BAY 73-6691

BAY 73-6691
Identifiers

IUPAC name 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^Y
PubChem (CID)	16078952
ChemSpider	21171546^Y
ChEMBL	CHEMBL1513993
Chemical and physical data
Formula	C₁₅H₁₂ClF₃N₄O
Molar mass	356.730 g/mol
3D model (Jmol)	Interactive image
SMILES C[C@H](CC1=NC(=O)C2=CNN(C2=N1)C3=CC=CC=C3Cl)C(F)(F)F
InChI 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^Y Key:FFPXPXOAFQCNBS-MRVPVSSYSA-N^Y
(verify)

BAY 73-6691 is a drug developed by Bayer for the treatment of Alzheimer's disease. It was the first compound developed that acts as a phosphodiesterase inhibitor selective for the PDE9A subtype. The PDE9A enzyme is expressed primarily in the brain, with high concentrations in the cerebellum, neocortex, striatum, and hippocampus, and acts to limit the cGMP-mediated signal transduction which occurs following glutamate binding to NMDA receptors. Consequently, selective PDE9A inhibitors were predicted to prolong intracellular responses to glutamate and enhance glutamate signalling, and since this process is known to be involved in learning and memory, PDE9A inhibitors should have a nootropic effect and may be useful in the treatment of Alzheimer's.^[1]

Animal studies have confirmed these expectations, and BAY 73-6691 has been shown to improve learning and memory in rats.^[2] As the first selective PDE_9A inhibitor to be developed, it is also widely used in research into the function of this enzyme subtype. However pre-clinical research is at an early stage and it is not yet known whether BAY 73-6691 will prove suitable to progress to human trials, or if it will remain merely a laboratory research tool.

References

↑ Wunder F, Tersteegen A, Rebmann A, Erb C, Fahrig T, Hendrix M. Characterization of the first potent and selective PDE9 inhibitor using a cGMP reporter cell line. Molecular Pharmacology. 2005 Dec;68(6):1775-81. PMID 16150925
↑ 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. PMID 18674549

PDE inhibitors

PDE1	MMPX SCH-51866 Vinpocetine

PDE2	BAY 60-7550 EHNA Oxindole PDP

PDE3	Adibendan Amrinone (inamrinone) Anagrelide Bucladesine Cilostamide Cilostazol Enoximone Imazodan KMUP-1 Meribendan Milrinone Olprinone Parogrelil Pimobendan Quazinone RPL-554 Siguazodan Tetomilast Tofimilast Trequinsin Vesnarinone

PDE4	Apremilast Arofylline Atizoram Catramilast CC-1088 CDP-840 CGH-2466 Cilomilast Cipamfylline CP-80633 Crisaborole Denbutylline Drotaverine Etazolate Filaminast Glaucine HT-0712 ICI-63197 Indimilast Irsogladine Lavamilast Lirimilast Luteolin Mesembrenone Mesembrine Mesopram Oglemilast Piclamilast Revamilast Ro 20-1724 Roflumilast Rolipram Ronomilast RPL-554 RS-25344 YM-976

PDE5	Acetildenafil Aildenafil Avanafil Beminafil Benzamidenafil Dasantafil Icariin Gisadenafil Homosildenafil Lodenafil Mirodenafil MY-5445 Nitrosoprodenafil Sildenafil Sulfoaildenafil T-0156 Tadalafil Udenafil Vardenafil

PDE7	BRL-50481

PDE9	BAY 73-6691 PF-04447943

PDE10	Papaverine PF-2545920 TC-E 5005 Tofisopam

PDE11	BC11-38

Non-selective	Aminophylline Caffeine Choline theophyllinate CPX Dipyridamole Doxofylline Enprofylline Ibudilast IBMX Luteolin Paraxanthine Pentoxifylline Propentofylline SCH-51866 Theobromine Theophylline Zaprinast Zardaverine

Unsorted	Benafentrine Carbazeran Diazepam Diphylline Doxofylline DPCPX Furafylline Lisofylline MDL-12330A Moxaverine Oxagrelate Pentifylline Proxyphylline Pumafentrine Quercetin Satigrel Tolafentrine Trapidil

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