CHEMBL364
IC50 5.79 5.79 1612.0 1
Solute carrier organic anion transporter family member 1B1
CHEMBL1697668
IC50 5.73 5.73 1862.1 1
Glycine receptor subunit alpha-1
CHEMBL5845
EC50 5.5 5.5 3200.0 1
Peroxisome proliferator-activated receptor gamma
CHEMBL2459
EC50 5.39 5.39 4060.0 1
Unchecked
CHEMBL612545
EC50 5.33 5.33 4700.0 1
Cytochrome P450 2C9
CHEMBL3397
IC50 5.32 5.32 4780.0 1
Angiotensin-converting enzyme
CHEMBL1808
Ki 5.22 5.22 6000.0 1
Peroxisome proliferator-activated receptor gamma
CHEMBL235
IC50 4.91 4.91 12200.0 1
Bile salt export pump
CHEMBL6020
IC50 4.79 4.79 16200.0 3
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
IC50 4.77 4.77 16900.0 1
Multidrug and toxin extrusion protein 1
CHEMBL1743126
IC50 4.75 4.75 17900.0 1
ATP-binding cassette sub-family C member 4
CHEMBL1743128
IC50 4.44 4.44 36000.0 1
ATP-binding cassette sub-family C member 3
CHEMBL5918
IC50 4.22 4.22 60000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 3010.9 ng.hr.mL-1 Homo sapiens
AUC 3682.7 ng.hr.mL-1 Homo sapiens
AUC 3231.4 ng.hr.mL-1 Homo sapiens
AUC 3133.4 ng.hr.mL-1 Homo sapiens
AUC 3399.7 ng.hr.mL-1 Homo sapiens
AUC 2469.9 ng.hr.mL-1 Homo sapiens
AUC 3677.2 ng.hr.mL-1 Homo sapiens
AUC 1835.17 ng.hr.mL-1 Homo sapiens
CL 8.4 mL.min-1.kg-1 Homo sapiens
CL 8.3 mL.min-1.kg-1 Homo sapiens
CL 8.4 mL.min-1.kg-1 Homo sapiens
CL 8.4 mL.min-1.kg-1 Homo sapiens
CL 3.98 uL.min-1.(10^6cells)-1 Homo sapiens
CL 3.0 mL.min-1.g-1 Homo sapiens
CL 245.0 mL.min-1.kg-1 Homo sapiens
CL 163.33 mL.min-1.kg-1 Homo sapiens
CL 283.33 mL.min-1.kg-1 Homo sapiens
CL 231.67 mL.min-1.kg-1 Homo sapiens
CL 243.33 mL.min-1.kg-1 Homo sapiens
CL - mL.min-1.kg-1 Homo sapiens
CL 8.4 mL.min-1.kg-1 Homo sapiens
CL 20.0 mL.min-1.g-1 Homo sapiens
CL 21.7 mL.min-1.g-1 Homo sapiens
CL - - Homo sapiens
CL 17.8 mL.min-1.kg-1 Homo sapiens
CL 8.4 mL.min-1.kg-1 Homo sapiens
CL 9.93 mL.min-1.kg-1 Homo sapiens
CL 9.93 mL.min-1.kg-1 Homo sapiens
CL 298.33 mL.min-1.kg-1 Homo sapiens
CL 195.0 mL.min-1.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 A Ki = 0.23 nM 9.64 Displacement of [125I]SI-Ang2 from AT1 receptor in Sprague-Dawley rat liver memb... 20073471
Type-1 angiotensin II receptor A Ki = 0.23 nM 9.64 Displacement of [125I]-SI-Ang-2 from AT1 receptor in Rattus norvegicus Sprague-D... -
Type-2 angiotensin II receptor IC50 = 0.33 nM 9.48 Displacement of [125I]Sar1 Ile8-Ang 2 from angiotensin 2 AT2 receptor after 180 ... 22309912
Type-1 angiotensin II receptor IC50 = 0.49 nM 9.31 Displacement of [125I]Tyr4-Sar1,Ile8-Angiotensin II from human Angiotensin 1 rec... 23265881
Type-1 angiotensin II receptor IC50 = 0.49 nM 9.31 Displacement of [125I]Tyr4-Sar1,Ile8-Angiotensin II from human Angiotensin 1 rec... 21557540
Type-1 angiotensin II receptor IC50 = 1.0 nM 9.0 Displacement of [125I]Sar1 Ile8-Ang 2 from angiotensin 2 AT1 receptor after 180 ... 22309912
Type-1 angiotensin II receptor IC50 = 1.0 nM 9.0 Displacement of [125I]-Sar1Ile8-angiotensin 2 from angiotensin 2 AT1 receptor (u... 24007859
Type-1 angiotensin II receptor IC50 = 1.0 nM 9.0 Displacement of [125I]Sar1Ile8-Ang2 from angiotensin AT1 receptor after 180 mins... 22727371
Type-1 angiotensin II receptor IC50 = 2.0 nM 8.7 Antagonist activity at human AT1 receptor expressed in CHO cells measured after ... 24462665
Type-1 angiotensin II receptor IC50 = 2.0 nM 8.7 Inhibition of AT1 receptor (unknown origin) 31009912
Unchecked Ki = 2.75 nM 8.56 Displacement of [125I]-Sar1,Ile8-angiotensin 2 from AT1 receptor in Sprague-Dawl... 27017546
Type-1 angiotensin II receptor IC50 = 3.0 nM 8.52 Inhibition of AT1 receptor 20079636
Type-1 angiotensin II receptor B IC50 = 3.0 nM 8.52 Inhibition of specific binding of [125I]angiotensin-II to angiotensin 1 receptor... 8258826
Unchecked Ki = 3.7 nM 8.43 Binding affinity to angiotensin AT1 receptor in rat lung membranes 21071232
Unchecked IC50 = 3.8 nM 8.42 Displacement of [125I]-Sar1,Ile8-angiotensin 2 from AT1 receptor in Sprague-Dawl... 27017546
Type-1 angiotensin II receptor IC50 = 5.398 nM 8.27 GPCR PRESTO-Tango dose-response in antagonist mode with target: AGTR1 -
Plasmodium berghei IC50 = 25.0 nM 7.6 HARVARD: Inhibition of liver stage Plasmodium berghei infection in HepG2 cells 22586124
Plasmodium IC50 = 25.0 nM 7.6 Antimalarial activity against Plasmodium 32283298
Liver IC50 = 70.5 nM 7.15 Induction of mitochondrial dysfunction in Sprague-Dawley rat liver mitochondria ... 24799086
Cytochrome P450 2J2 Ki = 100.0 nM 7.0 Non-competitive inhibition of human recombinant CYP2J2 assessed as reduction in ... 23033255

