196876

BAY 41-2272

A cell-permeable pyrazolopyridinylpyrimidine compound that acts as a selective and potent stimulator of soluble guanylate cyclase (effective dose ~ 0.1 nM to 100 µM using recombinant soluble guanylate cyclase).

• Synonym(s): BAY 41-2272, 5-Cyclopropyl-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-4-ylamine
• Empirical Formula (Hill Notation): C₂₀H₁₇FN₆
• CAS Number: 256376-24-6
• Molecular Weight: 360.39
• MDL number: MFCD06411391
• UNSPSC Code: 51111800
• NACRES: NA.77
• Assay: ≥98% (HPLC)
• Form: solid
• Quality level: 100
• Storage condition: OK to freeze, protect from light

Properties

• Quality Level: 100
• assay: ≥98% (HPLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze, protect from light
• color: white
• solubility: DMSO: 10 mg/mL
• shipped in: ambient
• storage temp.: 2-8°C
• SMILES string: Fc1c(cccc1)C[n]2nc(c5c2nccc5)c3nc(c(cn3)C4CC4)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)
• InChI key: ATOAHNRJAXSBOR-UHFFFAOYSA-N

Description

General description

A cell-permeable pyrazolopyridinylpyrimidine compound that acts as a selective and potent stimulator of soluble guanylate cyclase (effective dose ~ 0.1 nM to 100 µM using recombinant soluble guanylate cyclase). The mode of activation is NO-independent and appears to be mediated through direct binding to the α₁ and α₂ subunits. Shown to be effective in treating numerous cardiovascular conditions in animal models. Inhibits phenylephrine-induced constriction of rabbit aortic rings (IC₅₀ = 304 nM) and blocks collagen-induced aggregation of human platelets (IC₅₀ = 36 nM). Does not inhibit phosphodiesterases.

Biochem/physiol Actions

Cell permeable: yes

Primary Target
Soluble guanylate cyclase

Product does not compete with ATP.

Reversible: no

Target IC₅₀: 304 nM inhibiting phenylephrine-induced constriction of rabbit aortic rings; 36 nM in blocking collagen-induced aggregation of human platelets

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Boerrigter, G., et al. 2003. Circulation107, 686.
Kalsi, J.S., et al. 2003. J Urol.169, 761.
Koglin, M., et al. 2002. Biochem. Biophys. Res. Commun.292, 1057.
Becker, E.M., et al. 2001. BMC Pharmacol.1, 13.
Stasch, J.P., et al. 2001. Nature410, 212.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable