Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C20H17FN6 |
| Molecular Weight | 360.3876 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC(=NC=C1C2CC2)C3=NN(CC4=CC=CC=C4F)C5=NC=CC=C35
InChI
InChIKey=ATOAHNRJAXSBOR-UHFFFAOYSA-N
InChI=1S/C20H17FN6/c21-16-6-2-1-4-13(16)11-27-20-14(5-3-9-23-20)17(26-27)19-24-10-15(12-7-8-12)18(22)25-19/h1-6,9-10,12H,7-8,11H2,(H2,22,24,25)
BAY-41-2272 is a direct and NO-independent soluble guanylate cyclase (sGC) stimulator. It sensitizes sGC to nitric oxide (NO), its physiological stimulator, and contains antiplatelet activity. BAY-41-2272 is an inhibitor of GCS. BAY-41-2272 inhibits platelet aggregation (IC50 = 36 nM) and phenylephrine-induced contractions of rabbit aorta (IC50 = 0.30 uM). BAY-41-2272 also reduces vascular smooth muscle growth through cAMP- and cGMP-dependent PKA and PKG pathways. BAY-41-2272 not only sensitized NO-sensitive GC toward activation by NO but also, with comparable potency, inhibited cGMP degradation by PDE5. BAY-41-2272 may provide a novel therapeutic compound for treating chronic hypoxic pulmonary hypertension.
Originator
Sources: http://adisinsight.springer.com/drugs/800016537 | https://www.ncbi.nlm.nih.gov/pubmed/19263460
Curator's Comment: # Bayer
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Andrographolide inhibits tumor angiogenesis via blocking VEGFA/VEGFR2-MAPKs signaling cascade. | 2014-07-25 |
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| BAY 41-2272 inhibits the development of chronic hypoxic pulmonary hypertension in rats. | 2010-11-25 |
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| The anti-aggregating effect of BAY 41-2272, a stimulator of soluble guanylyl cyclase, requires the presence of nitric oxide. | 2010-11 |
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| Mechanisms of relaxant activity of the nitric oxide-independent soluble guanylyl cyclase stimulator BAY 41-2272 in rat tracheal smooth muscle. | 2010-10-25 |
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| Heme oxygenase-1 deficiency leads to alteration of soluble guanylate cyclase redox regulation. | 2010-10 |
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| Investigation of relaxant effects of new agents affecting nitric oxide/cyclic guanosine monophosphate pathway on sheep oddi sphincter. | 2010-08 |
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| Evaluation of the relaxant effect of the nitric oxide-independent soluble guanylyl cyclase stimulator BAY 41-2272 in isolated detrusor smooth muscle. | 2010-07-10 |
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| Binding of YC-1/BAY 41-2272 to soluble guanylate cyclase: A new perspective to the mechanism of activation. | 2010-07-02 |
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| Effects of sex and estrogen on chicken ductus arteriosus reactivity. | 2010-05 |
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| Nitric oxide stimulates interleukin-6 production in skeletal myotubes. | 2010-05 |
|
| Role of soluble guanylyl cyclase-cyclic GMP signaling in tumor cell proliferation. | 2010-01-01 |
|
| Pharmacological stimulation of soluble guanylate cyclase modulates hypoxia-inducible factor-1alpha in rat heart. | 2009-10 |
|
| Soluble guanylate cyclase agonists inhibit expression and procoagulant activity of tissue factor. | 2009-10 |
|
| Distinct molecular requirements for activation or stabilization of soluble guanylyl cyclase upon haem oxidation-induced degradation. | 2009-07 |
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| Pressure-independent effects of pharmacological stimulation of soluble guanylate cyclase on fibrosis in pressure-overloaded rat heart. | 2009-07 |
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| Nitrite or sildenafil, but not BAY 41-2272, blunt acute pulmonary embolism-induced increases in circulating matrix metalloproteinase-9 and oxidative stress. | 2009-07 |
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| Soluble guanylate cyclase: not a dull enzyme. | 2009-06-02 |
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| NO-independent activators of soluble guanylate cyclase: therapeutic potential. | 2009-05 |
|
| Discovery of riociguat (BAY 63-2521): a potent, oral stimulator of soluble guanylate cyclase for the treatment of pulmonary hypertension. | 2009-05 |
|
| Oxidative stress impairs vasorelaxation induced by the soluble guanylyl cyclase activator BAY 41-2272 in spontaneously hypertensive rats. | 2009-05 |
|
| Novel soluble guanylyl cyclase stimulator BAY 41-2272 attenuates ischemia-reperfusion-induced lung injury. | 2009-03 |
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| Antigrowth properties of BAY 41-2272 in vascular smooth muscle cells. | 2009-02 |
|
| Novel therapies for cyclic GMP control of vascular smooth muscle growth. | 2009-01-08 |
|
| Activation of BKCa channels by nitric oxide prevents coronary artery endothelial dysfunction in ouabain-induced hypertensive rats. | 2009-01 |
|
| YC-1 stimulates the expression of gaseous monoxide-generating enzymes in vascular smooth muscle cells. | 2009-01 |
