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SML1532

Sigma-Aldrich

Cinaciguat hydrochloride

≥98% (HPLC)

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Synonym(s):
4-[((4-Carboxybutyl){2-[(4-phenethylbenzyl)oxy]phenethyl}amino)methyl[benzoic]acid hydrochloride, 4-[[(4-Carboxybutyl)[2-[2-[[4-(2-phenylethyl)phenyl]methoxy]phenyl]ethyl]amino]methyl]-benzoic acid hydrochloride, BAY 58-2667 hydrochloride, BAY582667 hydrochloride, UNII-59K0Y58UAD hydrochloride
Empirical Formula (Hill Notation):
C36H39NO5 · HCl
CAS Number:
646995-35-9
Molecular Weight:
602.16
MDL number:
MFCD28127267
UNSPSC Code:
12352200
PubChem Substance ID:
329825948
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 10 mg/mL, clear

storage temp.

−20°C

SMILES string

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

InChI

1S/C36H39NO5.ClH/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);1H

InChI key

LLHMBJOVHATVSP-UHFFFAOYSA-N

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.
Cinaciguat, also known as BAY 58-2667, is a novel activator of guanylate cyclase. It is used in the treatment of acute decompensated heart failure (ADHF). It has been reported that cinaciguat possesses cardiovascular effects.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Wolfgang Mueck et al.
Clinical pharmacokinetics, 49(2), 119-129 (2010-01-14)
Cinaciguat (BAY 58-2667) is a novel soluble guanylate cyclase activator in clinical development for the treatment of acute decompensated heart failure (ADHF). In patients with ADHF, intravenously administered cinaciguat results in potent unloading of the heart with arterial vasodilation. The

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