ambrisentan   Click here for help

GtoPdb Ligand ID: 3951

Synonyms: Letairis®
Approved drug
ambrisentan is an approved drug (FDA (2007), EMA (2008))
Compound class: Synthetic organic
Comment: Ambrisentan is an endothelin receptor antagonist, with selectivity for the type A endothelin receptor (ETA).
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: ambrisentan

ambrisentan is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 81.54
Molecular weight 378.16
XLogP 3.67
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES COC(C(C(=O)O)Oc1nc(C)cc(n1)C)(c1ccccc1)c1ccccc1
Isomeric SMILES COC([C@@H](C(=O)O)Oc1nc(C)cc(n1)C)(c1ccccc1)c1ccccc1
InChI InChI=1S/C22H22N2O4/c1-15-14-16(2)24-21(23-15)28-19(20(25)26)22(27-3,17-10-6-4-7-11-17)18-12-8-5-9-13-18/h4-14,19H,1-3H3,(H,25,26)/t19-/m1/s1
InChI Key OUJTZYPIHDYQMC-LJQANCHMSA-N
No information available.
Summary of Clinical Use Click here for help
Approved to treat pulmonary arterial hypertension (PAH).
Ambrisentan is being evaluated in Phase 3 clinical trial for the additional indication chronic thromboembolic pulmonary hypertension.

COVID-19: In response to the SARS-CoV-2 pandemic, clinical trials were initiated to address the potential of endothelin receptor antagonism as a treatment for endothelial cell damage and dysfunction in the blood vessels (in the lungs and other organs) that occurs during SARS-CoV-2 infection.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Ambrisentan is a selective endothelin receptor A (ETA) antagonist. Antagonism of endothelin binding to ETA decreases vasoconstriction in the smooth muscle of the lungs and reduces pulmonary blood pressure.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT04393246 mulTi-Arm Therapeutic Study in Pre-ICu Patients Admitted With Covid-19 - Experimental Drugs and Mechanisms Phase 2/Phase 3 Interventional Cambridge University Hospitals NHS Foundation Trust
NCT04771000 A Study of Micro Dose Ambrisentan in Hospitalized Patients With Respiratory Insufficiency Due to COVID-19 Phase 2 Interventional Noorik Biopharmaceuticals AG