BOSENTAN

Search structure
Synonyms:
Status: Approved (2001)
Entry Type: Small molecule
Molecule Category: UKNOWN
ATC: C02KX01
UNII: XUL93R30K2

Structure
InChI Key GJPICJJJRGTNOD-UHFFFAOYSA-N
Smile COc1ccccc1Oc1c(NS(=O)(=O)c2ccc(C(C)(C)C)cc2)nc(-c2ncccn2)nc1OCCO
InChI
InChI=1S/C27H29N5O6S/c1-27(2,3)18-10-12-19(13-11-18)39(34,35)32-23-22(38-21-9-6-5-8-20(21)36-4)26(37-17-16-33)31-25(30-23)24-28-14-7-15-29-24/h5-15,33H,16-17H2,1-4H3,(H,30,31,32)

Physicochemical Descriptors

Property Name Value
Molecular Formula C27H29N5O6S
Molecular Weight 551.63
AlogP 4.2
Hydrogen Bond Acceptor 10.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 10.0
Polar Surface Area 145.65
Molecular species ACID
Aromatic Rings 4.0
Heavy Atoms 39.0

Pharmacology

Action Mechanism of Action Reference
ANTAGONIST Endothelin receptor, ET-A/ET-B antagonist DailyMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Endothelin receptor
- 5-1585 40-72 7-8 23
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group I Nuclear hormone receptor subfamily 1 group I member 2
8900-14100 - - - -
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 22000-38100 - - -
Transporter Primary active transporter ATP-binding cassette ABCC subfamily
- 22000 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Hypertension, Pulmonary 4 D006976 ClinicalTrials
Hypertension 4 D006973 ClinicalTrials
Hypertension, Pulmonary 4 D006976 ClinicalTrials
Diabetes Mellitus, Type 2 3 D003924 ClinicalTrials
Persistent Fetal Circulation Syndrome 3 D010547 ClinicalTrials
Scleroderma, Systemic 3 D012595 ClinicalTrials
Eisenmenger Complex 3 D004541 ClinicalTrials
Heart Septal Defects, Atrial 3 D006344 ClinicalTrials
Idiopathic Pulmonary Fibrosis 3 D054990 ClinicalTrials
Ulcer 3 D014456 ClinicalTrials
Optic Neuropathy, Ischemic 3 D018917 ClinicalTrials
Melanoma 2 D008545 ClinicalTrials
Hypoplastic Left Heart Syndrome 2 D018636 ClinicalTrials
Hernias, Diaphragmatic, Congenital 2 D065630 ClinicalTrials
Liver Cirrhosis 2 D008103 ClinicalTrials
Hepatopulmonary Syndrome 2 D020065 ClinicalTrials
Pulmonary Disease, Chronic Obstructive 2 D029424 ClinicalTrials
Asthma 2 D001249 ClinicalTrials
Pancreatic Neoplasms 1 D010190 ClinicalTrials
Mitral Valve Stenosis 1 D008946 ClinicalTrials
Heart Failure 1 D006333 ClinicalTrials
Glaucoma 1 D005901 ClinicalTrials
Diabetes Mellitus 1 D003920 ClinicalTrials
Fever 1 D005334 ClinicalTrials

Related Entries

Scaffolds

Cross References

Resources Reference
ChEBI 51450
ChEMBL CHEMBL957
DrugBank DB00559
DrugCentral 392
EPA CompTox DTXSID7046627
FDA SRS XUL93R30K2
Human Metabolome Database HMDB0014699
Guide to Pharmacology 3494
PDB K86
PharmGKB PA10034
SureChEMBL SCHEMBL4218
ZINC ZINC000001538857
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