An activator of sGC
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Cinaciguat (hydrochloride)

Item No. 17468

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-[[(4-carboxybutyl)[2-[2-[[4-(2-phenylethyl)phenyl]methoxy]phenyl]ethyl]amino]methyl]-benzoic acid, monohydrochloride
CAS Number
646995-35-9
Synonyms
  • BAY 58-2667
Molecular Formula
C36H39NO5 • HCl
Formula Weight
602.2
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/mlEthanol: 5 mg/ml
λmax
223 nm
SMILES
OC(C(C=C1)=CC=C1CN(CCCCC(O)=O)CCC(C=CC=C2)=C2OCC(C=C3)=CC=C3CCC4=CC=CC=C4)=O.Cl
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $63

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    1 mg

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    5 mg

    $423

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    10 mg

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    Product Description

    Soluble guanylate cyclase (sGC) is the primary cellular receptor for NO. NO binds and activates a heme group in sGC, initiating the conversion of GTP to the second messenger cGMP. cGMP subsequently mediates a number of signaling cascades leading to vasorelaxation and inhibiting smooth muscle proliferation, leukocyte recruitment, and platelet aggregation. Oxidation of the heme results in its dissociation from sGC and an impairment of NO signaling, which has been linked to hypertension, hyperlidemia, cardiovascular disease, and diabetes.1 Cinaciguat is an activator of sGC that binds to a regulatory site, resulting in activation in an NO-independent manner (Kd = 3.2 nM).2 It activates the enzyme even if it has been oxidized or rendered heme deficient.2 In animals, cinaciguat has been shown to reduce hypertension, limit cardiomyocyte hypertrophy, protect against ischemia/reperfusion injury, and reduce morbidity and mortality in response to endotoxic shock.2,3,4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Stasch, J.P., Pacher, P., and Evgenov, O.V. Soluble guanylate cyclase as an emerging therapeutic target in cardiopulmonary disease. Circulation 123(20), 2263-2273 (2011).

    2. Stasch, J.P., Schmidt, P., Alonso-Alija, C., et al. NO- and haem-independent activation of soluble guanylyl cyclase: Molecular basis and cardiovascular implications of a new pharmacological principle. Br. J. Pharmacol. 136(5), 773-783 (2002).

    3. Irvine, J.C., Ganthavee, V., Love, J.E., et al. The soluble guanylyl cyclase activator bay 58-2667 selectively limits cardiomyocyte hypertrophy. PLoS One 7(11), 1-11 (2012).

    4. Salloum, F.N., Das, A., Samidurai, A., et al. Cinaciguat, a novel activator of soluble guanylate cyclase, protects against ischemia/reperfusion injury: role of hydrogen sulfide. Am. J. Physiol. Heart Circ. Physiol. 302(6), H1347-H1354 (2012).

    5. Vandendriessche, B., Rogge, E., Goossens, V., et al. The soluble guanylate cyclase activator BAY 58-2667 protects against morbidity and mortality in endotoxic shock by recoupling organ systems. PLoS One 8(9), 1-10 (2013).