Bosentan

Alias: Ro-47-0203; Ro47-0203; bosentan anhydrous; Ro 47-0203; bosentan monohydrate; Ro47 0203; Ro-47 0203; Tracleer
Cat No.:V1513 Purity: ≥98%
Bosentan (formerly Ro 47-0203; brand name Tracleer) is a potent, competitive and dual antagonist of endothelin (ET) receptor with anti-hypertensive activity.
Bosentan Chemical Structure CAS No.: 147536-97-8
Product category: Endothelin Receptor
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
25mg
50mg
100mg
250mg
500mg
1g
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Other Forms of Bosentan:

  • Bosentan-d4
  • Bosentan Hydrate (Ro 47-0203)
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Bosentan (formerly Ro 47-0203; brand name Tracleer) is a potent, competitive and dual antagonist of endothelin (ET) receptor with anti-hypertensive activity. It inhibits ET-A and ET-B with Ki values of 4.7 nM and 95 nM, respectively. Bosentan is used to treat pulmonary arterial hypertension (PAH) as a vasodilator.

Biological Activity I Assay Protocols (From Reference)
Targets
ETA receptor ( Ki = 4.7 nM ); ETA receptor ( Ki = 95 nM )
ln Vitro

In vitro activity: Bosentan (BOS) selectively and competitively inhibits the binding of 125I-labeled ET-1 to human placenta cells' ETB receptors and human smooth muscle cells' ETA receptors. Bosentan exhibits an in vitro binding affinity of 4.7 nM for ETA receptors on human SMC and 41 or 95 nM for ETB receptors on human SMC or placenta cells. In an in vitro 125I-labeling assay, bosentan has 67-fold higher selectivity for ETA than ETB receptors (mean IC50=7.1 vs 474.8 nM)[1].

ln Vivo
Macitentan 30 mg/kg, when administered in addition to Bosentan 100 mg/kg, reduces mean arterial blood pressure (MAP) in hypertensive rats by an additional 19 mm Hg. Bosentan, on the other hand, does not cause an extra MAP decrease when taken in addition to Macitentan. Compared to a maximal effective dose of Bosentan, which is administered on top of Macitentan, there is no additional decrease in mean pulmonary artery pressure (MPAP) in pulmonary hypertensive rats when Macitentan 30 mg/kg is added[3].
Cell Assay
The trypan blue exclusion test is used to assess the viability of cells. Bosentan is added to human dermal fibroblasts at the recommended concentrations (10, 20 and 40 μM). After 24 and 48 hours, cell viability is assessed. A hematocytometer is used to count both stained (dead) and unstained (viable) cells[2].
Animal Protocol
Rats: Rats that are two months old—DSS and Wistar—are employed. Doses ranging from 0.1 to 100 mg/kg (Macitentan) or 3 to 600 mg/kg (Bosentan) are used to measure the pharmacological effects on heart rate (HR), mean arterial pressure (MAP), or mean pulmonary arterial pressure (MPAP), and up to 120 hours after a single gavage. 1) Macitentan is given on top of the maximum effective dose of Bosentan determined by the dose-response curve in order to assess whether Macitentan can offer greater pharmacological activity compared to Bosentan. Secondly, the maximum effective dose of Macitentan is topped off with the same dose of Bosentan. Tmax of the first tested compound is the point at which the second compound's maximal effective dose is given.
References

[1]. Bosentan: a review of its use in the management of mildly symptomatic pulmonary arterial hypertension. Am J Cardiovasc Drugs. 2009;9(5):331-50.

[2]. Bosentan reverses the pro-fibrotic phenotype of systemic sclerosis dermal fibroblasts via increasing DNA binding ability of transcription factor Fli1. Arthritis Res Ther. 2014 Apr 3;16(2):R86.

[3]. Comparison of pharmacological activity of macitentan and bosentan in preclinical models of systemic and pulmonary hypertension. Life Sci. 2014 Nov 24;118(2):333-9.

[4]. Endothelin Regulates Porphyromonas gingivalis-Induced Production of Inflammatory Cytokines. PLoS One. 2016 Dec 28;11(12):e0167713.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C27H29N5O6S
Molecular Weight
551.61
Exact Mass
551.18
Elemental Analysis
C, 58.79; H, 5.30; N, 12.70; O, 17.40; S, 5.81
CAS #
147536-97-8
Appearance
Solid powder
SMILES
CC(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC2=C(C(=NC(=N2)C3=NC=CC=N3)OCCO)OC4=CC=CC=C4OC
InChi Key
GJPICJJJRGTNOD-UHFFFAOYSA-N
InChi Code
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)
Chemical Name
4-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-pyrimidin-2-ylpyrimidin-4-yl]benzenesulfonamide
Synonyms
Ro-47-0203; Ro47-0203; bosentan anhydrous; Ro 47-0203; bosentan monohydrate; Ro47 0203; Ro-47 0203; Tracleer
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: ~100 mg/mL (~181.3 mM)
Water: <1 mg/mL
Ethanol: ~3 mg/mL (~5.4 mM)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.8129 mL 9.0644 mL 18.1288 mL
5 mM 0.3626 mL 1.8129 mL 3.6258 mL
10 mM 0.1813 mL 0.9064 mL 1.8129 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

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Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT02116335 Active
Recruiting
Drug: Bosentan
Drug: Placebo
Hypertension Augusta University June 2015 Not Applicable
NCT05657613 Active
Recruiting
Drug: Part 2 -Group A Bosentan
125 mg (CYP450 3A4 inducer)
with Pacritinib
Drug Interactions CTI BioPharma January 3, 2023 Phase 1
NCT02377271 Recruiting Drug: bosentan
Drug: placebo
Ischemic Optic Neuropathy University Hospital, Grenoble August 2015 Phase 3
NCT04158635 Recruiting Drug: Bosentan
Drug: Gemcitabine
Drug: Nab-paclitaxel
Stage III Pancreatic Cancer
AJCC v8
Stage IV Pancreatic Cancer
AJCC v8
City of Hope Medical Center September 1, 2021 Phase 1
NCT04039464 Recruiting Drug: Duo-Therapy with
Sildenafil + Bosentan
Pediatric Pulmonary
Hypertension
Johns Hopkins University August 1, 2022 Phase 3
Biological Data
  • Bosentan reversed the pro-fibrotic phenotype of systemic sclerosis (SSc) dermal fibroblasts via increasing the DNA binding of Fli1. Arthritis Res Ther . 2014 Apr 3;16(2):R86.
  • Bosentan prevented the development of dermal fibrosis, at least partially, by increasing the expression of Fli1 protein in lesional dermal fibroblasts of bleomycin (BLM)-induced systemic sclerosis (SSc) murine model. Arthritis Res Ther . 2014 Apr 3;16(2):R86.
  • Absence of pharmacological activity of bosentan on top of macitentan in conscious Dahl-salt sensitive rats. Life Sci . 2014 Nov 24;118(2):333-9.
  • Superior pharmacological effect of macitentan on top of bosentan in conscious bleomycin-induced pulmonary hypertensive rats. Life Sci . 2014 Nov 24;118(2):333-9.
  • Experimental design and time schedule. Ligature was placed on day 0, and bosentan was treated 1 day before ligature ligation (-1 day). PLoS One . 2016 Dec 28;11(12):e0167713.
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