ChemicalBook--->CAS DataBase List--->646995-35-9

646995-35-9

646995-35-9 Structure

646995-35-9 Structure
IdentificationBack Directory
[Name]

BAY 58-2667 hydrochloride
[CAS]

646995-35-9
[Synonyms]

Cinaciguat HCl
Cinaciguat (hydrochloride)
Cinaciguat hydrochloride >=98% (HPLC)
BAY 58-2667 hydrochloride - Cinaciguat hydrochloride
4-[[(4-Carboxybutyl)[2-[2-[[4-(2-phenylethyl)phenyl]methoxy]phenyl]ethyl]amino]methyl]benzoic acid hydrochloride
[Molecular Formula]

C36H40ClNO5
[MDL Number]

MFCD28127267
[MOL File]

646995-35-9.mol
[Molecular Weight]

602.17
Chemical PropertiesBack Directory
[storage temp. ]

-20°C
[solubility ]

DMSO:66.74(Max Conc. mg/mL);110.83(Max Conc. mM)
DMSO:PBS (pH 7.2) (1:1):0.5(Max Conc. mg/mL);0.83(Max Conc. mM)
DMF:30.0(Max Conc. mg/mL);49.82(Max Conc. mM)
Ethanol:5.0(Max Conc. mg/mL);8.3(Max Conc. mM)
[form ]

powder
[color ]

white to beige
[InChIKey]

LLHMBJOVHATVSP-UHFFFAOYSA-N
[SMILES]

OC(C(C=C1)=CC=C1CN(CCCCC(O)=O)CCC2=CC=CC=C2OCC3=CC=C(CCC4=CC=CC=C4)C=C3)=O.[H]Cl
Safety DataBack Directory
[WGK Germany ]

WGK 3
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[Uses]

Cinaciguat hydrochloride is a potent soluble guanylate cyclase (GC) activator with EC50 of 15 nM in platelets.
[Biochem/physiol Actions]

Cinaciguat activates sGC (soluble guanylate cyclase) independently of NO. Cinaciguat binds to sGC′s NO-sensory H-NOX domain when it is heme-depleted. Also, the compound Cinaciguat protects sGC from oxidation-induced ubiquitin-triggered degradation.
[in vivo]

Administration of Cinaciguat decreased BP and increased HR in both apo-sGC mice and WT mice. In fact, the BP-lowering effect of Cinaciguat in apo-sGC mice is significantly greater and longer lasting than in WT mice. In addition, Cinaciguat decreased BP in apo-sGC mice at concentrations that did not affect BP in WT mice. Furthermore, the IC50 values for Cinaciguat-induced ex vivorelaxation of precontracted aortas are threefold lower in apo-sGC mice than in WT mice (IC50=0.2 nM and 0.7 nM, respectively). Together, our results suggest that sGC activators like Cinaciguat but not sGC stimulators like BAY 41-2272 activate apo-sGC. In addition, the observation that Cinaciguat can modulate vasorelaxation and BP in WT mice suggests that even in healthy mice, a subset of the available sGC pool is haem-free and responsive to sGC activators[2].

[storage]

Store at -20°C
[References]

[1] Roy B, et al. Probing the presence of the ligand-binding haem in cellular nitric oxide receptors. Br J Pharmacol. 2008 Apr;153(7):1495-504. DOI:10.1038/sj.bjp.0707687
[2] Thoonen R, et al. Cardiovascular and pharmacological implications of haem-deficient NO-unresponsive soluble guanylate cyclase knock-in mice. Nat Commun. 2015 Oct 7;6:8482. DOI:10.1038/ncomms9482
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