APROCITENTAN

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Synonyms	ACT-132577 Act-132577 Aprocitentan Macitentan metabolite m6
Status
Molecule Category	UNKNOWN
UNII	MZI81HV01P


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

Structure


InChI Key	DKULOVKANLVDEA-UHFFFAOYSA-N
Smiles	NS(=O)(=O)Nc1ncnc(OCCOc2ncc(Br)cn2)c1-c1ccc(Br)cc1
InChI	InChI=1S/C16H14Br2N6O4S/c17-11-3-1-10(2-4-11)13-14(24-29(19,25)26)22-9-23-15(13)27-5-6-28-16-20-7-12(18)8-21-16/h1-4,7-9H,5-6H2,(H2,19,25,26)(H,22,23,24)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C16H14Br2N6O4S
Molecular Weight	546.2
AlogP	2.53
Hydrogen Bond Acceptor	8.0
Hydrogen Bond Donor	2.0
Number of Rotational Bond	8.0
Polar Surface Area	142.21
Molecular species	NEUTRAL
Aromatic Rings	3.0
Heavy Atoms	29.0

Bioactivity

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

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	-	3-3	-	-	-

Assay Description	Organism	Bioactivity	Reference
Displacement of [I125]ET1 from recombinant ETB receptor expressed in CHO cells after 2 hrs by TopCount analysis	None	987.0 nM
Displacement of [I125]ET1 from recombinant ETA receptor expressed in CHO cells after 2 hrs by TopCount analysis	None	3.4 nM
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	-1.01 %
Displacement of [125I]-ET-1 from human ETA receptor expressed in CHO cell membranes after 2 hrs by scintillation counting	Homo sapiens	3.4 nM
Displacement of [125I]-ET-1 from human ETB receptor expressed in CHO cell membranes after 2 hrs by scintillation counting	Homo sapiens	987.0 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	8.054 %
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	0.0 %		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	0.0 %

Related Entries

Cross References

Resources	Reference
ChEBI	76609
ChEMBL	CHEMBL2165326
DrugBank	DB15059
FDA SRS	MZI81HV01P
Guide to Pharmacology	10070
PubChem	25099191
SureChEMBL	SCHEMBL3646065
ZINC	ZINC000095553608

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).