Synonym: 1-(2-Chlorophenyl)-6-[(2R)-3,3,3-trifluoro-2-methylpropyl]-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidine-4-one
CAS Number: 794568-92-6
Empirical Formula (Hill Notation): C15H12ClF3N4O
Molecular Weight: 356.73
MDL Number: MFCD08705319
Linear Formula: C15H12ClF3N4O
Product Type: Chemical
| assay |
≥98% (HPLC) |
| color |
off-white |
| form |
powder |
| 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 |
| originator |
Bayer |
| Quality Level |
100  |
| SMILES string |
C[C@H](CC1=Nc2c(cnn2-c3ccccc3Cl)C(=O)N1)C(F)(F)F |
| solubility |
DMSO: >20 mg/mL |
| storage temp. |
2-8°C |
| 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. |
| 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 . |
| Features and Benefits: |
This compound is featured on the Phosphodiesterases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here . |
| Features and Benefits: |
This compound was developed by Bayer . To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here . |
| Packaging: |
5, 25 mg in glass bottle |
| Purity |
≥98% (HPLC) |
| Storage Temp. |
2-8°C |
| UNSPSC |
41106305 |
GHS06