Bosentan
Highest phase reached
Approved
Drug type
Small molecule
First approval year
2001
- First approval year
- 2001
- Listing at source
- Listed
- Highest phase reached
- Approved
- Drug type
- Small molecule
- Drug name
- Bosentan
- Molecular weight
- 551.63
- Structure (SMILES)
- COc1ccccc1Oc1c(NS(=O)(=O)c2ccc(C(C)(C)C)cc2)nc(-c2ncccn2)nc1OCCO
- stayveer
- Stayveer
- tracleer
- Tracleer
- anhydrous bosentan
- Anhydrous bosentan
- bosentan
- Bosentan
- Bosentan (as monohydrate)
- bosentan [INN]
- BOSENTAN [MI]
- Bosentan [WHO-DD]
- bosentan 125 mg
- bosentan 62 5 mg
- bosentan ambrisentan
- bosentan and dapagliflozin
- bosentan anhydrous
- Bosentan anhydrous
- bosentan as monohydrate
- bosentan hydrate
- Bosentan hydrate
- bosentan inn
- bosentan mi
- bosentan monohydrate
- Bosentan monohydrate
- bosentan tablets
- bosentan tracleer
- bosentan who dd
- oral bosentan 62 5 mg
And 10 more, listed on the interactive page.
- ATC classification codes
- C02KX01
Sources for recorded values
- CAS registry numbers
- 147536-97-8
- ChEMBL ID
- CHEMBL957
- InChIKey
- GJPICJJJRGTNOD-UHFFFAOYSA-N
- PubChem compound IDs
- 104865
- FDA ingredient codes (UNII)
- XUL93R30K2
- 75207
- 498193
- 1468845
- Applicant
- ACTELION
- Approval date
- 20 Nov 2001
- Application number
- NDA021290
- Status
- Authorised
- Status date
- 14 May 2002
- Authorisation date
- 14 May 2002
- Approved indications
- Treatment of pulmonary arterial hypertension (PAH) to improve exercise capacity and symptoms in patients with WHO functional class III.Efficacy has been shown in: Primary (idiopathic and familial) PAH; PAH secondary to scleroderma without significant interstitial pulmonary disease; PAH associated with congenital systemic-to-pulmonary shunts and Eisenmenger's physiology. Some improvements have also been shown in patients with PAH WHO functional class II. Tracleer is also indicated to reduce the number of new digital ulcers in patients with systemic sclerosis and ongoing digital ulcer disease.
- Product number
- EMEA/H/C/000401
- Priority medicines scheme
- No
- Generic
- No
- Biosimilar
- No
- Generic medicines
- 0
- Biosimilar medicines
- 0
- Advanced therapy
- No
- Conditional approval
- No
- Additional monitoring
- No
- Accelerated assessment
- No
- Exceptional circumstances
- No
Therapeutic areas
- Hypertension, Pulmonary
- Scleroderma, Systemic
European medicines record
- Patents
- 2
- Designations
- 1
- Earliest recorded loss of exclusivity
- 28 Dec 2027
- First in class
- No
- Fast track
- No
- Breakthrough designation
- No
- Orphan designation
- No
- Priority review
- No
- Orphan exclusivity
- No
- Accelerated approval
- No
- Availability
- Prescription only
- Boxed warning
- Yes
- United States (FDA)
- Approved
- European Union (EMA)
- Authorised
- Pharmacology name
- bosentan
- Type
- Synthetic organic
- Drug name stem
- -entan
- Approval recorded by Guide to Pharmacology
- Yes
Administration routes
- Oral
- Action
- Antagonist
- Action type
- Antagonist
- Target
- ETB receptor
- Gene symbol
- EDNRB
- Protein identifier
- P24530
- Median affinity
- 7.1
- Affinity units
- pKi
- Primary target
- Yes
- Mechanism
- Endothelin receptor, ET-A/ET-B antagonist
- Action type
- Antagonist
- Target
- Endothelin receptor, ET-A/ET-B
- Protein identifier
- P24530
- Mechanism
- Endothelin receptor, ET-A/ET-B antagonist
- Action type
- Antagonist
- Target
- Endothelin receptor, ET-A/ET-B
- Protein identifier
- P25101
Open Targets mechanisms
- Mechanism
- Endothelin receptor, ET-A/ET-B antagonist
- Action type
- Antagonist
- Target
- Endothelin receptor, ET-A/ET-B
- Action type
