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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1111
CHEMBL1111
Compound Name AMBRISENTAN
ChEMBL Synonyms VOLIBRIS | AMBRISENTAN | LETAIRIS
Max Phase 4 (Approved)
Trade Names LETAIRIS | VOLIBRIS
Molecular Formula C22H22N2O4

Additional synonyms for CHEMBL1111 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES COC([C@H](Oc1nc(C)cc(C)n1)C(=O)O)(c2ccccc2)c3ccccc3
Standard InChI InChI=1S/C22H22N2O4/c1-15-14-16(2)24-21(23-15)28-19(20(25)26 ...
Download InChI
Standard InChI Key OUJTZYPIHDYQMC-LJQANCHMSA-N

Sources

  • British National Formulary
  • FDA Approval Packages
  • HeCaToS Compounds
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL1111

Molecule Features

CHEMBL1111 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Endothelin receptor, ET-A/ET-B antagonist Endothelin receptor, ET-A/ET-B DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Idiopathic Pulmonary FibrosisD054990EFO:0000768idiopathic pulmonary fibrosis3ClinicalTrials
Vascular DiseasesD014652EFO:0004264vascular disease3ClinicalTrials
Altitude SicknessD000532EFO:1000782altitude sickness2ClinicalTrials
Anemia, Sickle CellD000755Orphanet:232Sickle cell anemia1ClinicalTrials
HypertensionD006973EFO:0000537hypertension4ATC
ClinicalTrials
Hypertension, PulmonaryD006976EFO:0001361pulmonary hypertension3ClinicalTrials
AsthmaD001249EFO:0000270asthma2ClinicalTrials
Familial Primary Pulmonary HypertensionD065627Orphanet:422Idiopathic and/or familial pulmonary arterial hypertension4DailyMed

Clinical Data

ClinicalTrials.gov AMBRISENTAN
The Cochrane Collaboration AMBRISENTAN

Metabolites for CHEMBL1111

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Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL1111. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL1785 Endothelin receptor ET-B Homo sapiens 1.000
CHEMBL252 Endothelin receptor ET-A Homo sapiens 1.000
CHEMBL3622 Cytochrome P450 2C19 Homo sapiens 0.390
CHEMBL1821 Muscarinic acetylcholine receptor M4 Homo sapiens 0.302
CHEMBL3397 Cytochrome P450 2C9 Homo sapiens 0.267
CHEMBL4159 Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Homo sapiens 0.264



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL1785 Endothelin receptor ET-B Homo sapiens 1.000
CHEMBL252 Endothelin receptor ET-A Homo sapiens 1.000
CHEMBL3397 Cytochrome P450 2C9 Homo sapiens 0.494
CHEMBL3622 Cytochrome P450 2C19 Homo sapiens 0.233

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
378.4 378.158 3.52 7 81.54 ACID


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
5 1 0 6 1 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
.97 2.84 2.82 -.92 3 28 0.68

Structural Alerts

There are no structural alerts for CHEMBL1111

Compound Cross References

ATC C - CARDIOVASCULAR SYSTEM
C02 - ANTIHYPERTENSIVES
C02K - OTHER ANTIHYPERTENSIVES
C02KX - Antihypertensives for pulmonary arterial hypertension
C02KX02 - ambrisentan

ChemSpider ChemSpider:OUJTZYPIHDYQMC-LJQANCHMSA-N
DailyMed ambrisentan
PubChem SID: 144205520 SID: 170465143
Wikipedia Ambrisentan

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1111



ACToR 177036-94-1
BindingDB 50146710
ChEBI 135949
ChemicalBook CB71011125
DrugBank DB06403
DrugCentral 4337
eMolecules 36367209
EPA CompTox Dashboard DTXSID4046282
FDA SRS HW6NV07QEC
Guide to Pharmacology 3951
IBM Patent System 089E6328BE9ABC47B44552ACF7919442
LINCS LSM-45789
MolPort MolPort-005-942-453
Nikkaji J2.651.033C
PubChem 6918493
PubChem: Drugs of the Future 12015371
PubChem: Thomson Pharma 14779987
Selleck ambrisentan
SureChEMBL SCHEMBL3679
ZINC ZINC000000538627

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/OUJTZYPIHDYQMC-LJQANCHMSA-N spacer
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