MedKoo Cat#: 317331 | Name: Bosentan
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Bosentan is a mixed Endothelin Receptor Antagonist which is used as a vasodilator. Bosentan is an inhibitor of ETAR and ETBR. It is used for the treatment of pulmonary artery hypertension (PAH). Bosentan blocks the action of endothelin molecules that would otherwise promote narrowing of the blood vessels and lead to high blood pressure.

Chemical Structure

Bosentan
Bosentan
CAS#147536-97-8 (free)

Theoretical Analysis

MedKoo Cat#: 317331

Name: Bosentan

CAS#: 147536-97-8 (free)

Chemical Formula: C27H29N5O6S

Exact Mass: 551.1839

Molecular Weight: 551.61

Elemental Analysis: C, 58.79; H, 5.30; N, 12.70; O, 17.40; S, 5.81

Price and Availability

Size Price Availability Quantity
50mg USD 350.00 2 Weeks
100mg USD 600.00 2 Weeks
200mg USD 950.00 2 Weeks
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Related CAS #
147536-97-8 (Bosentan free) 157212-55-0 (Bosentan hydrate)
Synonym
Bosentan; bosentan anhydrous; bosentan monohydrate; Ro 47-0203; Ro-47-0203; Tracleer; Ro-47-0203.
IUPAC/Chemical Name
4-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-pyrimidin-2-ylpyrimidin-4-yl]benzenesulfonamide
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)
SMILES Code
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
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Related: 147536-97-8 (Bosentan free) 157212-55-0 (Bosentan hydrate).
Certificate of Analysis
Safety Data Sheet (SDS)

