macitentan   Click here for help

GtoPdb Ligand ID: 7352

Synonyms: ACT-064992 | Opsumit®
Approved drug
macitentan is an approved drug (FDA and EMA (2013))
Compound class: Synthetic organic
Comment: Macitentan is an endothelin receptor antagonist (ERA). It exhibits approximately 50-fold selectivity for the ETA receptor over the ETB receptor [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 2
Rotatable bonds 11
Topological polar surface area 136.6
Molecular weight 585.96
XLogP 4.15
No. Lipinski's rules broken 1
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Canonical SMILES CCCNS(=O)(=O)Nc1ncnc(c1c1ccc(cc1)Br)OCCOc1ncc(cn1)Br
Isomeric SMILES CCCNS(=O)(=O)Nc1ncnc(c1c1ccc(cc1)Br)OCCOc1ncc(cn1)Br
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)
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Summary of Clinical Use Click here for help
Macitentan is approved for the treatment of pulmonary arterial hypertension (PAH).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Macitentan is an endothelin receptor antagonist. It blocks endothelin-1-induced activation of endothelin A and B receptors (ETA and ETB respectively) located on blood vessels and smooth muscle, and reduces fibrosis and vasoconstriction by modulating the renin-angiotensin system.
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