- Antagonist
- Gene symbol
- EDNRB
- Protein identifier
- P24530
- Organism
- Homo sapiens
- Target development level
- Clinical
- Action type
- Antagonist
- Gene symbol
- EDNRA
- Protein identifier
- P25101
- Organism
- Homo sapiens
- Target development level
- Clinical
- Condition
- Pulmonary Disease, Chronic Obstructive
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000341
- Subject identifier
- D029424
- Condition
- Heart Failure
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000373
- Subject identifier
- D006333
- Condition
- Diabetes Mellitus
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000400
- Subject identifier
- D003920
- Condition
- Hypertension
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000537
- Subject identifier
- D006973
- Condition
- Neoplasms
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000616
- Subject identifier
- D009369
- Condition
- Scleroderma, Systemic
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000717
- Subject identifier
- D012595
- Condition
- Melanoma
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000756
- Subject identifier
- D008545
- Condition
- Idiopathic Pulmonary Fibrosis
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000768
- Subject identifier
- D054990
- Condition
- Pulmonary Arterial Hypertension
- Highest recorded phase
- 4
- Condition identifier
- EFO:0001361
- Subject identifier
- D000081029
- Condition
- Hypertension, Pulmonary
- Highest recorded phase
- 4
- Condition identifier
- EFO:0001361
- Subject identifier
- D006976
- Condition
- Liver Cirrhosis
- Highest recorded phase
- 2
- Condition identifier
- EFO:0001422
- Subject identifier
- D008103
- Condition
- Pancreatic Neoplasms
- Highest recorded phase
- 1
- Condition identifier
- EFO:0002618
- Subject identifier
- D010190
- Condition
- Sleep Apnea Syndromes
- Highest recorded phase
- 0.5
- Condition identifier
- EFO:0003877
- Subject identifier
- D012891
- Condition
- Heart Defects, Congenital
- Highest recorded phase
- 4
- Condition identifier
- EFO:0005207
- Subject identifier
- D006330
- Condition
- Hernias, Diaphragmatic, Congenital
- Highest recorded phase
- 2
- Condition identifier
- EFO:0005207
- Subject identifier
- D065630
- Condition
- Mitral Valve Stenosis
- Highest recorded phase
- 1
- Condition identifier
- EFO:0007372
- Subject identifier
- D008946
- Condition
- Eisenmenger Complex
- Highest recorded phase
- 3
- Condition identifier
- EFO:0009200
- Subject identifier
- D004541
- Condition
- Optic Neuropathy, Ischemic
- Highest recorded phase
- 3
- Condition identifier
- EFO:1000809
- Subject identifier
- D018917
- Condition
- Persistent Fetal Circulation Syndrome
- Highest recorded phase
- 3
- Condition identifier
- EFO:1001103
- Subject identifier
- D010547
- Condition
- Fever
- Highest recorded phase
- 1
- Condition identifier
- HP:0001945
- Subject identifier
- D005334
- Condition
- Hypoplastic Left Heart Syndrome
- Highest recorded phase
- 2
- Condition identifier
- MONDO:0004933
- Subject identifier
- D018636
- Condition
- Asthma
- Highest recorded phase
- 2
- Condition identifier
- MONDO:0004979
- Subject identifier
- D001249
- Condition
- Glaucoma
- Highest recorded phase
- 1
- Condition identifier
- MONDO:0005041
- Subject identifier
- D005901
- Condition
- Diabetes Mellitus, Type 2
- Highest recorded phase
- 3
- Condition identifier
- MONDO:0005148
- Subject identifier
- D003924
- Condition
- Hypertension, Pulmonary
- Highest recorded phase
- 4
- Condition identifier
- MONDO:0005149
- Subject identifier
- D006976
And 4 more, listed on the interactive page.
