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B3561 Sigma-Aldrich

BAY 73-6691

≥98% (HPLC), powder

Synonym: 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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Properties

Related Categories Approved Therapeutics/Drug Candidates, B, Bayer, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules,
Quality Level   100
assay   ≥98% (HPLC)
form   powder
color   off-white
solubility   DMSO: >20 mg/mL
originator   Bayer
storage temp.   2-8°C
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
InChI key   FFPXPXOAFQCNBS-MRVPVSSYSA-N

Description

Packaging

5, 25 mg in glass bottle

Biochem/physiol Actions

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.

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
3

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Discover Bioactive Small Molecules for Cyclic Nucleotides

Transmission of an extracellular signal across the cell membrane is initiated by activation of many types of hormone and neurotransmitter receptors, such as G-protein coupled receptors (GPCRs), and c...
Keywords: Antivirals, Cancer, Cardiovascular, Cellular processes, Diabetes, Diseases, Hormones, Neurotransmitters

Phosphodiesterases

Cyclic nucleotide phosphodiesterases (PDEs) catalyze the hydrolysis of cAMP and/or cGMP. They function with adenylyl and guanylyl cyclases to regulate the amplitude and duration of responses triggere...
Keywords: Amplification, Atomic absorption spectroscopy, Catalysis, Diabetes, Gene expression, Genetic, Hormones, Inflammation, Neurotransmitters, Obesity, Parkinson Disease, Phosphorylations, Physiological Processes, Schizophrenia, Transduction

Peer-Reviewed Papers
15

References

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