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Merck
CN

B3561

BAY 73-6691

≥98% (HPLC), powder

Synonym(s):

1-(2-Chlorophenyl)-6-[(2R)-3,3,3-trifluoro-2-methylpropyl]-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidine-4-one

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About This Item

Empirical Formula (Hill Notation):
C15H12ClF3N4O
CAS Number:
794568-92-6
Molecular Weight:
356.73
NACRES:
NA.77
PubChem Substance ID:
24724419
UNSPSC Code:
41106305
MDL number:
MFCD08705319

Key Documents

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storage temp.

2-8°C

Quality Level

100

InChI key

FFPXPXOAFQCNBS-MRVPVSSYSA-N

SMILES string

C[C@H](CC1=Nc2c(cnn2-c3ccccc3Cl)C(=O)N1)C(F)(F)F

InChI

1S/C15H12ClF3N4O/c1-8(15(17,18)19)6-12-21-13-9(14(24)22-12)7-20-23(13)11-5-3-2-4-10(11)16/h2-5,7-8H,6H2,1H3,(H,21,22,24)/t8-/m1/s1

assay

≥98% (HPLC)

form

powder

color

off-white

solubility

DMSO: >20 mg/mL

originator

Bayer

Related Categories

Application

BAY 73-6691 has been used as a phosphodiesterase 9 inhibitor in ischemic heart samples and in structural studies. It may be used as a PDE 9 inhibitor in neuroblastoma SH-SY5Y cells.

Biochem/physiol Actions

BAY 73-6691 is the first potent, selective, cell permeable inhibitor of phosphodiesterase 9 (IC50 for human PDE9 = 55 nM; little to no activity at other PDEs); PDE9 is highly selective for cGMP and is detected in brain, kidney, spleen, prostate, colon, and intestine.
BAY 73-6691 was characterized in vitro as the first potent and selective inhibitor of phosphodiesterase 9 (PDE9), which is currently under preclinical development for the treatment of Alzheimer′s disease. This compound selectively inhibits human (IC50 = 55 nM) and murine (IC50 = 100 nM) PDE9 activity in vitro and shows only moderate activity against other cyclic nucleotide-specific phosphodiesterases. BAY 73-6691 alone did not significantly increase basal cGMP levels. The PDE9 inhibitor significantly potentiated the cGMP signals generated by sGC activating compounds such as BAY 58-2667 or 5-cyclopropyl-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-4-ylamine (BAY 41-2272) and induced leftward shifts of the corresponding concentration-response curves. The newly generated PDE9 reporter cell line show that BAY 73-6691 is able to efficiently penetrate cells and to inhibit intracellular PDE9 activity.†

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Phosphodiesterases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Bayer. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 2 Oral - Aquatic Chronic 4 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
0000211710
0000211711
0000211710
0000211711
089K4608V

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Protective effects of BAY 73-6691, a selective inhibitor of phosphodiesterase 9, on amyloid-beta peptides-induced oxidative stress in in-vivo and in-vitro models of Alzheimer's disease
Li J, et al.
Brain Research, 1642, 327-335 (2016)
Insight into binding of phosphodiesterase-9A selective inhibitors by crystal structures and mutagenesis
Wang H, et al.
Journal of Medicinal Chemistry, 53(4), 1726-1731 (2010)
Maritza Cavalcante Barbosa et al.
Basic & clinical pharmacology & toxicology, 118(4), 271-278 (2015-09-09)
The aim of the study was to investigate the possible anti-inflammatory and antioxidant effects of BAY 73-6691 on neutrophils from SCA patients. This study included 35 patients with a molecular diagnosis of SCA, whose neutrophils were isolated and treated with
sGC-cGMP-PKG pathway stimulation protects the healthy but not the failing right ventricle of rats against ischemia and reperfusion injury
Andersen A, et al.
International Journal of Cardiology, 223, 674-680 (2016)
Dewi Safitri et al.
Biochemical pharmacology, 174, 113823-113823 (2020-01-29)
Supressed levels of intracellular cAMP have been associated with malignancy. Thus, elevating cAMP through activation of adenylyl cyclase (AC) or by inhibition of phosphodiesterase (PDE) may be therapeutically beneficial. Here, we demonstrate that elevated cAMP levels suppress growth in C6

Articles

Phosphodiesterases

Cyclic nucleotide phosphodiesterases (PDEs) catalyze the hydrolysis of cAMP and/or cGMP. There are 11 different mammalian PDE families.

Discover Bioactive Molecules for Nucleotides

Cyclic nucleotides like cAMP modulate cell function via PKA activation and ion channels.

磷酸二酯酶类

环核苷酸磷酸二酯酶 (PDEs) 催化 cAMP 和/或 cGMP 的水解。存在有11种不同的哺乳动物PDE家族。

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