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MedKoo Cat#: 319904 | Name: Cinaciguat HCl
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Description:

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

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.

Chemical Structure

Cinaciguat HCl
Cinaciguat HCl
CAS#646995-35-9 (HCl)

Theoretical Analysis

MedKoo Cat#: 319904

Name: Cinaciguat HCl

CAS#: 646995-35-9 (HCl)

Chemical Formula: C36H40ClNO5

Exact Mass: 565.2828

Molecular Weight: 602.17

Elemental Analysis: C, 71.81; H, 6.70; Cl, 5.89; N, 2.33; O, 13.28

Price and Availability

Size Price Availability Quantity
50mg USD 650.00 2 Weeks
100mg USD 950.00 2 Weeks
200mg USD 1,450.00 2 Weeks
500mg USD 2,650.00 2 Weeks
1g USD 3,650.00 2 Weeks
2g USD 6,450.00 2 Weeks
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Related CAS #
646995-35-9 (HCl) 329773-35-5 (free)
Synonym
BAY 582667; BAY-582667; BAY582667; BAY 58-2667; BAY-58-2667; BAY58-2667; Cinaciguat; Cinaciguat HCl; Cinaciguat hydrochloride;
IUPAC/Chemical Name
2-(((4-carboxybutyl)(2-((4-phenethylbenzyl)oxy)phenethyl)amino)methyl)benzoic acid hydrochloride
InChi Key
LSXMCAMGQOJSBO-UHFFFAOYSA-N
InChi Code
InChI=1S/C36H39NO5.ClH/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);1H
SMILES Code
O=C(O)C1=CC=CC=C1CN(CCCCC(O)=O)CCC2=CC=CC=C2OCC3=CC=C(CCC4=CC=CC=C4)C=C3.[H]Cl
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 CAS# 646995-35-9 (Cinaciguat hydrochloride) 329773-35-5 (Cinaciguat free)
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Cinaciguat hydrochloride is a potent soluble guanylate cyclase (GC) activator with EC50 of 15 nM in platelets.
In vitro activity:
In vitro wound healing assay with VSMCs revealed dose-dependent antimigratory and antiproliferative effects of cinaciguat. Reference: Int J Cardiol. 2013 Jul 31;167(2):470-7. https://pubmed.ncbi.nlm.nih.gov/22357420/
In vivo activity:
The diabetic eNOS KO mice developed most characteristics of diabetic nephropathy, most marked at 12 weeks. Treatment with cinaciguat markedly improved GFR, serum creatinine, mesangial expansion and kidney fibrosis in these animals. Reference: Br J Pharmacol. 2021 Mar 2. https://pubmed.ncbi.nlm.nih.gov/33651375/
Solvent mg/mL mM comments
Solubility
DMSO 66.7 110.83
DMSO:PBS (pH 7.2) (1:1) 0.5 0.83
DMF 30.0 49.82
Ethanol 5.0 8.30
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 602.17 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
Formulation protocol:
1. Hirschberg K, Tarcea V, Páli S, Barnucz E, Gwanmesia PN, Korkmaz S, Radovits T, Loganathan S, Merkely B, Karck M, Szabó G. Cinaciguat prevents neointima formation after arterial injury by decreasing vascular smooth muscle cell migration and proliferation. Int J Cardiol. 2013 Jul 31;167(2):470-7. doi: 10.1016/j.ijcard.2012.01.032. Epub 2012 Feb 20. PMID: 22357420. 2. Harloff M, Prüschenk S, Seifert R, Schlossmann J. Activation of soluble guanylyl cyclase signalling with cinaciguat improves impaired kidney function in diabetic mice. Br J Pharmacol. 2021 Mar 2. doi: 10.1111/bph.15425. Epub ahead of print. PMID: 33651375. 3. 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.
In vitro protocol:
1. Hirschberg K, Tarcea V, Páli S, Barnucz E, Gwanmesia PN, Korkmaz S, Radovits T, Loganathan S, Merkely B, Karck M, Szabó G. Cinaciguat prevents neointima formation after arterial injury by decreasing vascular smooth muscle cell migration and proliferation. Int J Cardiol. 2013 Jul 31;167(2):470-7. doi: 10.1016/j.ijcard.2012.01.032. Epub 2012 Feb 20. PMID: 22357420.
In vivo protocol:
1. Harloff M, Prüschenk S, Seifert R, Schlossmann J. Activation of soluble guanylyl cyclase signalling with cinaciguat improves impaired kidney function in diabetic mice. Br J Pharmacol. 2021 Mar 2. doi: 10.1111/bph.15425. Epub ahead of print. PMID: 33651375. 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.
