Compound Detail
CHEMBL957
BOSENTAN 💊 Approved Drug
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💊 Approved Drug
COc1ccccc1Oc1c(NS(=O)(=O)c2ccc(C(C)(C)C)cc2)nc(-c2ncccn2)nc1OCCO
Basic Information
| ChEMBL ID | CHEMBL957 |
| Name | BOSENTAN |
| Phase | Approved |
| Structure Type | MOL |
| InChI Key | GJPICJJJRGTNOD-UHFFFAOYSA-N |
| Therapeutic | ✓ Yes |
14
Targets
54
Activities
4
Assay Types
22
PK Parameters
20
Publications
12
Known Names
20
Indications
1
Mechanisms
Molecular Properties
551.6
MW (Da)
4.20
ALogP
10
HBA
2
HBD
145.7
PSA (Ų)
0.29
QED
1
Ro5 Violations
10
Rot. Bonds
Drug Information
| Molecule Type | Small molecule |
| First Approval | 2001 |
| Availability | Prescription |
| Chirality | Achiral |
Mechanism of Action
| Mechanism | Action Type | Target | Direct | Efficacy |
|---|---|---|---|---|
| Endothelin receptor, ET-A/ET-B antagonist | ANTAGONIST | Endothelin receptor, ET-A/ET-B | ✓ | ✓ |
Indications
Familial Primary Pulmonary Hypertension Heart Defects, Congenital Hypertension Hypertension, Pulmonary Hypertension, Pulmonary Pulmonary Arterial Hypertension Scleroderma, Systemic Diabetes Mellitus, Type 2 Eisenmenger Complex Heart Septal Defects, Atrial Idiopathic Pulmonary Fibrosis Optic Neuropathy, Ischemic Persistent Fetal Circulation Syndrome Ulcer Asthma Hermanski-Pudlak Syndrome Hernias, Diaphragmatic, Congenital Hypoplastic Left Heart Syndrome Liver Cirrhosis Melanoma
ATC Classification
C02KX01
bosentan
Level 1: CARDIOVASCULAR SYSTEM
Level 2: ANTIHYPERTENSIVES
Drug Warnings
Black Box Warning
teratogenicity
Black Box Warning
hepatotoxicity
Activity Summary
IC50 36 meas. best 8.33
Ki 10 meas. best 8.44
EC50 4 meas. best 6.28
Kd 4 meas. best 7.4
Target Activity Profile
| Target | Type | Best pChEMBL | Mean pChEMBL | Best (nM) | # Data |
|---|---|---|---|---|---|
| Endothelin-1 receptor CHEMBL252 | Ki | 8.44 | 8.23 | 3.7 | 4 |
| Endothelin-1 receptor CHEMBL252 | IC50 | 8.33 | 7.4954 | 4.7 | 13 |
| Endothelin-1 receptor CHEMBL4566 | IC50 | 8.33 | 8.33 | 4.7 | 1 |
| Endothelin-1 receptor CHEMBL4566 | Ki | 8.19 | 8.19 | 6.5 | 1 |
| Endothelin-1 receptor CHEMBL4130 | IC50 | 8.12 | 8.12 | 7.5 | 1 |
| Endothelin-1 receptor CHEMBL4566 | Kd | 7.4 | 7.28 | 39.8 | 3 |
| Endothelin receptor type B CHEMBL1785 | Ki | 7.1 | 6.6 | 80.0 | 4 |
| Endothelin receptor type B CHEMBL1785 | IC50 | 7.02 | 6.6638 | 95.0 | 8 |
| Endothelin receptor type B CHEMBL4631 | IC50 | 7.02 | 7.02 | 95.0 | 1 |
| Unchecked CHEMBL612545 | EC50 | 6.28 | 6.28 | 530.0 | 1 |
| Endothelin receptor type B CHEMBL4631 | Kd | 5.8 | 5.8 | 1584.9 | 1 |
| Nuclear receptor subfamily 1 group I member 2 CHEMBL3401 | EC50 | 5.05 | 4.9333 | 8900.0 | 3 |
| Bile salt export pump CHEMBL2073674 | Ki | 4.92 | 4.92 | 12000.0 | 1 |
| ATP-binding cassette sub-family C member 4 CHEMBL1743128 | IC50 | 4.66 | 4.66 | 22000.0 | 1 |
| Bile salt export pump CHEMBL6020 | IC50 | 4.66 | 4.565 | 22000.0 | 4 |
| Bile salt export pump CHEMBL2073674 | IC50 | 4.51 | 4.51 | 30600.0 | 1 |
| ATP-binding cassette sub-family C member 3 CHEMBL5918 | IC50 | 4.38 | 4.38 | 42000.0 | 1 |
| SK-MEL-28 CHEMBL614919 | IC50 | 4.27 | 4.27 | 53650.0 | 1 |
| Deoxyhypusine synthase CHEMBL4415 | IC50 | 4.22 | 4.22 | 60830.0 | 1 |
| A-375 CHEMBL613859 | IC50 | 4.17 | 4.17 | 67360.0 | 1 |
Pharmacokinetic Data
| Parameter | Value | Units | Species |
|---|---|---|---|
| AUC | 8914.34 | ng.hr.mL-1 | Homo sapiens |
| CL | 55.0 | mL.min-1.kg-1 | Rattus norvegicus |
| CL | 1.9 | mL.min-1.kg-1 | Canis lupus familiaris |
| CL | 3.7 | mL.min-1.kg-1 | Homo sapiens |
| CL | 2.1 | mL.min-1.kg-1 | Homo sapiens |
| CL | 4.79 | uL.min-1.(10^6cells)-1 | Homo sapiens |
| CL | 15.14 | mL.min-1.g-1 | Homo sapiens |
| CL | 16.0 | mL.min-1.kg-1 | Homo sapiens |
| CL | 15.9 | mL.min-1.kg-1 | Rattus norvegicus |
| CL | 33.1 | mL.min-1.kg-1 | Macaca fascicularis |
| CL | 2.2 | mL.min-1.kg-1 | Homo sapiens |
| Cmax | 7433.0 | nM | Homo sapiens |
| F | 30.0 | % | Rattus norvegicus |
| F | 50.0 | % | Homo sapiens |
| Fu | 0.037 | - | Homo sapiens |
| Fu | 0.000121 | - | Rattus norvegicus |
| Fu | 0.000422 | - | Macaca fascicularis |
| Fu | 0.000285 | - | Homo sapiens |
| MRT | 2.3 | hr | Homo sapiens |
| T1/2 | 4.0 | hr | Rattus norvegicus |
| T1/2 | 4.1 | hr | Homo sapiens |
| T1/2 | 0.01667 | hr | Homo sapiens |
Activity Data Samples
Top measurements by pChEMBL value
Literature References
Data from ChEMBL 36 via Core Engine