Tezosentan | 180384-57-0 | ETA and ETB antagonist

MedKoo Cat#: 326695 | Name: Tezosentan

Description:

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

Tezosentan is a non-selective ETA and ETB receptor antagonist. It acts as a vasodilator and was designed as a therapy for patients with acute heart failure. Tezosentan inhibits uptake of proinflammatory endothelin-1 in stenotic aortic valves. Tezosentan increases nitric oxide signaling via enhanced hydrogen peroxide generation in lambs with surgically induced acute increases in pulmonary blood flow. Tezosentan reduces the renal injury induced by abdominal aortic ischemia-reperfusion in rats.

Chemical Structure

Tezosentan

CAS#180384-57-0

Theoretical Analysis

MedKoo Cat#: 326695

Name: Tezosentan

CAS#: 180384-57-0

Chemical Formula: C27H27N9O6S

Exact Mass: 605.1805

Molecular Weight: 605.63

Elemental Analysis: C, 53.55; H, 4.49; N, 20.82; O, 15.85; S, 5.29

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Tezosentan; RO 610612; RO-610612; RO 610612; Ro 61-6612; Ro-61-6612; Ro61-6612; ACT 050089; ACT-050089; ACT050089;

IUPAC/Chemical Name

N-(6-(2-Hydroxyethoxy)-5-(2-methoxyphenoxy)-2-(2-(1H-tetrazol-5-yl)-4-pyridinyl)-4-pyrimidinyl)-5-(1-methylethyl)-2-pyridinesulfonamide

InChi Key

TUYWTLTWNJOZNY-UHFFFAOYSA-N

InChi Code

InChI=1S/C27H27N9O6S/c1-16(2)18-8-9-22(29-15-18)43(38,39)34-26-23(42-21-7-5-4-6-20(21)40-3)27(41-13-12-37)31-24(30-26)17-10-11-28-19(14-17)25-32-35-36-33-25/h4-11,14-16,37H,12-13H2,1-3H3,(H,30,31,34)(H,32,33,35,36)

SMILES Code

O=S(C1=NC=C(C(C)C)C=C1)(NC2=NC(C3=CC(C4=NN=NN4)=NC=C3)=NC(OCCO)=C2OC5=CC=CC=C5OC)=O

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 605.63 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.