Preparing Stock Solutions

The following data is based on the product molecular weight 551.61 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Joyeux-Faure M, Jullian-Desayes I, Pepin JL, Cracowski JL, Baguet JP, Tamisier R, Levy P, Godin-Ribuot D, Launois SH. Comparison of continuous positive airway pressure and bosentan effect in mildly hypertensive patients with obstructive sleep apnoea: A randomized controlled pilot study. Respirology. 2015 Dec 8. doi: 10.1111/resp.12713. [Epub ahead of print] PubMed PMID: 26643404. 2: Bellando-Randone S, Lepri G, Bruni C, Blagojevic J, Radicati A, Cometi L, De Paulis A, Matucci-Cerinic M, Guiducci S. Combination therapy with Bosentan and Sildenafil improves Raynaud's phenomenon and fosters the recovery of microvascular involvement in systemic sclerosis. Clin Rheumatol. 2015 Dec 3. [Epub ahead of print] PubMed PMID: 26631100. 3: Avdeev SN. [Approaches to therapy for pulmonary hypertension: Role of the endothelin receptor antagonist bosentan]. Ter Arkh. 2015;87(9):64-71. Russian. PubMed PMID: 26591555. 4: Enderle Y, Meid AD, Friedrich J, Grünig E, Wilkens H, Haefeli WE, Burhenne J. Dried Blood Spot Technique for the Monitoring of Ambrisentan, Bosentan, Sildenafil, and Tadalafil in Patients with Pulmonary Arterial Hypertension. Anal Chem. 2015 Dec 3. [Epub ahead of print] PubMed PMID: 26583764. 5: Matsunaga N, Kaneko N, Staub AY, Nakanishi T, Nunoya K, Imawaka H, Tamai I. Analysis of the Metabolic Pathway of Bosentan and of the Cytotoxicity of Bosentan Metabolites Based on a Quantitative Modeling of Metabolism and Transport in Sandwich-Cultured Human Hepatocytes. Drug Metab Dispos. 2016 Jan;44(1):16-27. doi: 10.1124/dmd.115.067074. Epub 2015 Oct 26. PubMed PMID: 26502773. 6: Zahedi A, Nematbakhsh M, Moeini M, Talebi A. Role of endothelin receptor antagonist; bosentan in cisplatin-induced nephrotoxicity in ovariectomized estradiol treated rats. J Nephropathol. 2015 Oct;4(4):134-40. doi: 10.12860/jnp.2015.25. Epub 2015 Oct 1. PubMed PMID: 26457261; PubMed Central PMCID: PMC4596298. 7: Amin A, Mohamadifar A, Taghavi S, Naderi N, Sadeghi H. Lower Doses of Bosentan in Combination With Sildenafil Might be Beneficial in Pulmonary Arterial Hypertension. Res Cardiovasc Med. 2015 Aug 1;4(3):e26487. doi: 10.5812/cardiovascmed.26487v2. eCollection 2015 Aug. PubMed PMID: 26436071; PubMed Central PMCID: PMC4588707. 8: Berger RM, Haworth SG, Bonnet D, Dulac Y, Fraisse A, Galiè N, Ivy DD, Jaïs X, Miera O, Rosenzweig EB, Efficace M, Kusic-Pajic A, Beghetti M. FUTURE-2: Results from an open-label, long-term safety and tolerability extension study using the pediatric FormUlation of bosenTan in pUlmonary arterial hypeRtEnsion. Int J Cardiol. 2016 Jan 1;202:52-8. doi: 10.1016/j.ijcard.2015.08.080. Epub 2015 Aug 9. PubMed PMID: 26386921. 9: Taquin H, Lacour JP, Le Duff F, Chiaverini C, Passeron T. Treatment of resistant port-wine stains with bosentan and pulsed dye laser: a pilot prospective study. J Eur Acad Dermatol Venereol. 2015 Aug 24. doi: 10.1111/jdv.13275. [Epub ahead of print] PubMed PMID: 26304141. 10: Masarwa R, Shamriz O, Zilkha A, Braun J, Kleid DM, Weintraub M, Schulz A, Stepensky P. Bosentan-induced Reduction in Cyclosporine-A Levels: A Rare Interaction in an Infant With Osteopetrosis and Severe Pulmonary Hyperetension. J Pediatr Hematol Oncol. 2015 Oct;37(7):573-4. doi: 10.1097/MPH.0000000000000409. PubMed PMID: 26274036. 11: Serafim KG, Navarro SA, Zarpelon AC, Pinho-Ribeiro FA, Fattori V, Cunha TM, Alves-Filho JC, Cunha FQ, Casagrande R, Verri WA Jr. Bosentan, a mixed endothelin receptor antagonist, inhibits superoxide anion-induced pain and inflammation in mice. Naunyn Schmiedebergs Arch Pharmacol. 2015 Nov;388(11):1211-21. doi: 10.1007/s00210-015-1160-z. Epub 2015 Aug 6. PubMed PMID: 26246053. 12: Sebastiani M, Manfredi A, Cestelli V, Praino E, Cannarile F, Giuggioli D, Colaci M, Ferri C. Validation study of predictive value of capillaroscopic skin ulcer risk index (CSURI) in scleroderma patients treated with bosentan. Clin Exp Rheumatol. 2015 Jul-Aug;33(4 Suppl 91):S196. Epub 2015 Aug 5. PubMed PMID: 26242501. 13: Iglarz M, Landskroner K, Bauer Y, Vercauteren M, Rey M, Renault B, Studer R, Vezzali E, Freti D, Hadana H, Schläpfer M, Cattaneo C, Bortolamiol C, Weber E, Whitby BR, Delahaye S, Wanner D, Steiner P, Nayler O, Hess P, Clozel M. Comparison of Macitentan and Bosentan on Right Ventricular Remodeling in a Rat Model of Non-vasoreactive Pulmonary Hypertension. J Cardiovasc Pharmacol. 2015 Nov;66(5):457-67. doi: 10.1097/FJC.0000000000000296. PubMed PMID: 26230396; PubMed Central PMCID: PMC4632117. 14: Sharabi I, Tanay A, Zandman-Goddard G. Digital Ulcers, Systemic Sclerosis Sine Scleroderma and Paraneoplastic Phenomena Responding to Bosentan Therapy. Isr Med Assoc J. 2015 Feb;17(2):126-7. PubMed PMID: 26223094. 15: Rotondo C, Praino E, Nivuori M, Di Serio F, Lapadula G, Iannone F. No changes in N-terminal pro-brain natriuretic peptide in a longitudinal cohort of patients with systemic sclerosis-associated pulmonary arterial hypertension on therapy with bosentan. Int J Rheum Dis. 2015 Jul 28. doi: 10.1111/1756-185X.12721. [Epub ahead of print] PubMed PMID: 26218502. 16: McLaughlin V, Channick RN, Ghofrani HA, Lemarié JC, Naeije R, Packer M, Souza R, Tapson VF, Tolson J, Al Hiti H, Meyer G, Hoeper MM. Bosentan added to sildenafil therapy in patients with pulmonary arterial hypertension. Eur Respir J. 2015 Aug;46(2):405-13. doi: 10.1183/13993003.02044-2014. Epub 2015 Jun 25. PubMed PMID: 26113687. 17: Romano E, Bellando-Randone S, Manetti M, Bruni C, Lepri G, Matucci-Cerinic M, Guiducci S. Bosentan blocks the antiangiogenic effects of sera from systemic sclerosis patients: an in vitro study. Clin Exp Rheumatol. 2015 Jul-Aug;33(4 Suppl 91):S148-52. Epub 2015 Jun 19. PubMed PMID: 26088817. 18: Muraoka H, Imamura T, Hatano M, Maki H, Yao A, Kinugawa K, Komuro I. Secure Combination Therapy With Low-Dose Bosentan and Ambrisentan to Treat Portopulmonary Hypertension Minimizing Each Adverse Effect. Int Heart J. 2015;56(4):471-3. doi: 10.1536/ihj.15-007. Epub 2015 Jun 18. PubMed PMID: 26084462. 19: Doganci S, Yildirim V, Yesildal F, Erol G, Kadan M, Ozkan G, Avcu F, Ozgurtas T. Comparison of angiogenic and proliferative effects of three commonly used agents for pulmonary artery hypertension (sildenafil, iloprost, bosentan): is angiogenesis always beneficial? Eur Rev Med Pharmacol Sci. 2015 May;19(10):1900-6. PubMed PMID: 26044238. 20: Onda N, Tanaka Y, Hino M, Gemma A. Bosentan for pulmonary hypertension secondary to idiopathic pulmonary fibrosis. Respir Med Case Rep. 2014 Dec 16;14:19-23. doi: 10.1016/j.rmcr.2014.11.008. eCollection 2015. PubMed PMID: 26029570; PubMed Central PMCID: PMC4356039.