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SML1265

Sigma-Aldrich

Bosentan hydrate

≥98% (HPLC)

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Synonym(s):
4-(1,1-Dimethylethyl)-N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)[2,2′-bipyrimidin]-4-yl]benzenesulfonamide monohydrate, 4-Tert-butyl-N- [6-(2-hydroxyethoxy)-5-(2-methoxy-phenoxy)-[2,2´]-bipyrimidin-4-yl]-benzenesulfonamide monohydrate, Ro-47-0203
Empirical Formula (Hill Notation):
C27H29N5O6S · H2O
CAS Number:
157212-55-0
Molecular Weight:
569.63
MDL number:
MFCD09751188
UNSPSC Code:
12352200
PubChem Substance ID:
329825756
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

O=S(C1=CC=C(C(C)(C)C)C=C1)(NC2=NC(C3=NC=CC=N3)=NC(OCCO)=C2OC4=CC=CC=C4OC)=O.O

InChI

1S/C27H29N5O6S.H2O/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);1H2

InChI key

SXTRWVVIEPWAKM-UHFFFAOYSA-N

Application

Bosentan hydrate has been used in cell viability assay. It has also been used as a positive control for calcium transient analysis.

Biochem/physiol Actions

Bosentan is an endothelin receptor antagonist. Endothelin is a potent vasoconstrictor, making antagonists of clinical interest for the treatment of conditions associated with vasospasm, such as subarachnoid hemorrhage (SAH) and hypertension. Bosentan is a dual endothelin receptor antagonist effective in the treatment of pulmonary arterial hypertension (PAH), the first of the class to make it to market. Bosentan is an orally available, competitive antagonist of both the ETA and ETB receptor subtypes with a Ki of 4.7 nM for ETA and a Ki of 95 nM for ETB.
Bosentan is found to decrease deposition of collagen in the lungs, which has been observed in bleomycin-induced pulmonary fibrosis rat model.

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H361fd,H412

Hazard Classifications

Aquatic Chronic 3 - Repr. 2

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Endothelin-1 receptor blockade as new possible therapeutic approach in multiple myeloma.
Russignan A, et al.
British Journal of Haematology, 178(5), 781-793 (2017)
BUILD-1: a randomized placebo-controlled trial of bosentan in idiopathic pulmonary fibrosis.
King Jr T E, et al.
American Journal of Respiratory and Critical Care Medicine, 177(1), 75-81 (2008)
Molecular phenotyping combines molecular information, biological relevance, and patient data to improve productivity of early drug discovery.
Drawnel F M, et al.
Cell Chemical Biology, 24(5), 624-634 (2017)
Xiaomin Liang et al.
Drug metabolism and disposition: the biological fate of chemicals, 48(12), 1283-1292 (2020-10-11)
It is well documented that human hepatic clearance based on in vitro metabolism or transporter assays systematically resulted in underprediction; therefore, large empirical scalars are often needed in either static or physiologically based pharmacokinetic (PBPK) models to accurately predict human
Fuhua Yang et al.
Toxicological sciences : an official journal of the Society of Toxicology, 170(1), 95-108 (2019-04-16)
The bile salt export pump (BSEP, ABCB11) mediates bile acid efflux from hepatocytes into bile. Although the inhibition of BSEP has been implicated as an important mechanism of drug-induced liver injury (DILI), liver injury caused by BSEP-inhibiting drugs is rarely
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