|
| Binding of YC-1 or BAY 41-2272 to soluble guanylyl cyclase induces a geminate phase in CO photolysis. | 2008-11-26 |
|
| Increased cyclic guanosine monophosphate synthesis and calcium entry blockade account for the relaxant activity of the nitric oxide-independent soluble guanylyl cyclase stimulator BAY 41-2272 in the rabbit penile urethra. | 2008-09 |
|
| An enzyme-linked receptor mechanism for nitric oxide-activated guanylyl cyclase. | 2008-07-04 |
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| Gender-specific hypertension and responsiveness to nitric oxide in sGCalpha1 knockout mice. | 2008-07-01 |
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| Endothelium removal augments endothelium-independent vasodilatation in rat mesenteric vascular bed. | 2008-05 |
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| Dose-dependent beneficial hemodynamic effects of BAY 41-2272 in a canine model of acute pulmonary thromboembolism. | 2008-02-26 |
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| Gastric motility in soluble guanylate cyclase alpha 1 knock-out mice. | 2007-11-01 |
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| Functional role of the soluble guanylyl cyclase alpha(1) subunit in vascular smooth muscle relaxation. | 2007-10-01 |
|
| Effects of 5-cyclopropyl-2-[1-(2-fluoro-benzyl)-1H-pyrazolo[3,4-b]pyridine-3-yl]pyrimidin-4-ylamine (BAY 41-2272) on smooth muscle tone, soluble guanylyl cyclase activity, and NADPH oxidase activity/expression in corpus cavernosum from wild-type, neuronal, and endothelial nitric-oxide synthase null mice. | 2007-09 |
|
| Effects of BAY 41-2272, an activator of nitric oxide-independent site of soluble guanylate cyclase, on human NADPH oxidase system from THP-1 cells. | 2007-07-12 |
|
| A cell-based nitric oxide reporter assay useful for the identification and characterization of modulators of the nitric oxide/guanosine 3',5'-cyclic monophosphate pathway. | 2007-04-15 |
|
| Differential sensitivity of excitatory and inhibitory synaptic transmission to modulation by nitric oxide in rat nucleus tractus solitarii. | 2007-03 |
|
| Effect of BAY 41-2272 in the pulmonary hypertension induced by heparin-protamine complex in anaesthetized dogs. | 2007-01-05 |
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| Elevated pressure selectively blunts flow-evoked vasodilatation in rat mesenteric small arteries. | 2007-01 |
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| Nitric oxide-independent stimulation of soluble guanylate cyclase with BAY 41-2272 in cardiovascular disease. | 2007 |
|
| Soluble guanylate cyclase stimulation on cardiovascular remodeling in angiotensin II-induced hypertensive rats. | 2006-11 |
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| Soluble guanylyl cyclase activation promotes angiogenesis. | 2006-11 |
|
| Protective effect of prior physical conditioning on relaxing response of corpus cavernosum from rats made hypertensive by nitric oxide inhibition. | 2006-08-18 |
|
| Hydrogen peroxide restrains endothelium-derived nitric oxide bioactivity -- role for iron-dependent oxidative stress. | 2006-08-15 |
|
| Protective effects of BAY 41-2272 (sGC stimulator) on hypertension, heart, and cardiomyocyte hypertrophy induced by chronic L-NAME treatment in rats. | 2006-03 |
|
| Vasorelaxing effect of BAY 41-2272 in rat basilar artery: involvement of cGMP-dependent and independent mechanisms. | 2006-03 |
|
| Activation of soluble guanylate cyclase reverses experimental pulmonary hypertension and vascular remodeling. | 2006-01-17 |
|
| Stimulation of soluble guanylyl cyclase by BAY 41-2272 relaxes anococcygeus muscle: interaction with nitric oxide. | 2006-01-13 |
|
| BAY 41-2272, a direct activator of soluble guanylate cyclase, reduces right ventricular hypertrophy and prevents pulmonary vascular remodeling during chronic hypoxia in neonatal rats. | 2006 |
|
| BAY 41-2272, a potent activator of soluble guanylyl cyclase, stimulates calcium elevation and calcium-activated potassium current in pituitary GH cells. | 2005-12 |
Sample Use Guides
Rats: Eight-week-old male Wistar rats with hypertension induced by angiotensin II infused subcutaneously at 250 ng/kg per minute were treated orally with a low ([L] 2 mg/kg per day) or high ([H] 10 mg/kg per day) dose of BAY-41-2272 for 14 days. BAY-41-2272-H partially suppressed the rise in blood pressure and reduced the heart weight (4.20+/-0.34 versus 3.68+/-0.20 mg/g; P<0.01), whereas BAY-41-2272-L had no effect.
Route of Administration:
Oral
In vitro, BAY-41-2272 results in concentration dependent relaxation of human and rabbit cavernosum with EC50 of 489.1 nM and 406.3 nM, respectively. BAY-41-2272 at subthreshold concentrations of 30 to 50 nM potentiated nitrergic responses. Moreover, the inhibition of nitrergic responses by L-NAME was reversed by 0.3 to 3 uM BAY-41-2272.
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DTXSID90180320
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256376-24-6
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ACTIVE MOIETY
