Macitentan

An orally administered dual endothelin receptor antagonist used for the treatment of pulmonary arterial hypertension (PAH). Macitentan blocks endothelin ETA and ETB receptors, reducing endothelin-1-mediated vasoconstriction, vascular smooth muscle proliferation, and pathological pulmonary vascular remodeling. It improves exercise capacity and reduces the risk of clinical worsening in patients with PAH. Its active metabolite, aprocitentan, contributes to sustained endothelin receptor antagonism. Important adverse effects include anemia, fluid retention, and embryo-fetal toxicity

CAS Number: 441798-33-0

Molecular Mass: 588.3 g/mol

Formula: C₁₉H₂₀Br₂N₆O₄S

Smiles: CCCNS(=O)(=O)Nc1ncnc(OCCOc2ncc(Br)cn2)c1-c1ccc(Br)cc1

Synonymes:

Macitentan, 441798-33-0, Opsumit, ACT-064992, Actelion-1, ACT 064992, ACT064992, macitentanum, Z9K9Y9WMVL, CHEBI:76607, DTXSID50196063, OPSYNVI COMPONENT MACITENTAN, {[5-(4-BROMOPHENYL)-6-{2-[(5-BROMOPYRIMIDIN-2-YL)OXY]ETHOXY}PYRIMIDIN-4-YL]SULFAMOYL}(PROPYL)AMINE, n-(5-(4-bromophenyl)-6-(2-(5-bromopyrimidin-2-yloxy)ethoxy)pyrimidin-4-yl)-n'-propylaminosulfonamide, N-(5-(4-BROMOPHENYL)-6-(2-((5-BROMOPYRIMIDIN-2-YL)OXI)ETHOXY)PYRIMIDIN-4-YL)-N'-PROPYLSULFURIC DIAMIDE, N-(5-(4-Bromophenyl)-6-(2-((5-bromopyrimidin-2-yl)oxy)ethoxy)pyrimidin-4-yl)-N'-propylsulfamide, N-[5-(4-bromophenyl)-6-{2-[(5-bromopyrimidin-2-yl)oxy]ethoxy}pyrimidin-4-yl]-N'-propylsulfuric diamide, ((5-(4-bromophenyl)-6-(2-((5-bromopyrimidin-2-yl)oxy)ethoxy)pyrimidin-4-yl)sulfamoyl)(propyl)amine, N-(5-(4-Bromophenyl)-6-(2-((5-bromopyrimidin-2-yl)oxy)ethoxy)pyrimidin-4-yl)-N'-propylsulfuric diamide, RefChem:58979, C02KX04, DTXCID60118554, N-[5-(4-Bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy]-4-pyrimidinyl]-N'-propylsulfamide, N-(5-(4-Bromophenyl)-6-(2-((5-bromo-2-pyrimidinyl)oxy)ethoxy)-4-pyrimidinyl)-N'-propylsulfamide, MFCD17167076, 5-(4-bromophenyl)-6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-N-(propylsulfamoyl)pyrimidin-4-amine, C19H20Br2N6O4S, Macitentan [INN], Macitentan [USAN:INN], UNII-Z9K9Y9WMVL, Sulfamide, N-[5-(4-bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy]-4-pyrimidinyl]-N'-propyl-, N-[5-(4-Bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy]-4-pyrimidinyl]-N'-propylsulfamide, ACT 064992, Macitentan, Opsumit, Propylsulfamic acid N-[5-(4-bromophenyl)-6-[2-[(5-bromopyrimidin-2-yl)oxy]ethoxy]pyrimidin-4-yl]amide, Opsumit (TN), Macitentan (Standard), MACITENTAN [MI], MACITENTAN [JAN], Macitentan (JAN/USAN), MACITENTAN [USAN], MACITENTAN [VANDF], A1D5I, MACITENTAN [WHO-DD], MLS006011174, GTPL7352, Macitentan - Bio-X trade mark, orb1305317, SCHEMBL1445625, CHEMBL2103873, MACITENTAN [ORANGE BOOK], SCHEMBL29378853, EX-A544, JGCMEBMXRHSZKX-UHFFFAOYSA-N, GLXC-90056, HMS3653N06, HMS3747E09, HMS5086O05, cas:441798-33-0, Macitentan, IAC42805, BDBM50395626, EBC-27358, HY-14184R, s8051, AKOS024463406, CCG-270155, CS-0686, DB08932, FM65071, SB14841, Macitentan (Actelion-1,ACT-064992), NCGC00346456-01, NCGC00346456-05, AC-30102, AS-74590, BM162771, HY-14184, N-[5-(4-bromophenyl)-6-{2-[(5-bromopyrimidin-2-yl)oxy]ethoxy}pyrimidin-4-yl]-N'- propylsulfamide, SMR004702943, Macitentan (Actelion-1,ACT-064992)?, DB-070519, NS00072551, SW219473-1, ACT 064992, ACT-064992, D10135, Opsynvi (combination of macitentan + tadalafil), EN300-7404089, Q6724151, BRD-K48812570-001-02-3, BRD-K48812570-001-03-1, 5-(p-Bromophenyl)-6-[2-(5-bromo-2-pyrimidinyloxy)ethoxy]-4-(propylaminosulfonylamino)pyrimidine, N-[5-(4-Bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)-oxy]ethoxy]-4-pyrimidinyl]-N'-propylsulfamide, Sulfamide, N-[5-(4-bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy]-4-pyrimidinyl]-N'-propyl-

