Ambrisentan

Ambrisentan
Clinical data
Trade namesLetairis, Volibris, Pulmonext
AHFS/Drugs.comMonograph
MedlinePlusa612023
License data
Pregnancy
category
  • AU: X (High risk)
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding99%
Elimination half-life15 hours (terminal)
Identifiers
  • (2S)-2-[(4,6-dimethylpyrimidin-2-yl)oxy]-3-methoxy-3,3-diphenylpropanoic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.184.855 Edit this at Wikidata
Chemical and physical data
FormulaC22H22N2O4
Molar mass378.428 g·mol−1
3D model (JSmol)
  • O=C(O)[C@@H](Oc1nc(cc(n1)C)C)C(OC)(c2ccccc2)c3ccccc3
  • InChI=1S/C22H22N2O4/c1-15-14-16(2)24-21(23-15)28-19(20(25)26)22(27-3,17-10-6-4-7-11-17)18-12-8-5-9-13-18/h4-14,19H,1-3H3,(H,25,26)/t19-/m1/s1 checkY
  • Key:OUJTZYPIHDYQMC-LJQANCHMSA-N checkY
  (verify)

Ambrisentan, sold under the brand name Letairis among others, is a drug used for the treatment of pulmonary hypertension.[3][5] It is an endothelin receptor antagonist.[3]

The peptide endothelin constricts muscles in blood vessels, increasing blood pressure. Ambrisentan, which relaxes those muscles, is an endothelin receptor antagonist, and is selective for the type A endothelin receptor (ETA).[6] Ambrisentan significantly improved exercise capacity (6-minute walk distance) compared with placebo in two double-blind, multicenter trials (ARIES-1 and ARIES-2).[7] Like all endothelin receptor antagonists, Ambrisentan is contraindicated in pregnant women as well as those who are trying to become pregnant, due to the potential for teratogenic effects on the fetus.[8]

Ambrisentan was approved by the US Food and Drug Administration (FDA) and the European Medicines Agency (EMA), and designated an orphan drug, for the treatment of pulmonary hypertension.[9][4][10][11]

  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 generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
  3. ^ a b c "Letairis- ambrisentan tablet, film coated". DailyMed. 4 September 2019. Retrieved 18 April 2020.
  4. ^ a b "Volibris EPAR". European Medicines Agency (EMA). 17 September 2018. Retrieved 18 April 2020.
  5. ^ "Ambrisentan Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. 7 January 2019. Retrieved 18 April 2020.
  6. ^ Vatter H, Seifert V (2006). "Ambrisentan, a non-peptide endothelin receptor antagonist". Cardiovascular Drug Reviews. 24 (1): 63–76. doi:10.1111/j.1527-3466.2006.00063.x. PMID 16939634.
  7. ^ Frampton JE (August 2011). "Ambrisentan". American Journal of Cardiovascular Drugs. 11 (4): 215–26. doi:10.2165/11207340-000000000-00000. PMID 21623643. S2CID 262016778.
  8. ^ Galiè N, Olschewski H, Oudiz RJ, Torres F, Frost A, Ghofrani HA, et al. (June 2008). "Ambrisentan for the treatment of pulmonary arterial hypertension: results of the ambrisentan in pulmonary arterial hypertension, randomized, double-blind, placebo-controlled, multicenter, efficacy (ARIES) study 1 and 2". Circulation. 117 (23): 3010–9. doi:10.1161/CIRCULATIONAHA.107.742510. PMID 18506008.
  9. ^ "Drug Approval Package: Letairis (ambrisentan) NDA #022081". U.S. Food and Drug Administration (FDA). 24 December 1999. Retrieved 18 April 2020.
  10. ^ "Ambrisentan Orphan Drug Designation and Approval". U.S. Food and Drug Administration (FDA). Retrieved 18 April 2020.
  11. ^ Pollack A (16 June 2007). "Gilead's Drug Is Approved to Treat a Rare Disease". The New York Times. Archived from the original on 24 May 2013. Retrieved 16 June 2007.