Bosentan

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Bosentan
Bosentan.svg
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 names Tracleer
AHFS/Drugs.com monograph
MedlinePlus a605001
Pregnancy cat. X
Legal status Prescription only
Routes Oral
Pharmacokinetic data
Bioavailability 50%
Protein binding >98%
Metabolism Hepatic
Half-life 5 hours
Identifiers
CAS number 147536-97-8 YesY
ATC code C02KX01
PubChem CID 104865
DrugBank DB00559
ChemSpider 94651 YesY
UNII XUL93R30K2 YesY
KEGG D01227 N
ChEBI CHEBI:51450 YesY
ChEMBL CHEMBL957 YesY
Chemical data
Formula C27H29N5O6S 
Mol. mass 551.614 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 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.[1]

Clinical uses[edit]

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.[citation needed]

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.[2]

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.[3]

Hormone-based contraception is not possible in women taking Bosentan, due to a pharmacokinetic interaction.[4] Therefore, other highly reliable forms of contraception should be used instead.

Bosentan is contraindicated in pregnancy because of its teratogenicity (Pregnancy Category X). [5] [6]

See also[edit]

References[edit]

  1. ^ Funke C, Farr M, Werner B, Dittmann S, Uberla K, Piper C, Niehaus K, Horstkotte D (Apr 2010). "Antiviral effect of Bosentan and Valsartan during coxsackievirus B3 infection of human endothelial cells.". Journal of General Virology 91 (8): 1959–1570. doi:10.1099/vir.0.020065-0. PMID 20392896. 
  2. ^ http://www.tracleer.com/pdf/09%20276%2001%2000%200809_Tra%20PI_4%20Pg_081409pdf.pdf
  3. ^ http://www.ionchannels.org/showabstract.php?pmid=15875338
  4. ^ http://www.ionchannels.org/showabstract.php?pmid=15875338
  5. ^ http://www.medicinescomplete.com/mc/bnf/current/PHP1044-bosentan.htm?q=bosentan&t=search&ss=text&p=1#_hit
  6. ^ http://www.nzf.org.nz/nzf_1183.html

External links[edit]