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Compound Detail

CHEMBL1111

AMBRISENTAN
💊 Approved Drug
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💊 Approved Drug
COC(c1ccccc1)(c1ccccc1)[C@H](Oc1nc(C)cc(C)n1)C(=O)O

Basic Information

ChEMBL ID CHEMBL1111
Name AMBRISENTAN
Phase Approved
Structure Type MOL
InChI Key OUJTZYPIHDYQMC-LJQANCHMSA-N
Therapeutic ✓ Yes

Known Names

Ambrisentan Ambrisentan mylan GSK-1325760 GSK-1325760A GSK1325760 GSK1325760A Letairis LU-208075 Volibris
5
Targets
16
Activities
3
Assay Types
0
PK Parameters
20
Publications
9
Known Names
12
Indications
1
Mechanisms

Molecular Properties

378.4
MW (Da)
3.52
ALogP
5
HBA
1
HBD
81.5
PSA (Ų)
0.68
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2007
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -entan

Extended Properties

Molecular Formula C22H22N2O4
MW 378.43
Aromatic Rings 3
Heavy Atoms 28
NP-Likeness -0.17

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Endothelin receptor, ET-A/ET-B antagonist ANTAGONIST Endothelin receptor, ET-A/ET-B

Indications

Familial Primary Pulmonary Hypertension Hypertension Hypertension, Pulmonary Hypertension, Pulmonary Pulmonary Arterial Hypertension Idiopathic Pulmonary Fibrosis Vascular Diseases Altitude Sickness Asthma Hypoplastic Left Heart Syndrome Severe Acute Respiratory Syndrome Anemia, Sickle Cell

ATC Classification

C02KX02
ambrisentan
Level 1: CARDIOVASCULAR SYSTEM
Level 2: ANTIHYPERTENSIVES

Drug Warnings

Black Box Warning
teratogenicity
Country: United States

Activity Summary

IC50 12 meas. best 9.0
EC50 2 meas. best 4.5
Kd 2 meas. best 7.09

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Endothelin-1 receptor
CHEMBL252
IC50 9.0 8.33 1.0 2
Endothelin receptor
CHEMBL2111453
Kd 7.09 6.36 81.3 2
Endothelin receptor type B
CHEMBL1785
IC50 6.71 6.315 195.0 2
Nuclear receptor subfamily 1 group I member 2
CHEMBL3401
EC50 4.5 4.5 31600.0 2
Voltage-gated potassium channel, IKs; KCNQ1(Kv7.1)/KCNE1(MinK)
CHEMBL2221347
IC50 4.2 4.2 63095.7 1

Activity Data Samples

Top measurements by pChEMBL value

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5724801 U2OS 304
- 10.6019/CHEMBL5724801 HEK-293T 304
- 10.6019/CHEMBL5058577 Fibroblast 304
- 10.6019/CHEMBL5058577 U2OS 304
- 10.6019/CHEMBL5058577 HEK-293T 304
- 10.6019/CHEMBL5724801 Fibroblast 304
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
20966043 10.1124/dmd.110.035105 Nuclear receptor subfamily 1 group I member 2 6
- 10.6019/CHEMBL5209801 Alpha-2A adrenergic receptor 5
- 10.6019/CHEMBL5209801 Sphingosine 1-phosphate receptor 1 5
- 10.6019/CHEMBL5058564 Fibroblast 5
- 10.6019/CHEMBL5209801 Free fatty acid receptor 4 5
- 10.6019/CHEMBL5209801 CX3C chemokine receptor 1 5
- 10.6019/CHEMBL5209801 Glucose-dependent insulinotropic receptor 5
- 10.6019/CHEMBL5209801 Type-1 angiotensin II receptor 5
- 10.6019/CHEMBL5209801 Apelin receptor 5
- 10.6019/CHEMBL5209801 N-formyl peptide receptor 2 5
- 10.6019/CHEMBL5209801 C5a anaphylatoxin chemotactic receptor 1 5
- 10.6019/CHEMBL5209801 Adhesion G-protein coupled receptor F1 5
- 10.6019/CHEMBL5209801 Beta-2 adrenergic receptor 5

Data from ChEMBL 36 via Core Engine