Bosentan (CED0003394)

Record Information

Version

1.0

Creation Date

2016-05-22 05:50:57 UTC

Update Date

2026-08-22 07:26:47 UTC

Accession Number

CHEM019132

Identification

Common Name

Bosentan

Class

Small Molecule

Description

Bosentan is an organic compound with the chemical formula C27H29N5O6S. Bosentan belongs to the pyrimidines and pyrimidine derivatives, a subclass of diazines within the organic compounds. With an average molecular weight of 551.61 g/mol, Bosentan is a heavy molecule. Within the hierarchy of chemical classification, it is further categorized under the superclass of organoheterocyclic compounds. The compound acts on two recorded protein targets, serving as an antagonist of the Endothelin receptor type B (EDNRB) and the Endothelin-1 receptor (EDNRA). Bosentan is associated with four recorded sources. These include pharmaceuticals and veterinary products, specifically within the categories of gynecologicals and antihypertensives, as well as household cleaning and consumer products such as non electric simulated smoking devices. Additionally, it is found in electrical and electronic equipment, specifically television systems. The recorded route of exposure for this compound is oral.

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
4-(1,1-Dimethylethyl)-N-(6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-(2,2'-bipyrimidin)-4-yl) benzenesulfornamide	ChEBI
Bosentanum	ChEBI
p-Tert-butyl-N-(6-(2-hydroxyethoxy)-5-(O-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl)benzenesulfonamide	ChEBI
4-(1,1-Dimethylethyl)-N-(6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-(2,2'-bipyrimidin)-4-yl) benzenesulphornamide	Generator
p-Tert-butyl-N-(6-(2-hydroxyethoxy)-5-(O-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl)benzenesulphonamide	Generator
Bosentan hydrate	HMDB
4-t-Butyl-N-(6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl)benzenesulfonamide	HMDB
Bosentan monohydrate	HMDB
Bosentan anhydrous	HMDB
Tracleer	HMDB

Chemical Formula

C₂₇H₂₉N₅O₆S

Average Molecular Mass

551.614 g/mol

Monoisotopic Mass

551.184 g/mol

CAS Registry Number

147536-97-8

IUPAC Name

4-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-(pyrimidin-2-yl)pyrimidin-4-yl]benzene-1-sulfonamide

Traditional Name

bosentan

SMILES

COC1=CC=CC=C1OC1=C(NS(=O)(=O)C2=CC=C(C=C2)C(C)(C)C)N=C(N=C1OCCO)C1=NC=CC=N1

InChI Identifier

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)

InChI Key

GJPICJJJRGTNOD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bipyrimidines and oligopyrimidines. These are organic compounds containing two or more pyrimidine rings directly linked to each other. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Bipyrimidines and oligopyrimidines

Alternative Parents

Substituents

Bipyrimidine
Diaryl ether
Benzenesulfonamide
Benzenesulfonyl group
Phenylpropane
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Alkyl aryl ether
Monocyclic benzene moiety
Imidolactam
Benzenoid
Organosulfonic acid amide
Heteroaromatic compound
Aminosulfonyl compound
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Azacycle
Ether
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Primary alcohol
Organic oxygen compound
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