Bioactivity: Dual endothelin receptor antagonist (ERA); endothelin ETA and ETB receptor blocker; pulmonary vasodilator

Solubility in Different Solvents

Solvent	Temperature [K]	Crystal form	Solubility [mg/mL]	Reference
Ethanol	273.15	-	0.66	[135]
Ethanol	278.15	-	0.902	[135]
Ethanol	283.15	-	1.192	[135]
Ethanol	288.15	-	1.53	[135]
Ethanol	293.15	-	1.896	[135]
Ethanol	298.15	-	2.348	[135]
Ethanol	303.15	-	2.923	[135]
Ethanol	308.15	-	3.62	[135]
Ethanol	313.15	-	4.518	[135]
Ethyl acetate	273.15	-	20.97	[135]
Ethyl acetate	278.15	-	25.02	[135]
Ethyl acetate	283.15	-	29.56	[135]
Ethyl acetate	288.15	-	35.15	[135]
Ethyl acetate	293.15	-	41.2	[135]
Ethyl acetate	298.15	-	47.73	[135]
Ethyl acetate	303.15	-	55.16	[135]
Ethyl acetate	308.15	-	63.71	[135]
Ethyl acetate	313.15	-	72.41	[135]
Isopropanol	273.15	-	0.369	[135]
Isopropanol	278.15	-	0.461	[135]
Isopropanol	283.15	-	0.583	[135]
Isopropanol	288.15	-	0.712	[135]
Isopropanol	293.15	-	0.8768	[135]
Isopropanol	298.15	-	1.078	[135]
Isopropanol	303.15	-	1.308	[135]
Isopropanol	308.15	-	1.559	[135]
Isopropanol	313.15	-	1.85	[135]
Methanol	273.15	-	1.13	[135]
Methanol	278.15	-	1.612	[135]
Methanol	283.15	-	2.131	[135]
Methanol	288.15	-	2.718	[135]
Methanol	293.15	-	3.37	[135]
Methanol	298.15	-	4.101	[135]
Methanol	303.15	-	5.139	[135]
Methanol	308.15	-	6.607	[135]
Methanol	313.15	-	8.54	[135]

Molecule 3D descriptors

Descriptor	Value
PMI1	4487.4645
PMI2	11423.5665
PMI3	15060.3621
NPR1	0.2980
NPR2	0.7585
RadiusOfGyration	5.1307
InertialShapeFactor	0.0002
Eccentricity	0.9546
Asphericity	0.3610
SpherocityIndex	0.1697
PBF	0.9092