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MedKoo Cat#: 412907 | Name: Cinaciguat
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Description:

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

Cinaciguat is an experimental drug for the treatment of acute decompensated heart failure. It activates guanylyl cyclase.

Chemical Structure

Cinaciguat
Cinaciguat
CAS#329773-35-5 (free)

Theoretical Analysis

MedKoo Cat#: 412907

Name: Cinaciguat

CAS#: 329773-35-5 (free)

Chemical Formula: C36H39NO5

Exact Mass: 565.2828

Molecular Weight: 565.71

Elemental Analysis: C, 76.43; H, 6.95; N, 2.48; O, 14.14

Price and Availability

Size Price Availability Quantity
5mg USD 450.00 2 Weeks
10mg USD 800.00 2 Weeks
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Related CAS #
646995-35-9 (HCl) 329773-35-5 (free)
Synonym
Cinaciguat; BAY 58-2667; BAY 582667; BAY 58 2667
IUPAC/Chemical Name
4-(((4-carboxybutyl)(2-((4-phenethylbenzyl)oxy)phenethyl)amino)methyl)benzoic acid
InChi Key
WPYWMXNXEZFMAK-UHFFFAOYSA-N
InChi Code
InChI=1S/C36H39NO5/c38-35(39)12-6-7-24-37(26-30-19-21-33(22-20-30)36(40)41)25-23-32-10-4-5-11-34(32)42-27-31-17-15-29(16-18-31)14-13-28-8-2-1-3-9-28/h1-5,8-11,15-22H,6-7,12-14,23-27H2,(H,38,39)(H,40,41)
SMILES Code
O=C(O)C1=CC=C(CN(CCCCC(O)=O)CCC2=CC=CC=C2OCC3=CC=C(CCC4=CC=CC=C4)C=C3)C=C1
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
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

Preparing Stock Solutions

The following data is based on the product molecular weight 565.71 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: Jia T, Wang YN, Zhang J, Hao X, Zhang D, Xu X. Cinaciguat in combination with insulin induces a favorable effect on implant osseointegration in type 2 diabetic rats. Biomed Pharmacother. 2019 Oct;118:109216. doi: 10.1016/j.biopha.2019.109216. Epub 2019 Jul 15. PMID: 31319371. 2: Czirok S, Fang L, Radovits T, Szabó G, Szénási G, Rosivall L, Merkely B, Kökény G. Cinaciguat ameliorates glomerular damage by reducing ERK1/2 activity and TGF-ß expression in type-1 diabetic rats. Sci Rep. 2017 Sep 11;7(1):11218. doi: 10.1038/s41598-017-10125-3. PMID: 28894114; PMCID: PMC5593847. 3: Cosyns SM, Huyghe L, Thoonen R, Stasch JP, Brouckaert P, Lefebvre RA. Influence of cinaciguat on gastrointestinal motility in apo-sGC mice. Neurogastroenterol Motil. 2014 Nov;26(11):1573-85. doi: 10.1111/nmo.12424. Epub 2014 Sep 8. PMID: 25200007. 4: Salloum FN, Das A, Samidurai A, Hoke NN, Chau VQ, Ockaili RA, Stasch JP, Kukreja RC. Cinaciguat, a novel activator of soluble guanylate cyclase, protects against ischemia/reperfusion injury: role of hydrogen sulfide. 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; PMCID: PMC3311478. 5: Chester M, Seedorf G, Tourneux P, Gien J, Tseng N, Grover T, Wright J, Stasch JP, Abman SH. Cinaciguat, a soluble guanylate cyclase activator, augments cGMP after oxidative stress and causes pulmonary vasodilation in neonatal pulmonary hypertension. Am J Physiol Lung Cell Mol Physiol. 2011 Nov;301(5):L755-64. doi: 10.1152/ajplung.00138.2010. Epub 2011 Aug 19. PMID: 21856817; PMCID: PMC3213988. 6: Kollau A, Opelt M, Wölkart G, Gorren ACF, Russwurm M, Koesling D, Mayer B, Schrammel A. Irreversible Activation and Stabilization of Soluble Guanylate Cyclase by the Protoporphyrin IX Mimetic Cinaciguat. Mol Pharmacol. 2018 Feb;93(2):73-78. doi: 10.1124/mol.117.109918. Epub 2017 Nov 14. PMID: 29138269; PMCID: PMC5916872. 7: Lapp H, Mitrovic V, Franz N, Heuer H, Buerke M, Wolfertz J, Mueck W, Unger S, Wensing G, Frey R. Cinaciguat (BAY 58-2667) improves cardiopulmonary hemodynamics in patients with acute decompensated heart failure. Circulation. 2009 Jun 2;119(21):2781-8. doi: 10.1161/CIRCULATIONAHA.108.800292. Epub 2009 May 18. PMID: 19451356. 8: Gheorghiade M, Greene SJ, Filippatos G, Erdmann E, Ferrari R, Levy PD, Maggioni A, Nowack C, Mebazaa A; COMPOSE Investigators and Coordinators. Cinaciguat, a soluble guanylate cyclase activator: results from the randomized, controlled, phase IIb COMPOSE programme in acute heart failure syndromes. Eur J Heart Fail. 2012 Sep;14(9):1056-66. doi: 10.1093/eurjhf/hfs093. Epub 2012 Jun 19. PMID: 22713287. 9: Breitenstein S, Roessig L, Sandner P, Lewis KS. Novel sGC Stimulators and sGC Activators for the Treatment of Heart Failure. Handb Exp Pharmacol. 2017;243:225-247. doi: 10.1007/164_2016_100. PMID: 27900610. 10: Erdmann E, Semigran MJ, Nieminen MS, Gheorghiade M, Agrawal R, Mitrovic V, Mebazaa A. Cinaciguat, a soluble guanylate cyclase activator, unloads the heart but also causes hypotension in acute decompensated heart failure. Eur Heart J. 2013 Jan;34(1):57-67. doi: 10.1093/eurheartj/ehs196. Epub 2012 Jul 9. PMID: 22778174.