Macitentan

Macitentan
Clinical data
Trade namesOpsumit
Other namesACT-064992
AHFS/Drugs.comMonograph
MedlinePlusa615033
License data
Pregnancy
category
  • AU: X (High risk)
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
MetabolismHydrolysis, oxidation (CYP3A4)
Excretion2/3 urine, 1/3 faeces
Identifiers
  • N-[5-(4-Bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy]-4-pyrimidinyl]-N'-propylsulfamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H20Br2N6O4S
Molar mass588.28 g·mol−1
3D model (JSmol)
  • Brc1ccc(cc1)c3c(ncnc3OCCOc2ncc(Br)cn2)NS(=O)(=O)NCCC
  • 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).[5] Macitentan is a dual endothelin receptor antagonist, meaning that it acts as an antagonist of two endothelin (ET) receptor subtypes, ETA and ETB.[5] However, macitentan has a 50-fold increased selectivity for the ETA subtype compared to the ETB subtype.[6]

Macitentan was approved for medical use in the United States in October 2013.[3][7] Macitentan is available as a generic medication.[8]

  1. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  2. ^ "Prescription medicines: registration of new chemical entities in Australia, 2014". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 10 April 2023.
  3. ^ a b "Opsumit- macitentan tablet, film coated". DailyMed. 22 September 2020. Retrieved 24 October 2020.
  4. ^ "Opsumit EPAR". European Medicines Agency (EMA). 27 September 2011. Retrieved 6 August 2024.
  5. ^ 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.
  6. ^ 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)
  7. ^ "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.
  8. ^ "Macitentan: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 19 June 2021.