Literature References

PubMed DOI Target Context # Activities
- 10.5281/zenodo.13943903 ADMET 89
31158845 10.1038/s41586-019-1291-3 ADMET 48
23118328 10.1124/dmd.112.046292 Homo sapiens 35
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
32017849 10.1021/acs.jmedchem.9b01440 Mus musculus 12
22275465 10.1124/dmd.111.043984 UDP-glucuronosyltransferase 1A3 12
32985885 10.1021/acs.jmedchem.0c01033 ADMET 11
- 10.6019/CHEMBL4689842 HEK-293T 10
22275465 10.1124/dmd.111.043984 Liver microsome 9
- 10.6019/CHEMBL4689842 U2OS 9
20070106 10.1021/jm901371v Homo sapiens 8
25740159 10.1016/j.bmcl.2015.02.013 No relevant target 8
- 10.6019/CHEMBL4689842 Fibroblast 8
22275465 10.1124/dmd.111.043984 ADMET 7
27560282 10.1016/j.ejmech.2016.07.072 Peroxisome proliferator-activated receptor gamma 6
32392051 10.1021/acs.jmedchem.0c00542 ADMET 6
23033255 10.1124/dmd.112.048264 Cytochrome P450 2J2 6
21282406 10.1124/dmd.110.037457 Nucleic Acid 5
20079636 10.1016/j.bmcl.2009.12.107 Peroxisome proliferator-activated receptor gamma 5
21282406 10.1124/dmd.110.037457 Plasma 5

Data from ChEMBL 36 via Core Engine