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Compound Detail

CHEMBL9194

ATRASENTAN
🧪 Phase III
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🧪 Phase III
CCCCN(CCCC)C(=O)CN1C[C@H](c2ccc3c(c2)OCO3)[C@@H](C(=O)O)[C@@H]1c1ccc(OC)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL9194
Name ATRASENTAN
Phase Phase III
Structure Type MOL
InChI Key MOTJMGVDPWRKOC-QPVYNBJUSA-N

Known Names

Atrasentan
7
Targets
30
Activities
3
Assay Types
12
PK Parameters
20
Publications
1
Known Names
5
Indications

Molecular Properties

510.6
MW (Da)
4.69
ALogP
6
HBA
1
HBD
88.5
PSA (Ų)
0.44
QED
1
Ro5 Violations
12
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -entan
USAN Year 2000

Extended Properties

Molecular Formula C29H38N2O6
MW 510.63
Aromatic Rings 2
Heavy Atoms 37
NP-Likeness -0.35

Indications

Diabetic Nephropathies Glomerulonephritis, IGA Prostatic Neoplasms Prostatic Neoplasms, Castration-Resistant Renal Insufficiency, Chronic

Activity Summary

IC50 22 meas. best 10.47
Ki 6 meas. best 10.47
Kd 2 meas. best 8.6

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Endothelin-1 receptor
CHEMBL252
 IC50 10.47 10.125 0.0 8
Endothelin-1 receptor
CHEMBL252
 Ki 10.47 10.47 0.0 3
Endothelin-1 receptor
CHEMBL4566
 Ki 10.47 10.4 0.0 2
Endothelin receptor
CHEMBL2111453
 IC50 10.4 10.4 0.0 1
Endothelin-1 receptor
CHEMBL4566
 IC50 10.1 9.4633 0.1 6
Rattus norvegicus
CHEMBL376
 Kd 8.6 8.6 2.5 1
Endothelin receptor type B
CHEMBL1785
 IC50 7.2 6.905 63.3 4
Endothelin receptor type B
CHEMBL1785
 Ki 7.2 7.2 63.3 1
Endothelin receptor type B
CHEMBL3949
 IC50 6.96 6.6533 110.0 3
Oryctolagus cuniculus
CHEMBL374
 Kd 6.1 6.1 794.3 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 10666.67 ng.hr.mL-1 Rattus norvegicus
AUC 5833.33 ng.hr.mL-1 Rattus norvegicus
AUC 7.36 ug ml-1 -
Cmax 6266.77 nM Rattus norvegicus
Cmax 6736.78 nM -
F 70.0 % Rattus norvegicus
F 68.0 % Rattus norvegicus
F 60.2 % Eutheria
T1/2 3.5 hr Rattus norvegicus
T1/2 3.5 hr -
T1/2 3.5 hr -
T1/2 6.2 hr -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Endothelin-1 receptor IC50 = 0.034 nM 10.47 Binding ability determined by the displacement of [125I]ET1 from the human endot... 10479299
Endothelin-1 receptor Ki = 0.034 nM 10.47 Binding affinity towards Endothelin A receptor 15055997
Endothelin-1 receptor Ki = 0.034 nM 10.47 Inhibitory activity against human Endothelin A receptor in chinese hamster ovary... 8676339
Endothelin-1 receptor Ki = 0.034 nM 10.47 Displacement of [125I]ET-1 from human ET-A receptor expressed in CHO cell membra... 27266371
Endothelin-1 receptor Ki = 0.034 nM 10.47 Binding affinity to ETA receptor (unknown origin) assessed as inhibition constan... 12193066
Endothelin-1 receptor IC50 = 0.034 nM 10.47 Ability to displace endothelin ([125I]ET1) from human Endothelin A receptor 9379441
Endothelin receptor IC50 = 0.04 nM 10.4 Inhibition of phosphoinositol hydrolysis of MMQ cells. 8676339
Endothelin-1 receptor Ki = 0.047 nM 10.33 binding affinity against human Endothelin A receptor 11689084
Endothelin-1 receptor IC50 = 0.055 nM 10.26 Displacement of [125I]ET-1 from human ET-A receptor expressed in CHO cell membra... 27266371
Endothelin-1 receptor IC50 = 0.055 nM 10.26 Antagonist activity at ETA receptor (unknown origin) 12193066
Endothelin-1 receptor IC50 = 0.059 nM 10.23 Antagonist activity at ETA receptor (unknown origin) assessed as inhibition of p... 12193066
Endothelin-1 receptor IC50 = 0.08 nM 10.1 Binding affinity towards human Endothelin A receptor (hET -A) 10479298
Endothelin-1 receptor IC50 = 0.08 nM 10.1 Inhibitory activity against human Endothelin A receptor 11689084
Endothelin-1 receptor IC50 = 0.2 nM 9.7 Antagonist activity at ETA receptor (unknown origin) assessed as inhibition of a... 12193066
Endothelin-1 receptor IC50 = 0.31 nM 9.51 Ability to displace [125I]ET1 from the rat endothelin A receptor expressed in ra... 15139753
Endothelin-1 receptor IC50 = 0.31 nM 9.51 Inhibitory activity against the Endothelin A receptor of rat MMQ cells 8676339
Endothelin-1 receptor IC50 = 0.31 nM 9.51 Displacement of [125I]ET-1 from Endothelin A receptor 15055997
Endothelin-1 receptor IC50 = 0.36 nM 9.44 Binding affinity against Endothelin A receptor in MMQ cells in rat 11689084
Endothelin-1 receptor IC50 = 0.4 nM 9.4 Binding affinity towards endothelin A receptor in prolactin secreting rat pituit... 9022798
Endothelin-1 receptor IC50 = 1.5 nM 8.82 In vitro ability to inhibit specific [125I]ET1 binding to rat aorta membranes En... 9873432

Literature References

PubMed DOI Target Context # Activities
11689084 10.1021/jm010237l ADMET 5
12193066 10.1042/cs103s107s Endothelin-1 receptor 4
11689084 10.1021/jm010237l Endothelin-1 receptor 3
12193066 10.1042/cs103s107s Endothelin receptor type B 3
9022798 10.1021/jm960077r Rattus norvegicus 3
15055997 10.1021/jm030528p Rattus norvegicus 2
27266371 10.1021/acs.jmedchem.5b01781 Endothelin-1 receptor 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
11689084 10.1021/jm010237l Endothelin receptor type B 2
8676339 10.1021/jm9505369 Endothelin-1 receptor 2
9022798 10.1021/jm960077r ADMET 2
15055997 10.1021/jm030528p Endothelin-1 receptor 2
8676339 10.1021/jm9505369 Endothelin receptor type B 1
8676339 10.1021/jm9505369 Endothelin receptor 1
10479298 10.1021/jm990170q Endothelin-1 receptor 1
10479299 10.1021/jm990171i Endothelin-1 receptor 1
12193066 10.1042/cs103s107s Unchecked 1
9022798 10.1021/jm960077r Endothelin-1 receptor 1
9379441 10.1021/jm970101g ADMET 1
9379441 10.1021/jm970101g Endothelin-1 receptor 1

Data from ChEMBL 36 via Core Engine