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: Mommerot A, Denault AY, Dupuis J, Carrier M, Perrault LP. Cardiopulmonary bypass is associated with altered vascular reactivity of isolated pulmonary artery in a porcine model: therapeutic potential of inhaled tezosentan. J Cardiothorac Vasc Anesth. 2014 Jun;28(3):698-708. doi: 10.1053/j.jvca.2013.12.013. PubMed PMID: 24917060. 2: Denault AY, Pearl RG, Michler RE, Rao V, Tsui SS, Seitelberger R, Cromie M, Lindberg E, D'Armini AM. Tezosentan and right ventricular failure in patients with pulmonary hypertension undergoing cardiac surgery: the TACTICS trial. J Cardiothorac Vasc Anesth. 2013 Dec;27(6):1212-7. doi: 10.1053/j.jvca.2013.01.023. Epub 2013 Mar 21. PubMed PMID: 23523254. 3: Kumar S, Oishi PE, Rafikov R, Aggarwal S, Hou Y, Datar SA, Sharma S, Azakie A, Fineman JR, Black SM. Tezosentan increases nitric oxide signaling via enhanced hydrogen peroxide generation in lambs with surgically induced acute increases in pulmonary blood flow. J Cell Biochem. 2013 Feb;114(2):435-47. doi: 10.1002/jcb.24383. PubMed PMID: 22961736; PubMed Central PMCID: PMC3906673. 4: Leskelä HV, Vuolteenaho O, Koivula MK, Taskinen P, Ruskoaho H, Peltonen T, Lehenkari P. Tezosentan inhibits uptake of proinflammatory endothelin-1 in stenotic aortic valves. J Heart Valve Dis. 2012 Jan;21(1):23-30. PubMed PMID: 22474738. 5: Lourenço AP, Vasques-Nóvoa F, Oliveira-Pinto J, Fontoura D, Roncon-Albuquerque R Jr, Leite-Moreira AF. Haemodynamic and neuroendocrine effects of tezosentan in chronic experimental pulmonary hypertension. Intensive Care Med. 2012 Jun;38(6):1050-60. doi: 10.1007/s00134-012-2484-5. Epub 2012 Feb 14. PubMed PMID: 22349420. 6: Atalay F, Yurdakan G, Yilmaz-Sipahi E. Effect of the endothelin receptor antagonist tezosentan on alpha-naphthylthiourea-induced lung injury in rats. Kaohsiung J Med Sci. 2012 Feb;28(2):72-8. doi: 10.1016/j.kjms.2011.10.019. Epub 2012 Jan 14. PubMed PMID: 22313533. 7: Lebrec D, Bosch J, Jalan R, Dudley FJ, Jessic R, Moreau R, Garcia-Pagan JC, Mookerjee RP, Chiossi E, Van Giersbergen PL, Kusic-Pajic A, Dingemanse J. Hemodynamics and pharmacokinetics of tezosentan, a dual endothelin receptor antagonist, in patients with cirrhosis. Eur J Clin Pharmacol. 2012 May;68(5):533-41. doi: 10.1007/s00228-011-1157-6. Epub 2011 Nov 20. PubMed PMID: 22101624. 8: Hedelin P, Kylhammar D, Rådegran G. Dual endothelin receptor blockade with tezosentan markedly attenuates hypoxia-induced pulmonary vasoconstriction in a porcine model. Acta Physiol (Oxf). 2012 Mar;204(3):419-34. doi: 10.1111/j.1748-1716.2011.02339.x. Epub 2011 Aug 12. PubMed PMID: 21726419. 9: Ruane-O'Hora T, Rae MG, Markos F. Effect of clazosentan, a selective endothelin A receptor antagonist, and tezosentan, a dual endothelin A/B antagonist, on pulsatile shear stress induced constriction of the iliac in the anaesthetized pig. Clin Exp Pharmacol Physiol. 2011 Aug;38(8):515-20. doi: 10.1111/j.1440-1681.2011.05540.x. PubMed PMID: 21575033. 10: Ryu SM, Kim HJ, Cho KR, Jo WM. Myocardial protective effect of tezosentan, an endothelin receptor antagonist, for ischemia-reperfusion injury in experimental heart failure models. J Korean Med Sci. 2009 Oct;24(5):782-8. doi: 10.3346/jkms.2009.24.5.782. Epub 2009 Sep 23. PubMed PMID: 19794971; PubMed Central PMCID: PMC2752756. 11: Gulmen S, Kiris I, Narin C, Ceylan BG, Mermi B, Sutcu R, Meteoglu I. Tezosentan reduces the renal injury induced by abdominal aortic ischemia-reperfusion in rats. J Surg Res. 2009 Nov;157(1):e7-e13. doi: 10.1016/j.jss.2008.08.011. Epub 2008 Oct 24. PubMed PMID: 19329125. 12: Dingemanse J, Halabi A, van Giersbergen PL. Influence of liver cirrhosis on the pharmacokinetics, pharmacodynamics, and safety of tezosentan. J Clin Pharmacol. 2009 Apr;49(4):455-64. doi: 10.1177/0091270008330157. PubMed PMID: 19318695. 13: Persson BP, Rossi P, Weitzberg E, Oldner A. Inhaled tezosentan reduces pulmonary hypertension in endotoxin-induced lung injury. Shock. 2009 Oct;32(4):427-34. doi: 10.1097/SHK.0b013e31819e2cbb. PubMed PMID: 19197226. 14: Kiriş I, Narin C, Gülmen S, Yilmaz N, Sütçü R, Kapucuoğlu N. Endothelin receptor antagonism by tezosentan attenuates lung injury induced by aortic ischemia-reperfusion. Ann Vasc Surg. 2009 May-Jun;23(3):382-91. doi: 10.1016/j.avsg.2008.10.003. Epub 2009 Jan 9. PubMed PMID: 19135850. 15: Aneman A, Treggiari MM, Burgener D, Laesser M, Strasser S, Hadengue A. Tezosentan normalizes hepatomesenteric perfusion in a porcine model of cardiac tamponade. Acta Anaesthesiol Scand. 2009 Feb;53(2):203-9. doi: 10.1111/j.1399-6576.2008.01834.x. Epub 2008 Dec 15. PubMed PMID: 19094177. 16: Farmer DG, Kaldas F, Anselmo D, Katori M, Shen XD, Lassman C, Kaldas M, Clozel M, Busuttil RW, Kupiec-Weglinski J. Tezosentan, a novel endothelin receptor antagonist, markedly reduces rat hepatic ischemia and reperfusion injury in three different models. Liver Transpl. 2008 Dec;14(12):1737-44. doi: 10.1002/lt.21621. PubMed PMID: 19025917; PubMed Central PMCID: PMC2975480. 17: Fenhammar J, Andersson A, Frithiof R, Forestier J, Weitzberg E, Sollevi A, Hjelmqvist H. The endothelin receptor antagonist tezosentan improves renal microcirculation in a porcine model of endotoxemic shock. Acta Anaesthesiol Scand. 2008 Nov;52(10):1385-93. doi: 10.1111/j.1399-6576.2008.01768.x. PubMed PMID: 19025532. 18: Narin C, Kiris I, Gülmen S, Toy H, Yilmaz N, Sütcü R. Endothelin receptor blockade with tezosentan ameliorates myocardial injury induced by abdominal aortic ischemia-reperfusion. Tohoku J Exp Med. 2008 Nov;216(3):267-76. PubMed PMID: 18987461. 19: Geiger R, Treml B, Kleinsasser A, Neu N, Fischer V, Stein JI, Loeckinger A. Intravenous tezosentan and vardenafil attenuate acute hypoxic pulmonary hypertension. High Alt Med Biol. 2008 Fall;9(3):223-7. doi: 10.1089/ham.2008.1024. PubMed PMID: 18800959. 20: Andersson A, Fenhammar J, Frithiof R, Weitzberg E, Sollevi A, Hjelmqvist H. Mixed endothelin receptor antagonism with tezosentan improves intestinal microcirculation in endotoxemic shock. J Surg Res. 2008 Sep;149(1):138-47. doi: 10.1016/j.jss.2007.12.751. Epub 2008 Jan 11. PubMed PMID: 18639249.