Cinaciguat

• CAT Number: I006133
• CAS Number: 329773-35-5 (free)
• Molecular Formula: C36H39NO5
• Molecular Weight: 565.71
• Purity: ≥95%
• Synonyms: BAY 582667; BAY-582667; BAY582667; BAY 58-2667; BAY-58-2667; BAY58-2667; Cinaciguat;2-(((4-carboxybutyl)(2-((4-phenethylbenzyl)oxy)phenethyl)amino)methyl)benzoic acid
• Solubility: Soluble in DMSO, not in water
• Storage: 0 - 4°C for short term ,or -20 °C for long term
• InChI: InChI=1S/C36H39NO5/c38-35(39)16-8-9-24-37(26-32-13-4-6-14-33(32)36(40)41)25-23-31-12-5-7-15-34(31)42-27-30-21-19-29(20-22-30)18-17-28-10-2-1-3-11-28/h1-7,10-15,19-22H,8-9,16-18,23-27H2,(H,38,39)(H,40,41)
• InChIKey: IUKRYDSBNDAYTR-UHFFFAOYSA-N
• SMILES: O=C(O)C1=CC=CC=C1CN(CCCCC(O)=O)CCC2=CC=CC=C2OCC3=CC=C(CCC4=CC=CC=C4)C=C3

Cinaciguat, also known as BAY582667 or BAY58-2667, is a soluble guanylate cyclase activator. Cinaciguat prevents cardiac dysfunction in a rat model of type-1 diabetes mellitus. Cinaciguat exert no direct effects on contractility and relaxation of cardiac myocytes from normal rats. Cinaciguat prevents neointima formation after arterial injury by decreasing vascular smooth muscle cell migration and proliferation.

Reference

1:Cinaciguat prevents the development of pathologic hypertrophy in a rat model of left ventricular pressure overload. Németh BT, Mátyás C, Oláh A, Lux Á, Hidi L, Ruppert M, Kellermayer D, Kökény G, Szabó G, Merkely B, Radovits T.Sci Rep. 2016 Nov 17;6:37166. doi: 10.1038/srep37166. PMID: 27853261 Free PMC Article2:The soluble guanylate cyclase activator cinaciguat prevents cardiac dysfunction in a rat model of type-1 diabetes mellitus. Mátyás C, Németh BT, Oláh A, Hidi L, Birtalan E, Kellermayer D, Ruppert M, Korkmaz-Icöz S, Kökény G, Horváth EM, Szabó G, Merkely B, Radovits T.Cardiovasc Diabetol. 2015 Oct 31;14:145. doi: 10.1186/s12933-015-0309-x. PMID: 26520063 Free PMC Article3:The soluble guanylate cyclase stimulator riociguat and the soluble guanylate cyclase activator cinaciguat exert no direct effects on contractility and relaxation of cardiac myocytes from normal rats. Reinke Y, Gross S, Eckerle LG, Hertrich I, Busch M, Busch R, Riad A, Rauch BH, Stasch JP, Dörr M, Felix SB.Eur J Pharmacol. 2015 Nov 15;767:1-9. doi: 10.1016/j.ejphar.2015.09.022. Epub 2015 Sep 25. PMID: 26407652 4:Influence of cinaciguat on gastrointestinal motility in apo-sGC mice. Cosyns SM, Huyghe L, Thoonen R, Stasch JP, Brouckaert P, Lefebvre RA.Neurogastroenterol Motil. 2014 Nov;26(11):1573-85. doi: 10.1111/nmo.12424. Epub 2014 Sep 8. PMID: 25200007 Free Article5:Cinaciguat, a soluble guanylate cyclase activator, unloads the heart but also causes hypotension in acute decompensated heart failure. Erdmann E, Semigran MJ, Nieminen MS, Gheorghiade M, Agrawal R, Mitrovic V, Mebazaa A.Eur Heart J. 2013 Jan;34(1):57-67. doi: 10.1093/eurheartj/ehs196. Epub 2012 Jul 9. PMID: 22778174 6:Cinaciguat, a soluble guanylate cyclase activator: results from the randomized, controlled, phase IIb COMPOSE programme in acute heart failure syndromes. Gheorghiade M, Greene SJ, Filippatos G, Erdmann E, Ferrari R, Levy PD, Maggioni A, Nowack C, Mebazaa A; COMPOSE Investigators and Coordinators..Eur J Heart Fail. 2012 Sep;14(9):1056-66. Epub 2012 Jun 19. PMID: 22713287 Free Article7:Insight into the rescue of oxidized soluble guanylate cyclase by the activator cinaciguat. Surmeli NB, Marletta MA.Chembiochem. 2012 May 7;13(7):977-81. doi: 10.1002/cbic.201100809. Epub 2012 Mar 30. PMID: 22474005 Free PMC Article8:Cinaciguat prevents neointima formation after arterial injury by decreasing vascular smooth muscle cell migration and proliferation. Hirschberg K, Tarcea V, Páli S, Barnucz E, Gwanmesia PN, Korkmaz S, Radovits T, Loganathan S, Merkely B, Karck M, Szabó G.Int J Cardiol. 2013 Jul 31;167(2):470-7. doi: 10.1016/j.ijcard.2012.01.032. Epub 2012 Feb 20. PMID: 22357420 9:Cinaciguat, a novel activator of soluble guanylate cyclase, protects against ischemia/reperfusion injury: role of hydrogen sulfide. Salloum FN, Das A, Samidurai A, Hoke NN, Chau VQ, Ockaili RA, Stasch JP, Kukreja RC.Am J Physiol Heart Circ Physiol. 2012 Mar 15;302(6):H1347-54. doi: 10.1152/ajpheart.00544.2011. Epub 2012 Jan 20. PMID: 22268103 Free PMC Article10:Pharmacokinetics of the soluble guanylate cyclase activator cinaciguat in individuals with hepatic impairment. Frey R, Scheerans C, Blunck M, Mück W, Gnoth MJ, Unger S, Schmidt A, Wensing G.J Clin Pharmacol. 2012 Nov;52(11):1714-24. doi: 10.1177/0091270011426143. Epub 2011 Dec 12. PMID: 22162535