MACITENTAN

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Search structure


Trade Names	OPSUMIT
Synonyms	ACT 064992 ACT-064992 Macitentan Opsumit
Status
Molecule Category	UNKNOWN
ATC	C02KX04
UNII	Z9K9Y9WMVL
EPA CompTox	DTXSID50196063


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

Structure


InChI Key	JGCMEBMXRHSZKX-UHFFFAOYSA-N
Smiles	CCCNS(=O)(=O)Nc1ncnc(OCCOc2ncc(Br)cn2)c1-c1ccc(Br)cc1
InChI	InChI=1S/C19H20Br2N6O4S/c1-2-7-26-32(28,29)27-17-16(13-3-5-14(20)6-4-13)18(25-12-24-17)30-8-9-31-19-22-10-15(21)11-23-19/h3-6,10-12,26H,2,7-9H2,1H3,(H,24,25,27)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C19H20Br2N6O4S
Molecular Weight	588.28
AlogP	3.57
Hydrogen Bond Acceptor	8.0
Hydrogen Bond Donor	2.0
Number of Rotational Bond	11.0
Polar Surface Area	128.22
Molecular species	NEUTRAL
Aromatic Rings	3.0
Heavy Atoms	32.0

Bioactivity

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

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
Displacement of [I125]ET1 from recombinant ETB receptor expressed in CHO cells after 2 hrs by TopCount analysis	None	391.0 nM
Displacement of [I125]ET1 from recombinant ETA receptor expressed in CHO cells after 2 hrs by TopCount analysis	None	0.5 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	-1.71 %
Antagonist activity at human ETB receptor expressed in CHO cells in presence of ET1	Homo sapiens	987.0 nM
Displacement of [125I]-ET-1 from human ETA receptor expressed in CHO cell membranes after 2 hrs by scintillation counting	Homo sapiens	0.5 nM
Displacement of [125I]-ET-1 from human ETB receptor expressed in CHO cell membranes after 2 hrs by scintillation counting	Homo sapiens	391.0 nM
Antagonist activity at human ETA receptor expressed in CHO cells in presence of ET1	Homo sapiens	3.4 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	17.13 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	10.96 %
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	0.15 %		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	-0.1 %		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	-0.1 %		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	0.15 %

Related Entries

Cross References

Resources	Reference
ChEBI	76607
ChEMBL	CHEMBL2103873
DrugBank	DB08932
DrugCentral	4809
FDA SRS	Z9K9Y9WMVL
Guide to Pharmacology	7352
KEGG	D10135
PubChem	16004692
SureChEMBL	SCHEMBL1445625
ZINC	ZINC000043202140

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).