AMBRISENTAN

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC C02KX02
UNII HW6NV07QEC
EPA CompTox DTXSID4046282

Structure

InChI Key OUJTZYPIHDYQMC-LJQANCHMSA-N
Smiles COC(c1ccccc1)(c1ccccc1)[C@H](Oc1nc(C)cc(C)n1)C(=O)O
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C22H22N2O4
Molecular Weight 378.43
AlogP 3.52
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 7.0
Polar Surface Area 81.54
Molecular species ACID
Aromatic Rings 3.0
Heavy Atoms 28.0

Metabolites Network

visNetwork

Bioactivity

Mechanism of Action Action Reference
Endothelin receptor, ET-A/ET-B antagonist ANTAGONIST DailyMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Auxiliary transport protein Slow voltage-gated potassium channel accessory protein family
- 63096 - - -
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 63096 - - -
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Endothelin receptor
- 1-22 81-2344 - 43
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group I Nuclear hormone receptor subfamily 1 group I member 2
31600-31600 - - - -
Assay Description Organism Bioactivity Reference
Antagonist activity towards human recombinant Endothelin A receptor expressed in chinese hamster ovary (CHO) cells determined using [125I]ET1 as radioligand None 21.7 nM
Inhibitory potency at native endothelin A and endothelin B receptors by inhibiting endothelin-1 contractions of rat aortic rings Homo sapiens 81.28 nM
Inhibition of endothelin A receptor in New Zealand white rabbit aortic rings assessed as inhibition of endothelin-1-induced vascular contraction at 10'-6 M Oryctolagus cuniculus 43.23 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens -9.97 %
Displacement of [125I]-ET-1 from human ETA receptor expressed in CHO cell membranes after 2 hrs by scintillation counting Homo sapiens 1.0 nM
Displacement of [125I]-ET-1 from human ETB receptor expressed in CHO cell membranes after 2 hrs by scintillation counting Homo sapiens 195.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 24.29 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 5.946 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.08 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.16 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.08 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.16 %

Related Entries

Cross References

Resources Reference
ChEBI 135949
ChEMBL CHEMBL1111
DrugBank DB06403
DrugCentral 4337
FDA SRS HW6NV07QEC
Guide to Pharmacology 3951
KEGG D07077
PubChem 6918493
SureChEMBL SCHEMBL3679
ZINC ZINC000000538627
CONTENTS