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B3561

Sigma-Aldrich

BAY 73-6691

≥98% (HPLC), powder

Synonyme(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

Formule empirique (notation de Hill):
C15H12ClF3N4O
Numéro CAS:
794568-92-6
Poids moléculaire :
356.73
Numéro MDL:
MFCD08705319
Code UNSPSC :
41106305
ID de substance PubChem :
24724419
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Couleur

off-white

Solubilité

DMSO: >20 mg/mL

Auteur

Bayer

Température de stockage

2-8°C

Chaîne 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

Clé InChI

FFPXPXOAFQCNBS-MRVPVSSYSA-N

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.

Actions biochimiques/physiologiques

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.†

Caractéristiques et avantages

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.

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H300,H315,H319,H335,H413

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

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)
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)
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.

Phosphodiesterases

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

Phosphodiesterases

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

Phosphodiesterases

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

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