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Revision as of 23:02, 18 November 2011 editThe chemistds (talk | contribs)Extended confirmed users5,761 edits added CSID, (Std)InChI & (Std)InChIKey← Previous edit Latest revision as of 19:55, 7 September 2024 edit undoJWBE (talk | contribs)Extended confirmed users10,111 edits removed Category:Chloroarenes; added Category:2-Chlorophenyl compounds using HotCat 
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{{Short description|Chemical compound}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 422023782 | verifiedrevid = 461349234
| IUPAC_name = 1-(2-chlorophenyl)-6--1,5-dihydro-4H-pyrazolopyrimidine-4-one | IUPAC_name = 1-(2-Chlorophenyl)-6--1,5-dihydro-4''H''-pyrazolopyrimidine-4-one
| image = BAY73-6691_structure.png | image = BAY 73-6691.svg


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category = | pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> | legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status = | legal_status =
| routes_of_administration = | routes_of_administration =


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = | bioavailability =
| protein_bound = | protein_bound =
| metabolism = | metabolism =
| elimination_half-life = | elimination_half-life =
| excretion = | excretion =


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 794568-92-6 | CAS_number = 794568-92-6
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | ATC_prefix =
| UNII = 80ZTV3INTW
⚫ | ATC_suffix =
⚫ | ATC_prefix = None
⚫ | ATC_suffix =
| PubChem = 16078952 | PubChem = 16078952
| ChEBI = 231440
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = | DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 21171546 | ChemSpiderID = 21171546
⚫ | InChI = 1/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
| ChEMBL_Ref = {{ebicite|changed|EBI}}
⚫ | InChIKey = FFPXPXOAFQCNBS-MRVPVSSYBD
| ChEMBL = 1513993
| StdInChI = 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
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = FFPXPXOAFQCNBS-MRVPVSSYSA-N
⚫ | StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫ | StdInChIKey = FFPXPXOAFQCNBS-MRVPVSSYSA-N


<!--Chemical data--> <!--Chemical data-->
| C=15 | H=12 | Cl=1 | F=3 | N=4 | O=1 | C=15 | H=12 | Cl=1 | F=3 | N=4 | O=1
| molecular_weight = 356.730 g/mol
| smiles = C(CC1=NC(=O)C2=CNN(C2=N1)C3=CC=CC=C3Cl)C(F)(F)F | smiles = C(CC1=NC(=O)C2=CNN(C2=N1)C3=CC=CC=C3Cl)C(F)(F)F
}} }}


'''BAY 73-6691''' is a drug developed by ] for the treatment of ]. It was the first compound developed that acts as a ] selective for the PDE<sub>9A</sub> subtype. The PDE<sub>9A</sub> enzyme is expressed primarily in the brain, with high concentrations in the ], ], ], and ], and acts to limit the ]-mediated ] which occurs following ] binding to ]s. Consequently selective PDE<sub>9A</sub> 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, PDE<sub>9A</sub> inhibitors should have a ] effect and may be useful in the treatment of Alzheimer's.<ref>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</ref> '''BAY 73-6691''' is a drug developed by ] for the treatment of ]. It was the first compound developed that acts as a ] selective for the ] subtype. The PDE9A enzyme is expressed primarily in the brain, with high concentrations in the ], ], ], and ], and acts to limit the ]-mediated ] which occurs following ] binding to ]s. 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 ] effect and may be useful in the treatment of Alzheimer's.<ref>{{cite journal | vauthors = Wunder F, Tersteegen A, Rebmann A, Erb C, Fahrig T, Hendrix M | title = Characterization of the first potent and selective PDE9 inhibitor using a cGMP reporter cell line | journal = Molecular Pharmacology | volume = 68 | issue = 6 | pages = 1775–81 | date = December 2005 | pmid = 16150925 | doi = 10.1124/mol.105.017608 | s2cid = 2054966 }}</ref>


Animal studies have confirmed these expectations, and BAY 73-6691 has been shown to improve learning and memory in rats.<ref>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</ref> As the first selective PDE<sub>9A</sub> 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. Animal studies have confirmed these expectations, and BAY 73-6691 has been shown to improve learning and memory in rats.<ref>{{cite journal | vauthors = 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 | display-authors = 6 | title = The novel selective PDE9 inhibitor BAY 73-6691 improves learning and memory in rodents | journal = Neuropharmacology | volume = 55 | issue = 5 | pages = 908–18 | date = October 2008 | pmid = 18674549 | doi = 10.1016/j.neuropharm.2008.07.005 | hdl = 1874/32084 | s2cid = 24171186 | hdl-access = free }}</ref> As the first selective PDE<sub>9A</sub> 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 ==

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⚫ ==References==
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{{Phosphodiesterase inhibitors}} {{Phosphodiesterase inhibitors}}


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