Structure via PubChem · Public domain (PubChem)
ambrisentan
Sign in to saveAlso known as Letairis®, (2S)-2-[(4,6-dimethylpyrimidin-2-yl)oxy]-3-methoxy- 3,3-diphenylpropanoic acid
Ambrisentan, sold under the brand name Letairis among others, is a drug used for the treatment of pulmonary hypertension. It is an endothelin receptor antagonist.
Chemical data
- Formula
- C22H22N2O4
- Molecular weight
- 378.4 g/mol
- IUPAC name
- (2S)-2-(4,6-dimethylpyrimidin-2-yl)oxy-3-methoxy-3,3-diphenylpropanoic acid
- SMILES
- CC1=CC(=NC(=N1)O[C@H](C(=O)O)C(C2=CC=CC=C2)(C3=CC=CC=C3)OC)C
- InChIKey
- OUJTZYPIHDYQMC-LJQANCHMSA-N
- XLogP
- 3.8
- Polar surface area
- 81.5 Ų
- H-bond donors
- 1
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 2007
- Admin. routes
- oral
- Indications
- pulmonary arterial hypertension, idiopathic pulmonary fibrosis, vascular disease, hypertension
via ChEMBL · EBI
Research
582 papers- Ambrisentan.2006
- Ambrisentan.2012
- Ambrisentan.Drugs · 2008
- Ambrisentan.American journal of cardiovascular drugs : drugs, devices, and other interventions · 2011
- Initial Use of Ambrisentan plus Tadalafil in Pulmonary Arterial Hypertension.The New England journal of medicine · 2015
via PubMed
Wikidata facts
- Mass
- 378.158
- Has use
- medication
Show 8 more facts
- chemical formula
- C₂₂H₂₂N₂O₄
- isomeric SMILES
- CC1=CC(=NC(=N1)O[C@H](C(=O)O)C(C2=CC=CC=C2)(C3=CC=CC=C3)OC)C
- canonical SMILES
- CC1=CC(=NC(=N1)OC(C(=O)O)C(C2=CC=CC=C2)(C3=CC=CC=C3)OC)C
- subject has role
- antihypertensive drug
- medical condition treated
- pulmonary hypertension
- Commons category
- Ambrisentan
- defined daily dose
- 7.5
- legal status (medicine)
- boxed warning
Sources (9)
via Wikidata · CC0
~3 min read
Encyclopedic overview
7 sectionsContents
- Medical uses
- Mechanism of action
- Birth defects
- Society and culture
- Brand names
- Publications
- References
Ambrisentan, sold under the brand name Letairis among others, is a drug used for the treatment of pulmonary hypertension. It is an endothelin receptor antagonist.
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). Ambrisentan significantly improved exercise capacity (6-minute walk distance) compared with placebo in two double-blind, multicenter trials (ARIES-1 and ARIES-2). 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.
Excerpted from Wikipedia’s “ambrisentan” article, available under the CC BY-SA 4.0 licence.