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

Properties

• 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

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.

Safety Information

• pictograms: GHS06
• signalword: Danger
• hcodes: H300,H315,H319,H335,H413
• pcodes: P273 - P301 + P310 + P330 - P302 + P352 - P305 + P351 + P338
• 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_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges