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bosentan

Trade name: tracleer

Small moleculeapprovedOrphan Drug FDA

Approved

Nov 20, 2001

Bosentan is a dual endothelin receptor antagonist important 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 used to treat pulmonary hypertension by blocking the action of endothelin molecules that would otherwise promote narrowing of the blood vessels and lead to high blood pressure. Bosentan competitively antagonizes the binding of 125I-labeled ET-1 to human vascular smooth muscle cells (predominantly ETA receptors) with an inhibition constant (Ki ) of 4.7 nM and to human placenta membranes (predominantly ETB receptors) with a Ki of 95 nM. Furthermore, bosentan is specific for endothelin receptors and does not interfere with the binding of a variety of peptides, neurotransmitters, growth factors, or eicosanoids to their receptors. — NCATS

Clinical trial activity

96 trials · 82 clinical orgs · 19 marketing orgs

Phase 1
20
Phase 2
45
Phase 3
30
Phase 4
19

Earliest trial started Jun 1, 2001 (NCT00223717)

Timeline

2000s

  1. Oct 6, 2000

    Orphan Drug Designation

  2. Jan 1, 2001

    Earliest Phase 1 Sponsor(trial)

  3. Nov 20, 2001

    Actelion — Earliest FDA Approval

  4. Nov 20, 2001

    Actelion — Marketing Organization

  5. Nov 20, 2001

    Actelion — NDA Organization

  6. Jan 1, 2003

    Actelion — Earliest Phase 2 Sponsor(trial)

  7. Jan 1, 2003

    Actelion — Earliest Phase 3 Sponsor(trial)

2010s

  1. Sep 5, 2017

    Johnson and Johnson — NDA Secondary Org

  2. Apr 26, 2019

    Endo Pharmaceuticals — Marketing Organization

  3. Apr 26, 2019

    Alvogen — Marketing Organization

  4. Apr 26, 2019

    Amneal Pharmaceuticals — Marketing Organization

  5. Apr 26, 2019

    Natco Pharma — Marketing Organization

  6. Apr 26, 2019

    Par Pharmaceuticals — Marketing Organization

  7. Apr 26, 2019

    Sun Pharmaceuticals — Marketing Organization

  8. Apr 26, 2019

    Watson Pharmaceuticals — Marketing Organization

  9. Apr 26, 2019

    West-Ward Pharmaceutical — Marketing Organization

  10. Apr 26, 2019

    Zydus Discovery DMCC — Marketing Organization

  11. Apr 26, 2019

    Hikma — Marketing Organization

  12. Apr 26, 2019

    Bristol-Myers Squibb — Marketing Organization

  13. Apr 26, 2019

    Allergan PLC (2015) — Marketing Organization

  14. Apr 26, 2019

    PH HEALTH — Marketing Organization

2020s

  1. Jan 3, 2020

    Chartwell Pharmaceuticals — Marketing Organization

  2. Jan 3, 2020

    Cipla — Marketing Organization

  3. Jan 15, 2020

    Mylan — Marketing Organization

  4. Jan 23, 2020

    Alembic — Marketing Organization

Indications

Approved for

Studied for

Mechanism of action

Approval history

  • approvedNov 20, 2001

Chemistry & pharmacology

Loading structure…

SMILES

COC1=C(OC2=C(OCCO)N=C(N=C2NS(=O)(=O)C3=CC=C(C=C3)C(C)(C)C)C4=NC=CC=N4)C=CC=C1
Mol. weight
551.614 g/mol
Lipinski Ro5
1 violation(s)
Rule of 3
No
Chirality
Achiral Molecule
Inorganic
No
Polymer
No
Delivery
Oral
Availability
Prescription Only

Oral

Yes

Parenteral

No

Topical

No

Black box warning

Sources

Also known as

  • 4-(1,1-dimethylethyl)-n-(6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-(2,2'-bipyrimidin)-4-yl) benzenesulfornamide
  • 4-(1,1-dimethylethyl)-n-(6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-(2,2'-bipyrimidin)-4-yl) benzenesulfornamide
  • 4-t-butyl-n-(6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl)benzenesulfonamide
  • actelion
  • bosentan
  • bosentan
  • bosentan
  • bosentan
  • bosentan
  • bosentan
  • bosentan
  • bosentan
  • bosentan
  • bosentan
  • bosentán
  • bosentán
  • bosentan anhydrous
  • bosentan anhydrous
  • bosentan hydrate
  • bosentan hydrate
  • bosentan hydrate
  • bosentan hydrate
  • bosentan hydrate
  • bosentan monohydrate
  • bosentan monohydrate
  • bosentan monohydrate
  • bosentanum
  • bosentanum
  • p-tert-butyl-n-(6-(2-hydroxyethoxy)-5-(o-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl)benzenesulfonamide
  • p-tert-butyl-n-(6-(2-hydroxyethoxy)-5-(o-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl)benzenesulfonamide
  • ro 47-0203
  • ro-47-0203
  • ro-470203029
  • ro-470203029
  • ro-47-0203-029
  • ro-47-0203-029
  • stayveer
  • traclear
  • tracleer
  • tracleer
  • tracleer
  • tracleer
  • tracleer
  • tracleer