- Condition identifier
- EFO_0000341
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000373
- Condition identifier
- EFO_0000400
- Highest recorded phase
- 1
- Condition identifier
- EFO_0000537
- Condition identifier
- EFO_0000616
- Highest recorded phase
- 1
- Condition identifier
- EFO_0000717
- Condition identifier
- EFO_0000756
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000768
- Highest recorded phase
- 3
- Condition identifier
- EFO_0001361
- Condition identifier
- EFO_0001422
- Highest recorded phase
- 2
- Condition identifier
- EFO_0003877
- Condition identifier
- EFO_0005207
- Condition identifier
- EFO_0007372
- Condition identifier
- EFO_0009200
- Highest recorded phase
- 3
- Condition identifier
- EFO_0009878
- Condition identifier
- EFO_0022954
- Highest recorded phase
- 3
- Condition identifier
- EFO_1000809
- Highest recorded phase
- 3
- Condition identifier
- EFO_1001103
- Highest recorded phase
- 3
- Condition identifier
- EFO_1001211
- Condition identifier
- HP_0000618
- Highest recorded phase
- 3
- Condition identifier
- HP_0000822
- Highest recorded phase
- 2
- Condition identifier
- HP_0000855
- Highest recorded phase
- 2
- Condition identifier
- HP_0001945
- Condition identifier
- HP_0002243
- Highest recorded phase
- 2
- Condition identifier
- HP_0005310
- Highest recorded phase
- 2
And 33 more, listed on the interactive page.
- Warning
- Black Box Warning
- Effect
- hepatotoxicity
- Warning
- Black Box Warning
- Effect
- teratogenicity
- Warning
- Black Box Warning
- Effect
- hepatotoxicity
- Country
- United States
- Warning
- Black Box Warning
- Effect
- teratogenicity
- Country
- United States
- Event
- alanine aminotransferase increased
- Reports
- 963
- Reporting signal score
- 1,246.41
- Event
- aspartate aminotransferase increased
- Reports
- 983
- Reporting signal score
- 1,394.82
- Event
- atrial fibrillation
- Reports
- 481
- Reporting signal score
- 321.086
- Event
- blood alkaline phosphatase increased
- Reports
- 550
- Reporting signal score
- 891.223
- Event
- blood bilirubin increased
- Reports
- 369
- Reporting signal score
- 467.601
- Event
- cardiac disorder
- Reports
- 307
- Reporting signal score
- 251.925
- Event
- cardiac failure congestive
- Reports
- 479
- Reporting signal score
- 395.31
- Event
- cardiac operation
- Reports
- 195
- Reporting signal score
- 498.232
- Event
- cardiac pacemaker insertion
- Reports
- 198
- Reporting signal score
- 499.598
- Event
- catheterisation cardiac
- Reports
- 166
- Reporting signal score
- 413.876
- Event
- chest pain
- Reports
- 671
- Reporting signal score
- 337.791
- Event
- chronic obstructive pulmonary disease
- Reports
- 318
- Reporting signal score
- 345.143
- Event
- concomitant disease aggravated
- Reports
- 134
- Reporting signal score
- 258.939
- Event
- condition aggravated
- Reports
- 873
- Reporting signal score
- 357.148
- Event
- cough
- Reports
- 774
- Reporting signal score
- 327.28
- Event
- dyspnoea
- Reports
- 2,887
- Reporting signal score
- 2,420.27
- Event
- dyspnoea exertional
- Reports
- 353
- Reporting signal score
- 430.651
- Event
- fall
- Reports
- 944
- Reporting signal score
- 339.232
- Event
- fluid overload
- Reports
- 234
- Reporting signal score
- 389.35
- Event
- fluid retention
- Reports
- 722
- Reporting signal score
- 1,287.79
- Event
- influenza
- Reports
- 399
- Reporting signal score
- 269.361
- Event
- liver function test abnormal
- Reports
- 657
- Reporting signal score
- 1,030.7
- Event
- lung transplant
- Reports
- 254
- Reporting signal score
- 741.853
- Event
- oedema
- Reports
- 461
- Reporting signal score
- 478.481
- Event
- oedema peripheral
- Reports
- 683
- Reporting signal score
- 444.821
And 9 more, listed on the interactive page.
- NCT00071461
- NCT00391443
- NCT00631475
- NCT00077584
- NCT00226889
- NCT00318175
- NCT00377455
- NCT01241383
- NCT01395732
- NCT02480335
- NCT00082186
- NCT00260819
- NCT00303459
- NCT00313222
- NCT00317486
- NCT00319020
- NCT00319267
- NCT00323297
- NCT00433329
- NCT00595049
- NCT00820352
- NCT00825266
- NCT01100736
- NCT01223352
- NCT01270750
And 38 more, listed on the interactive page.
