Macitentan

Macitentan
Clinical data
Trade names	Opsumit
Other names	ACT-064992
AHFS/Drugs.com	Monograph
MedlinePlus	a615033
License data	US DailyMed: Macitentan;
Pregnancy; category	AU: X (High risk);
Routes of; administration	By mouth
ATC code	C02KX04 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Metabolism	Hydrolysis, oxidation (CYP3A4)
Excretion	2/3 urine, 1/3 faeces
Identifiers
	IUPAC name N-[5-(4-Bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy]-4-pyrimidinyl]-N'-propylsulfamide;
CAS Number	441798-33-0;
PubChem CID	16004692;
DrugBank	DB08932;
ChemSpider	13134960;
UNII	Z9K9Y9WMVL;
KEGG	D10135;
ChEBI	CHEBI:76607;
ChEMBL	ChEMBL2103873;
CompTox Dashboard (EPA)	DTXSID50196063 ;
Chemical and physical data
Formula	C19H20Br2N6O4S
Molar mass	588.28 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Brc1ccc(cc1)c3c(ncnc3OCCOc2ncc(Br)cn2)NS(=O)(=O)NCCC;
	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); Key:JGCMEBMXRHSZKX-UHFFFAOYSA-N;

Macitentan, sold under the brand name Opsumit, is an endothelin receptor antagonist developed by Actelion and approved for the treatment of pulmonary arterial hypertension (PAH).^[4] Macitentan is a dual endothelin receptor antagonist, meaning that it acts as an antagonist of two endothelin (ET) receptor subtypes, ET_A and ET_B.^[4] However, macitentan has a 50-fold increased selectivity for the ET_A subtype compared to the ET_B subtype.^[5]

Macitentan was approved for medical use in the United States in October 2013.^[2]^[6] Macitentan is available as a generic medication.^[7]

^ "Prescription medicines: registration of new chemical entities in Australia, 2014". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 10 April 2023.
^ ^a ^b "Opsumit- macitentan tablet, film coated". DailyMed. 22 September 2020. Retrieved 24 October 2020.
^ "Opsumit EPAR". European Medicines Agency (EMA). 27 September 2011. Retrieved 6 August 2024.
^ ^a ^b Hong IS, Coe HV, Catanzaro LM (April 2014). "Macitentan for the treatment of pulmonary arterial hypertension". The Annals of Pharmacotherapy. 48 (4): 538–47. doi:10.1177/1060028013518900. PMID 24458948. S2CID 24720486.
^ Iglarz M, Binkert C, Morrison K, Fischli W, Gatfield J, Treiber A, et al. (December 2008). "Pharmacology of macitentan, an orally active tissue-targeting dual endothelin receptor antagonist". The Journal of Pharmacology and Experimental Therapeutics. 327 (3): 736–45. doi:10.1124/jpet.108.142976. PMID 18780830. S2CID 6315900.{{cite journal}}: CS1 maint: overridden setting (link)
^ "Actelion receives us fda approval of Opsumit (macitentan) for the treatment of pulmonary arterial hypertension" (Press release). Actelion. Archived from the original on 23 October 2013. Retrieved 22 October 2013.
^ "Macitentan: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Archived from the original on 10 May 2021. Retrieved 19 June 2021.

[1] "Prescription medicines: registration of new chemical entities in Australia, 2014". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 10 April 2023.

[Opsumit_FDA_label-2] "Opsumit- macitentan tablet, film coated". DailyMed. 22 September 2020. Retrieved 24 October 2020.

[Opsumit_EPAR-3] "Opsumit EPAR". European Medicines Agency (EMA). 27 September 2011. Retrieved 6 August 2024.

[Hong_2014-4] Hong IS, Coe HV, Catanzaro LM (April 2014). "Macitentan for the treatment of pulmonary arterial hypertension". The Annals of Pharmacotherapy. 48 (4): 538–47. doi:10.1177/1060028013518900. PMID 24458948. S2CID 24720486.

[Iglarz_2008-5] Iglarz M, Binkert C, Morrison K, Fischli W, Gatfield J, Treiber A, et al. (December 2008). "Pharmacology of macitentan, an orally active tissue-targeting dual endothelin receptor antagonist". The Journal of Pharmacology and Experimental Therapeutics. 327 (3): 736–45. doi:10.1124/jpet.108.142976. PMID 18780830. S2CID 6315900.{{cite journal}}: CS1 maint: overridden setting (link)

[6] "Actelion receives us fda approval of Opsumit (macitentan) for the treatment of pulmonary arterial hypertension" (Press release). Actelion. Archived from the original on 23 October 2013. Retrieved 22 October 2013.

[7] "Macitentan: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Archived from the original on 10 May 2021. Retrieved 19 June 2021.

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