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B3561

Sigma-Aldrich

BAY 73-6691

≥98% (HPLC), powder

Sinónimos:

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

Fórmula empírica (notación de Hill):
C15H12ClF3N4O
Número de CAS:
794568-92-6
Peso molecular:
356.73
Número MDL:
MFCD08705319
Código UNSPSC:
41106305
ID de la sustancia en PubChem:
24724419
NACRES:
NA.77

Nivel de calidad

100

Análisis

≥98% (HPLC)

formulario

powder

color

off-white

solubilidad

DMSO: >20 mg/mL

emisor

Bayer

temp. de almacenamiento

2-8°C

cadena SMILES

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

Clave InChI

FFPXPXOAFQCNBS-MRVPVSSYSA-N

Aplicación

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.

Acciones bioquímicas o fisiológicas

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.†

Características y beneficios

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.

Pictogramas

Skull and crossbones
GHS06

Palabra de señalización

Danger

Frases de peligro

H300,H315,H319,H335,H413

Clasificaciones de peligro

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

Órganos de actuación

Respiratory system

Código de clase de almacenamiento

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

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

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

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Visite la Librería de documentos

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)
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)
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
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

Artículos

Phosphodiesterases

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

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