Synonym
BAY-73-6691; BAY736691; BAY73-6691; UNII-80ZTV3INTW; (R)-Bay-73-6691;
IUPAC/Chemical Name
4H-Pyrazolo(3,4-d)pyrimidin-4-one, 1-(2-chlorophenyl)-1,5-dihydro-6-((2R)-3,3,3-trifluoro-2-methylpropyl)-
InChi Key
FFPXPXOAFQCNBS-MRVPVSSYSA-N
InChi Code
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
SMILES Code
O=C1C2=C(N(C3=CC=CC=C3Cl)N=C2)N=C(C[C@@H](C)C(F)(F)F)N1
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
BAY 73-6691 is a PDE9A inhibitor.
In vitro activity:
Whether BAY 73-6691 could attenuate the oxidative stress during the development of Alzheimer’s disease was evaluated in vitro. Primary cultures of SH-SY5Y cells were incubated with 20μM beta-amyloid25-35 (Aβ25-35), followed by exposure to different concentrations (50, 100, 150 and 200μg/ml) of BAY 73-6691. Treatment with BAY 73-6691 attenuated the Aβ25-35-induced cytotoxicity and oxidative stress in SH-SY5Y cells.
Reference: Brain Res. 2016 Jul 1;1642:327-335. https://www.sciencedirect.com/science/article/abs/pii/S0006899316302049?via%3Dihub
In vivo activity:
The antioxidant effect of BAY 73-6691 was evaluated in mice subjected to intracerebroventricular injection of Aβ25-35 (day 0) and treatment with BAY 73-6691 by intraperitoneal injection once daily (days 1-10). BAY 73-6691 protected Aβ25-35-induced oxidative damage in hippocampus, associated with the attenuation of impairments in hippocampal neurons. Administration of BAY 73-6691 improved learning and memory in the Morris water maze test, and restored several hippocampal memory-associated proteins.
Reference: Brain Res. 2016 Jul 1;1642:327-335. https://www.sciencedirect.com/science/article/abs/pii/S0006899316302049?via%3Dihub
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
160.0 |
448.52 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
356.73
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Li J, Liu CN, Wei N, Li XD, Liu YY, Yang R, Jia YJ. Protective effects of BAY 73-6691, a selective inhibitor of phosphodiesterase 9, on amyloid-β peptides-induced oxidative stress in in-vivo and in-vitro models of Alzheimer's disease. Brain Res. 2016 Jul 1;1642:327-335. doi: 10.1016/j.brainres.2016.04.011. Epub 2016 Apr 9. PMID: 27071547.
2. Saravani R, Karami-Tehrani F, Hashemi M, Aghaei M, Edalat R. Inhibition of phosphodiestrase 9 induces cGMP accumulation and apoptosis in human breast cancer cell lines, MCF-7 and MDA-MB-468. Cell Prolif. 2012 Jun;45(3):199-206. doi: 10.1111/j.1365-2184.2012.00819.x. Epub 2012 Apr 2. PMID: 22469131; PMCID: PMC6496613.
3. da Silva FH, Pereira MN, Franco-Penteado CF, De Nucci G, Antunes E, Claudino MA. Phosphodiesterase-9 (PDE9) inhibition with BAY 73-6691 increases corpus cavernosum relaxations mediated by nitric oxide-cyclic GMP pathway in mice. Int J Impot Res. 2013 Mar-Apr;25(2):69-73. doi: 10.1038/ijir.2012.35. Epub 2012 Oct 4. PMID: 23034509.
In vitro protocol:
1. Li J, Liu CN, Wei N, Li XD, Liu YY, Yang R, Jia YJ. Protective effects of BAY 73-6691, a selective inhibitor of phosphodiesterase 9, on amyloid-β peptides-induced oxidative stress in in-vivo and in-vitro models of Alzheimer's disease. Brain Res. 2016 Jul 1;1642:327-335. doi: 10.1016/j.brainres.2016.04.011. Epub 2016 Apr 9. PMID: 27071547.
2. Saravani R, Karami-Tehrani F, Hashemi M, Aghaei M, Edalat R. Inhibition of phosphodiestrase 9 induces cGMP accumulation and apoptosis in human breast cancer cell lines, MCF-7 and MDA-MB-468. Cell Prolif. 2012 Jun;45(3):199-206. doi: 10.1111/j.1365-2184.2012.00819.x. Epub 2012 Apr 2. PMID: 22469131; PMCID: PMC6496613.
In vivo protocol:
1. Li J, Liu CN, Wei N, Li XD, Liu YY, Yang R, Jia YJ. Protective effects of BAY 73-6691, a selective inhibitor of phosphodiesterase 9, on amyloid-β peptides-induced oxidative stress in in-vivo and in-vitro models of Alzheimer's disease. Brain Res. 2016 Jul 1;1642:327-335. doi: 10.1016/j.brainres.2016.04.011. Epub 2016 Apr 9. PMID: 27071547.
2. da Silva FH, Pereira MN, Franco-Penteado CF, De Nucci G, Antunes E, Claudino MA. Phosphodiesterase-9 (PDE9) inhibition with BAY 73-6691 increases corpus cavernosum relaxations mediated by nitric oxide-cyclic GMP pathway in mice. Int J Impot Res. 2013 Mar-Apr;25(2):69-73. doi: 10.1038/ijir.2012.35. Epub 2012 Oct 4. PMID: 23034509.
1: Li J, Liu CN, Wei N, Li XD, Liu YY, Yang R, Jia YJ. Protective effects of BAY 73-6691, a selective inhibitor of phosphodiesterase 9, on amyloid-β peptides-induced oxidative stress in in-vivo and in-vitro models of Alzheimer's disease. Brain Res. 2016 Apr 9. pii: S0006-8993(16)30204-9. doi: 10.1016/j.brainres.2016.04.011. [Epub ahead of print] PubMed PMID: 27071547.
2: da Silva FH, Pereira MN, Franco-Penteado CF, De Nucci G, Antunes E, Claudino MA. Phosphodiesterase-9 (PDE9) inhibition with BAY 73-6691 increases corpus cavernosum relaxations mediated by nitric oxide-cyclic GMP pathway in mice. Int J Impot Res. 2013 Mar-Apr;25(2):69-73. doi: 10.1038/ijir.2012.35. Epub 2012 Oct 4. PubMed PMID: 23034509.
3: van der Staay FJ, Rutten K, Bärfacker L, Devry J, Erb C, Heckroth H, Karthaus D, Tersteegen A, van Kampen M, Blokland A, Prickaerts J, Reymann KG, Schröder UH, Hendrix M. The novel selective PDE9 inhibitor BAY 73-6691 improves learning and memory in rodents. Neuropharmacology. 2008 Oct;55(5):908-18. doi: 10.1016/j.neuropharm.2008.07.005. Epub 2008 Jul 12. PubMed PMID: 18674549.
