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)
1. Bolli MH, Boss C, Binkert C, Buchmann S, Bur D, Hess P, Iglarz M, Meyer S, Rein J, Rey M et al.. (2012)
The discovery of N-[5-(4-bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy]-4-pyrimidinyl]-N'-propylsulfamide (Macitentan), an orally active, potent dual endothelin receptor antagonist.
J Med Chem, 55 (17): 7849-61. [PMID:22862294]
2. Iglarz M, Binkert C, Morrison K, Fischli W, Gatfield J, Treiber A, Weller T, Bolli MH, Boss C, Buchmann S et al.. (2008)
Pharmacology of macitentan, an orally active tissue-targeting dual endothelin receptor antagonist.
J Pharmacol Exp Ther, 327 (3): 736-45. [PMID:18780830]