1: Hung YC, Liu YC, Wu BN, Yeh JL, Hsu JH. Cinaciguat Prevents Postnatal Closure of Ductus Arteriosus by Vasodilation and Anti-remodeling in Neonatal Rats. Front Physiol. 2021 Jul 29;12:661171. doi: 10.3389/fphys.2021.661171. PMID: 34393808; PMCID: PMC8358454. 2: Lombardi CM, Cimino G, Pagnesi M, Dell'Aquila A, Tomasoni D, Ravera A, Inciardi R, Carubelli V, Vizzardi E, Nodari S, Emdin M, Aimo A. Vericiguat for Heart Failure with Reduced Ejection Fraction. Curr Cardiol Rep. 2021 Aug 19;23(10):144. doi: 10.1007/s11886-021-01580-6. PMID: 34410527; PMCID: PMC8376697. 3: Beñaldo FA, Araya-Quijada C, Ebensperger G, Herrera EA, Reyes RV, Moraga FA, Riquelme A, Gónzalez-Candia A, Castillo-Galán S, Valenzuela GJ, Serón-Ferré M, Llanos AJ. Cinaciguat (BAY-582667) Modifies Cardiopulmonary and Systemic Circulation in Chronically Hypoxic and Pulmonary Hypertensive Neonatal Lambs in the Alto Andino. Front Physiol. 2022 Jun 6;13:864010. doi: 10.3389/fphys.2022.864010. PMID: 35733986; PMCID: PMC9207417. 4: 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. 5: 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. 6: 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. 7: Hirschberg K, Tarcea V, Páli S, Barnucz E, Gwanmesia PN, Korkmaz S, Radovits T, Loganathan S, Merkely B, Karck M, Szabó G. Cinaciguat prevents neointima formation after arterial injury by decreasing vascular smooth muscle cell migration and proliferation. Int J Cardiol. 2013 Jul 31;167(2):470-7. doi: 10.1016/j.ijcard.2012.01.032. Epub 2012 Feb 20. PMID: 22357420. 8: 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. 9: 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. 10: 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. 11: Hingorany S, Frishman WH. Soluble guanylate cyclase activation with cinaciguat: a new approach to the treatment of decompensated heart failure. Cardiol Rev. 2011 Jan-Feb;19(1):23-9. doi: 10.1097/CRD.0b013e3181fc1c10. PMID: 21135599. 12: 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. 13: Chester M, Tourneux P, Seedorf G, Grover TR, Gien J, Abman SH. Cinaciguat, a soluble guanylate cyclase activator, causes potent and sustained pulmonary vasodilation in the ovine fetus. Am J Physiol Lung Cell Mol Physiol. 2009 Aug;297(2):L318-25. doi: 10.1152/ajplung.00062.2009. Epub 2009 May 22. PMID: 19465519; PMCID: PMC2742799. 14: 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. 15: Jia A, Jiang H, Liu W, Chen P, Xu Q, Zhang R, Sun J. Novel application potential of cinaciguat in the treatment of mixed hyperlipidemia through targeting PTL/NPC1L1 and alleviating intestinal microbiota dysbiosis and metabolic disorders. Pharmacol Res. 2023 Jul 17;194:106854. doi: 10.1016/j.phrs.2023.106854. Epub ahead of print. PMID: 37460003. 16: Harloff M, Prüschenk S, Seifert R, Schlossmann J. Activation of soluble guanylyl cyclase signalling with cinaciguat improves impaired kidney function in diabetic mice. Br J Pharmacol. 2022 Jun;179(11):2460-2475. doi: 10.1111/bph.15425. Epub 2021 May 4. PMID: 33651375. 17: Németh BT, Mátyás C, Oláh A, Lux Á, Hidi L, Ruppert M, Kellermayer D, Kökény G, Szabó G, Merkely B, Radovits T. Cinaciguat prevents the development of pathologic hypertrophy in a rat model of left ventricular pressure overload. Sci Rep. 2016 Nov 17;6:37166. doi: 10.1038/srep37166. PMID: 27853261; PMCID: PMC5112572. 18: Laubrie JD, Bezmalinovic A, García-Herrera CM, Celentano DJ, Herrera EA, Avril S, Llanos AJ. Hyperelastic and damage properties of the hypoxic aorta treated with Cinaciguat. J Biomech. 2023 Jan;147:111457. doi: 10.1016/j.jbiomech.2023.111457. Epub 2023 Jan 16. PMID: 36701962. 19: Frey R, Scheerans C, Blunck M, Mück W, Gnoth MJ, Unger S, Schmidt A, Wensing G. Pharmacokinetics of the soluble guanylate cyclase activator cinaciguat in individuals with hepatic impairment. J Clin Pharmacol. 2012 Nov;52(11):1714-24. doi: 10.1177/0091270011426143. Epub 2011 Dec 12. PMID: 22162535. 20: Aimo A, Castiglione V, Vergaro G, Panichella G, Senni M, Lombardi CM, Emdin M. The place of vericiguat in the landscape of treatment for heart failure with reduced ejection fraction. Heart Fail Rev. 2022 Jul;27(4):1165-1171. doi: 10.1007/s10741-021-10146-1. Epub 2021 Jul 21. PMID: 34291399; PMCID: PMC9197896.