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT06957002Phase 2Sep 30, 2025Assistance Publique - Hôpitaux de Paris
NCT07081932Phase 1Aug 26, 2025Boehringer Ingelheim
NCT06887062Phase 2Mar 21, 2025University of Edinburgh
NCT06432452Phase 2/Phase 3 (Phase 3)Aug 1, 2024Maastricht University, Radboud University, Utrecht University
NCT06484673Phase 1Apr 21, 2024Humanis Saglık Anonim Sirketi
NCT05723874Phase 1Mar 6, 2023Boehringer Ingelheim
NCT04770155Early Phase 1 (Phase 1)May 27, 2021University of Mississippi
NCT05072106Phase 1Jan 14, 2021PharmaMar
NCT04388124Phase 2Sep 30, 2020Rouen Normandy University
NCT04039464Phase 3Apr 30, 2020Johns Hopkins University
NCT04158635Phase 1Jan 1, 2020City of Hope National Medical Center, National Cancer Institute (NCI)
NCT04068272Phase 1Sep 7, 2019Instituto Universitario de Oftalmobiología Aplicada, Retinset SL
NCT04101370Phase 1May 24, 2018Geropharm
NCT04991207Phase 1Feb 6, 2018Bial
NCT03229694Phase 4Aug 1, 2017Xuzhou Medical University
NCT05146089Early Phase 1 (Phase 1)Dec 20, 2016Mayo Clinic, National Heart, Lung, and Blood Institute (NHLBI), University of Missouri
NCT03053739Phase 4Dec 1, 2016Postgraduate Institute of Medical Education and Research
NCT02667704Phase 1Feb 1, 2016Boehringer Ingelheim
NCT02480335Phase 4Jun 1, 2015Actelion, University of Groningen
NCT02116335N/AJun 1, 2015Augusta University, National Heart, Lung, and Blood Institute (NHLBI)
Showing 20 of 96 trials
Page 1 / 5

Organizations

Research & Development (82)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
ActelionFor profit452752003
Boehringer IngelheimFor profit3312016
National Heart, Lung, and Blood Institute (NHLBI)Government3032006
Radboud UniversityAcademic/Hospital3322010
University of ViennaAcademic/Hospital3222007
People's Liberation Army of ChinaGovernment2222012
University of AmsterdamAcademic/Hospital2122011
University of BolognaAcademic/Hospital2122006
University of California, Los AngelesAcademic/Hospital2222007
University of CopenhagenAcademic/Hospital2222006
University of EdinburghAcademic/Hospital2222009
University of GrenobleAcademic/Hospital2222007
University of ParisAcademic/Hospital2222006
University of SydneyAcademic/Hospital2022006
Aarhus UniversityAcademic/Hospital1012011
Academisch Medisch Centrum - Universiteit van Amsterdam (AMC-UvA)Academic/Hospital1112011
All India Institute of Medical SciencesAcademic/Hospital1112011
Assistance Publique - Hôpitaux de ParisAcademic/Hospital1112025
Augusta UniversityAcademic/Hospital1112015
BialFor profit1112018
82 organizations
Page 1 / 5

Marketing (24)

OrganizationOrg typeRelationshipDate
ActelionFor profitMKTGNov 20, 2001
ActelionFor profitSYNNov 20, 2001
ActelionFor profitNDANov 20, 2001
AlembicFor profitMKTGJan 23, 2020
AlembicFor profitSYNJan 23, 2020
Allergan PLC (2015)For profitMKTGApr 26, 2019
AlvogenFor profitMKTGApr 26, 2019
Amneal PharmaceuticalsFor profitMKTGApr 26, 2019
Bristol-Myers SquibbFor profitMKTGApr 26, 2019
Chartwell PharmaceuticalsFor profitMKTGJan 3, 2020
CiplaFor profitMKTGJan 3, 2020
Endo PharmaceuticalsFor profitMKTGApr 26, 2019
HikmaFor profitMKTGApr 26, 2019
HikmaFor profitSYNApr 26, 2019
Johnson and JohnsonFor profitNDA2Sep 5, 2017
MylanFor profitMKTGJan 15, 2020
Natco PharmaFor profitMKTGApr 26, 2019
PH HEALTHFor profitMKTGApr 26, 2019
Par PharmaceuticalsFor profitMKTGApr 26, 2019
Sun PharmaceuticalsFor profitMKTGApr 26, 2019
Watson PharmaceuticalsFor profitMKTGApr 26, 2019
West-Ward PharmaceuticalFor profitMKTGApr 26, 2019
Zydus Discovery DMCCFor profitMKTGApr 26, 2019
Zydus Discovery DMCCFor profitSYNFeb 13, 2023