Tracleer

Bosentan

Clinical data
Trade names	Tracleer
AHFS/Drugs.com	Monograph
MedlinePlus	a605001
Pregnancy category	X
Routes of administration	Oral
ATC code	C02KX01 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	50%
Protein binding	>98%
Metabolism	Hepatic
Biological half-life	5 hours
Identifiers
IUPAC name 4-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-(pyrimidin-2-yl)pyrimidin-4-yl]benzene-1-sulfonamide
CAS Number	147536-97-8 Y
PubChem CID	104865
IUPHAR/BPS	3494
DrugBank	DB00559 Y
ChemSpider	94651 Y
UNII	XUL93R30K2
KEGG	D01227 N
ChEBI	CHEBI:51450 Y
ChEMBL	CHEMBL957 Y
ECHA InfoCard	100.171.206
Chemical and physical data
Formula	C27H29N5O6S
Molar mass	551.614 g/mol
3D model (Jmol)	Interactive image
SMILES CC(C)(C)c1ccc(cc1)S(=O)(=O)Nc2c(c(nc(n2)c3ncccn3)OCCO)Oc4ccccc4OC
InChI InChI=1S/C27H29N5O6S/c1-27(2,3)18-10-12-19(13-11-18)39(34,35)32-23-22(38-21-9-6-5-8-20(21)36-4)26(37-17-16-33)31-25(30-23)24-28-14-7-15-29-24/h5-15,33H,16-17H2,1-4H3,(H,30,31,32) Y Key:GJPICJJJRGTNOD-UHFFFAOYSA-N Y
NY (what is this?)

Bosentan is a dual endothelin receptor antagonist used in the treatment of pulmonary artery hypertension (PAH). It is licensed in the United States, the European Union and other countries by Actelion Pharmaceuticals for the management of PAH under the trade name Tracleer.

Bosentan is indicated mainly for the treatment of pulmonary hypertension. In 2007, Bosentan was also approved in the European Union for reducing the number of new digital ulcers in patients with systemic sclerosis and ongoing digital ulcer disease.

In the United States, Bosentan is indicated for the treatment of pulmonary arterial hypertension (WHO Group I) in patients with NYHA Class II-IV symptoms, to improve exercise capacity and decrease the rate of clinical worsening.

Due to potential hepatotoxicity, the FDA requires monthly monitoring of liver function tests while taking Bosentan.

Bosentan use requires monitoring due to potential onset of anemia.

Hormone-based contraception is not possible in women taking Bosentan, due to a pharmacokinetic interaction. Therefore, other highly reliable forms of contraception should be used instead.

Bosentan is contraindicated in pregnancy because of its teratogenicity (Pregnancy Category X).

Bosentan is a competitive antagonist of endothelin-1 at the endothelin-A (ET-A) and endothelin-B (ET-B) receptors. Under normal conditions, endothelin-1 binding of ET-A or ET-B receptors causes constriction of the pulmonary blood vessels. By blocking this interaction, bosentan decreases pulmonary vascular resistance. Bosentan has a slightly higher affinity for ET-A than ET-B.