Bosentan

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Bosentan
Systematic (IUPAC) name
4-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-(pyrimidin-2-yl)pyrimidin-4-yl]benzene-1-sulfonamide
Clinical data
Trade namesTracleer
AHFS/Drugs.commonograph
MedlinePlusa605001
Pregnancy cat.X
Legal status Prescription only
RoutesOral
Pharmacokinetic data
Bioavailability50%
Protein binding>98%
MetabolismHepatic
Half-life5 hours
Identifiers
CAS number147536-97-8 YesY
ATC codeC02KX01
PubChemCID 104865
DrugBankDB00559
ChemSpider94651 YesY
UNIIXUL93R30K2 YesY
KEGGD01227 N
ChEBICHEBI:51450 YesY
ChEMBLCHEMBL957 YesY
Chemical data
FormulaC27H29N5O6S 
Mol. mass551.614 g/mol
 N (what is this?)  (verify)
 
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Bosentan
Systematic (IUPAC) name
4-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-(pyrimidin-2-yl)pyrimidin-4-yl]benzene-1-sulfonamide
Clinical data
Trade namesTracleer
AHFS/Drugs.commonograph
MedlinePlusa605001
Pregnancy cat.X
Legal status Prescription only
RoutesOral
Pharmacokinetic data
Bioavailability50%
Protein binding>98%
MetabolismHepatic
Half-life5 hours
Identifiers
CAS number147536-97-8 YesY
ATC codeC02KX01
PubChemCID 104865
DrugBankDB00559
ChemSpider94651 YesY
UNIIXUL93R30K2 YesY
KEGGD01227 N
ChEBICHEBI:51450 YesY
ChEMBLCHEMBL957 YesY
Chemical data
FormulaC27H29N5O6S 
Mol. mass551.614 g/mol
 N (what is this?)  (verify)

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.

Mechanism of action[edit]

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 pulmonary vasoconstriction. By blocking this interaction, bosentan decreases pulmonary vascular resistance. Bosentan has a slightly higher affinity for ET-A than ET-B.

Clinical uses[edit]

Bosentan is indicated mainly for the treatment of pulmonary hypertension. In 2007, bosentan was approved in the European Union also 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 WHO Class II-IV symptoms, to improve exercise capacity and decrease the rate of clinical worsening.[1]

Warnings[edit]

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

Bosentan use requires hematocrit monitoring due to potential onset of anemia. [2]

Hormone-based contraception is not possible in women taking Bosentan, due to a pharmacokinetic interaction. [3] Therefore, other highly reliable forms of contraception should be used instead.

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

See also[edit]

References[edit]

External links[edit]