- Hydrogen bond acceptors
- 10
- Hydrogen bond donors
- 2
- Polar surface area
- 145.65
- Calculated partition coefficient (ALogP)
- 4.2
- Calculated partition coefficient (XLogP)
- 3.8
- Prodrug
- No
- Chirality
- Achiral
- Inorganic
- No
- Rule-of-five violations
- 1
- Rotatable bonds
- 10
- Heavy atoms
- 39
- Molecular formula
- C27H29N5O6S
- Monoisotopic mass
- 551.18385484
- Natural product
- Yes
- Recorded assays
- 1,427
- Active assays
- 96
- Confirmatory
- Other
- Screening
- Summary
- Antihypertensive Agents
- Endothelin Receptor Antagonists
Distribution coefficient (LogD)
- Median
- 1.8
- Mean
- 1.8
- Minimum
- 1.2
- Maximum
- 2.4
- Unit
- unitless
- Assays
- 2
- Standard deviation
- 0.848528
- Summary method
- median
- Censored results excluded
- 0
- Other units excluded
- 0
- Unknown units excluded
- 0
Measurement types
- LogD
Oral bioavailability
- Median
- 40
- Mean
- 40
- Minimum
- 30
- Maximum
- 50
- Unit
- %
- Assays
- 2
- Standard deviation
- 14.1421
- Summary method
- median
- Censored results excluded
- 0
- Other units excluded
- 0
- Unknown units excluded
- 0
Measurement types
- F
Related records
Trials (102)
- A Clinical Trial to Evaluate MK-4208/Embibatinib in Healthy Adult Participants (MK-4208-001/Embibatinib-1014)
- A Study in Healthy Men to Test How Bosentan Influences the Amount of Nerandomilast in the Blood
- A Study in Healthy Men to Test How Bosentan Influences the Amount of Zongertinib in the Blood
- A Study in Healthy Men to Test Whether Bosentan Influences the Amount of BI 425809 in the Blood
- A Study of Patients Having Pulmonary Hypertension Associated With Sickle Cell Disease and Completing an ASSET Study
- A Study to Evaluate the Use of Bosentan in Patients With Exercise Induced Pulmonary Arterial Hypertension Associated With Connective Tissue Disease
- Assess the Efficacy and Safety of Sildenafil When Added to Bosentan in the Treatment of Pulmonary Arterial Hypertension
- Bioequivalence Study of Bosentan 125 mg Tablets Immediate Release (IR) Versus Tracleer® 125 mg Tablets IR In Healthy Subjects
- Bioequivalence Study to Compare Bosentan 32 mg Dispersible Tablets Versus Tracleer® 32 mg Tablets
- Bosentan and Pulmonary Endothelial Function
- Bosentan Effects in Inoperable Forms of Chronic Thromboembolic Pulmonary Hypertension
- Bosentan for Mild Pulmonary Vascular Disease in Asd Patients.
- Bosentan for Poorly Controlled Asthma
- Bosentan for Severe Mitral Valve Dysfunction
- Bosentan for Treatment of Hepatopulmonary Syndrome in Patients With Liver Cirrhosis
- Bosentan Improves Clinical Outcome of Adults With Congenital Heart Disease or Mitral Valve Lesions Who Undergo CArdiac Surgery
- Bosentan in Children With Pulmonary Arterial Hypertension
- Bosentan in Children With Pulmonary Arterial Hypertension Extension Study
- Bosentan in Digital Ulcers
- Bosentan In Exercise Induced Pulmonary Arterial Hypertension in CongenitaL Heart diseasE
Approved for (7)
- Congenital heart disease
- Heritable pulmonary arterial hypertension
- Hypertensive disorder
- Obsolete idiopathic and/or familial pulmonary arterial hypertension
- Pulmonary arterial hypertension
- Pulmonary hypertension
- Systemic sclerosis
In development for (31)
- Anterior ischemic optic neuropathy Phase 3
- Asthma Phase 2
- Atrial septal defect 1 Phase 3
- Chronic obstructive pulmonary disease Phase 2
- Cirrhosis of liver Phase 2
- Congestive heart failure Phase 1
- Diabetes mellitus Phase 1
- Diabetic kidney disease Phase 3
- Eisenmenger syndrome Phase 3
- Exocrine pancreatic carcinoma Phase 1
- Familial multiple nevi flammei Phase 2
- Glaucoma Phase 1
- Hermansky-Pudlak syndrome Phase 2
- Hypoplastic left heart syndrome Phase 2
- Idiopathic pulmonary fibrosis Phase 3
- Interstitial lung disease Phase 2
- Malignant pancreatic neoplasm Phase 1
- Melanoma Phase 2
- Mitral valve stenosis Phase 1
- Neoplasm Phase 1
Other linked conditions (2)
- Intermittent vascular claudication
- Thromboangiitis obliterans