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Merck
CN

SML2311

BAY 60-7550

≥95% (HPLC)

Synonym(s):

2-(3,4-Dimethoxybenzyl)-7-{(1R)-1-[(1R)-1-hydroxyethyl]-4-phenylbutyl}-5-methyllimidazo[5,1-f][1,2,4]triazin-4(3H)-one, BAY-60−7550, BAY60-7550

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About This Item

Empirical Formula (Hill Notation):
C27H32N4O4
CAS Number:
439083-90-6
Molecular Weight:
476.57
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD08702694

Key Documents

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Product Name

BAY 60-7550, ≥95% (HPLC)

SMILES string

[n]21[nH]c(n[c](c2c(nc1[C@H]([C@H](O)C)CCCc4ccccc4)C)=O)Cc3cc(c(cc3)OC)OC

InChI

1S/C27H32N4O4/c1-17-25-27(33)29-24(16-20-13-14-22(34-3)23(15-20)35-4)30-31(25)26(28-17)21(18(2)32)12-8-11-19-9-6-5-7-10-19/h5-7,9-10,13-15,18,21,32H,8,11-12,16H2,1-4H3,(H,29,30,33)/t18-,21+/m1/s1

InChI key

MYTWFJKBZGMYCS-NQIIRXRSSA-N

assay

≥95% (HPLC)

form

powder

color

white to light brown

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

Related Categories

Biochem/physiol Actions

BAY 60-7550 is an orally active, potent and selective cGMP-dependent phosphodiesterase PDE2 (PDE2A) inhibitor (human/bovine PDE2 IC50 = 4.7/2.0 nM; bovine PDE1 IC50 = 108 nM, human PDE5/5A/10A/4B IC50 = 240/580/704/940/1830 nM, human PDE3B/7B/8A/9A/11A IC50 >4 μM) with little activity (IC50 >10 μM) toward acetylcholinesterase, mAO-A/B, adenosine deaminase, and many receptor subtypes tested. Bay 60-7550 effectively upregulates cGMP and cAMP level in cultured rat and murine neurons (1 nM-1 μM) exposed to guanylyl cyclase (GC) or adenylyl cyclase (AC) stimulator (1 μM Bay 41-8543 or 2 μM forskolin), respectively, as well as exhibits learning and memory-improving efficacy in rats (0.6-3 mg/kg p.o.) and mice (0.3-1 mg/kg p.o.) in vivo.
Orally active, potent and selective cGMP-dependent phosphodiesterase PDE2 (PDE2A) inhibitor with learning and memory-improving efficacy in vivo.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000477403
0000477403
0000425339
0000425339
0000220584

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Stefania Monterisi et al.
eLife, 6 (2017-05-04)
cAMP/PKA signalling is compartmentalised with tight spatial and temporal control of signal propagation underpinning specificity of response. The cAMP-degrading enzymes, phosphodiesterases (PDEs), localise to specific subcellular domains within which they control local cAMP levels and are key regulators of signal
Remi Neviere et al.
International journal of molecular sciences, 17(12) (2016-12-16)
Adrenergic receptors couple to Gs-proteins leading to transmembrane adenylyl cyclase activation and cytosolic cyclic adenosine monophosphate (cAMP) production. Cyclic AMP is also produced in the mitochondrial matrix, where it regulates respiration through protein kinase A (PKA)-dependent phosphorylation of respiratory chain
Ligia Mendes Soares et al.
The European journal of neuroscience, 45(4), 510-520 (2016-11-05)
Cognitive and affective impairments are the most characterized consequences following cerebral ischemia. BAY 60-7550, a selective phosphodiesterase type 2 inhibitor (PDE2-I), presents memory-enhancing and anxiolytic-like properties. The behavioral effects of BAY 60-7550 have been associated with its ability to prevent
Christiane Vettel et al.
Circulation research, 120(1), 120-132 (2016-11-02)
Phosphodiesterase 2 is a dual substrate esterase, which has the unique property to be stimulated by cGMP, but primarily hydrolyzes cAMP. Myocardial phosphodiesterase 2 is upregulated in human heart failure, but its role in the heart is unknown. To explore
Wen Chen et al.
Circulation research, 119(2), 237-248 (2016-05-05)
In patients after acute myocardial infarction (AMI), the initial extent of necrosis and inflammation determine clinical outcome. One early event in AMI is the increased cardiac expression of atrial natriuretic peptide (NP) and B-type NP, with their plasma levels correlating
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