AVOSENTAN

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Search structure


Synonyms	Avosentan RO 67-0565 RO-67-0565 Ro670565 SPP-301 SPP301
Status
Molecule Category	UNKNOWN
UNII	L94KSX715K
EPA CompTox	DTXSID30183330


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	YBWLTKFZAOSWSM-UHFFFAOYSA-N
Smiles	COc1ccccc1Oc1c(NS(=O)(=O)c2ccc(C)cn2)nc(-c2ccncc2)nc1OC
InChI	InChI=1S/C23H21N5O5S/c1-15-8-9-19(25-14-15)34(29,30)28-22-20(33-18-7-5-4-6-17(18)31-2)23(32-3)27-21(26-22)16-10-12-24-13-11-16/h4-14H,1-3H3,(H,26,27,28)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C23H21N5O5S
Molecular Weight	479.52
AlogP	3.85
Hydrogen Bond Acceptor	9.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	8.0
Polar Surface Area	125.42
Molecular species	ACID
Aromatic Rings	4.0
Heavy Atoms	34.0

Bioactivity

Mechanism of Action	Action	Reference
Endothelin receptor ET-A antagonist	ANTAGONIST	PubMed Other


Protein: Endothelin receptor ET-A Description: Endothelin-1 receptor Organism : Homo sapiens P25101 ENSG00000151617

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Endothelin receptor	-	1-3	-	-	-

Assay Description	Organism	Bioactivity	Reference
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	-7.75 %
Displacement of radioligand from ETB receptor in human placenta cell membranes	Homo sapiens	600.0 nM
Displacement of 125I-ET1 from ETA receptor (unknown origin) expressed in CHO cells	Homo sapiens	1.4 nM
Antagonist activity at ETA receptor (unknown origin) in presence of ET1	Homo sapiens	3.1 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	20.61 %
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	0.03 %		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	0.03 %

Related Entries

Cross References

Resources	Reference
ChEMBL	CHEMBL3989834
FDA SRS	L94KSX715K
Guide to Pharmacology	8260
PubChem	9912992
SureChEMBL	SCHEMBL2742679
ZINC	ZINC000000602818

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).