sulfonamide (CHEBI:51450 )
pyrimidines (CHEBI:51450 )
primary alcohol (CHEBI:51450 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.009 g/L	ALOGPS
logP	4.18	ALOGPS
logP	4.94	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	5.8	ChemAxon
pKa (Strongest Basic)	-0.43	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	145.65 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	166.66 m³·mol⁻¹	ChemAxon
Polarizability	57.89 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0k9f-1404490000-6d317563fca85570bb94	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0ab9-8400329000-23bc8d319fee004b04e7	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udj-0810090000-b97444dff91ec725276d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-1690040000-c561d9dbb5ed88285519	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0290000000-917fcf22a5648855f494	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0000090000-804fbcd24b248dea41cb	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0000090000-37d3e81ca9fac1bb8607	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0032090000-6b8d5527e6d09bf8bd93	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0192000000-ac3f1b4e6b6da63962f7	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-1690040000-53b916bf54d069a5d9af	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udj-0700090000-a1325fb53ae46b3119a0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0020190000-45fdf2d2b678882a2c9a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01r2-7853970000-73d404cdce8bec564973	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0zmr-4911000000-355d0a86f2c020114251	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-1111090000-838b3a76b34448d48154	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00b9-1938000000-4a504df1e7892ab5ed7b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03g3-8592000000-757b42467cf720e1d98b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0000090000-0264cc47a8b7eb39ffb5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0pb9-0200190000-c06202aa662980be16e4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0ab9-6900720000-9771730325d97d3f1f0f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0000090000-12b263be07bc58a79d77	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0zfu-0101490000-41d3bf6ec3c473268216	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udj-0223930000-515898571490d1845bf8	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
8975.0	Log mg/kg	[5000:16000]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
289	Antihypertensives	Healthcare, pharmaceuticals & veterinary products	Not Available
316	Gynecologicals	Healthcare, pharmaceuticals & veterinary products	Not Available
537	Television Systems	Electrical & Electronic Equipment	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
601	Lawn Mowers	Agriculture & land management	Not Available

Pathways

1 pathway

Bosentan Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Endothelin-1 receptor	P25101	Humans	Predicted (SEA)	2.95827
Click to view 3D structure	Endothelin receptor type B	P24530	Humans	Predicted (SEA)	1.47914
Click to view 3D structure	Endothelin-1 receptor	P26684	Rattus norvegicus	Predicted (SEA)	1.32344
Click to view 3D structure	Endothelin-1 receptor	Q29010	Sus scrofa	Predicted (SEA)	0.856341
Click to view 3D structure	Endothelin receptor type B	P21451	Rattus norvegicus	Predicted (SEA)	4.98235
Click to view 3D structure	Nuclear receptor subfamily 1 group I member 2	O75469	Humans	Predicted (SEA)	10.1982
Click to view 3D structure	Cytochrome b-c1 complex subunit 7	P14927	Humans	Predicted (SEA)	10.7432
Click to view 3D structure	C-C chemokine receptor type 2	P41597	Humans	Predicted (SEA)	58.2312
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	1649.39
Click to view 3D structure	Extracellular serine/threonine protein kinase FAM20C	Q8IXL6	Humans	Predicted (SEA)	22.187
Click to view 3D structure	C-C chemokine receptor type 4	P51679	Humans	Predicted (SEA)	22.8877
Click to view 3D structure	Type-1 angiotensin II receptor	P30556	Humans	Predicted (SEA)	253.166
Click to view 3D structure	Bromodomain-containing protein 4	O60885	Humans	Predicted (SEA)	358.34
Click to view 3D structure	Sodium channel protein type 9 subunit alpha	Q15858	Humans	Predicted (SEA)	243.435
Click to view 3D structure	Proto-oncogene tyrosine-protein kinase Src	P12931	Humans	Predicted (SEA)	1862.93
Click to view 3D structure	Tyrosine-protein kinase SYK	P43405	Humans	Predicted (SEA)	1381.59
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	804.416
Click to view 3D structure	Streptokinase A	P10520	Streptococcus pyogenes serotype M1	Predicted (SEA)	550.16
Click to view 3D structure	Sodium channel protein type 9 subunit alpha	Q62205	Mus musculus	Predicted (SEA)	123.313
Click to view 3D structure	Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	Humans	Predicted (SEA)	899.081
Click to view 3D structure	Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	P42336	Humans	Predicted (SEA)	1117.21
Click to view 3D structure	Mast/stem cell growth factor receptor Kit	P10721	Humans	Predicted (SEA)	2079.9
Click to view 3D structure	Glycogen synthase kinase-3 alpha	P49840	Humans	Predicted (SEA)	1976.83
Click to view 3D structure	C-C chemokine receptor type 4	Q8MJW8	Canis lupus familiaris	Predicted (SEA)	14.3243
Click to view 3D structure	Mitogen-activated protein kinase 14	Q16539	Humans	Predicted (SEA)	1885.74