| Revision as of 10:44, 17 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 462577638 of page ADX-47273 for the Chem/Drugbox validation project (updated: 'ChEMBL'). |
Latest revision as of 09:49, 10 January 2024 edit Maxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers31,042 edits Added s2cid. Added the cs1 style template to denote Vancouver ("vanc") citation style, because references contain "vauthors" attribute to specify the list of authors. |
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{{Short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{cs1 config|name-list-style=vanc}} |
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{{Drugbox |
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{{Drugbox |
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| Watchedfields = changed |
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| verifiedrevid = 375211715 |
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| verifiedrevid = 477346495 |
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| IUPAC_name = (S)-(4-fluorophenyl)-(3--oxadiazol-5-yl]piperidin-1-yl)methanone |
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| IUPAC_name = (S)-(4-fluorophenyl)-(3--oxadiazol-5-yl]piperidin-1-yl)methanone |
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| image = ADX-47273_structure.png |
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| image = ADX-47273.svg |
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| width = 200 |
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| width = 200 |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
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| legal_status = |
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| routes_of_administration = |
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| routes_of_administration = |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| metabolism = |
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| metabolism = |
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| elimination_half-life = |
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| elimination_half-life = |
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| excretion = |
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| excretion = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = |
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| CAS_number = 851881-60-2 |
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| CAS_supplemental = <BR>851881-59-9 (''R'' isomer),<BR>837413-22-6 (racemate) |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 4C4P7L0W63 |
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| ATC_prefix = |
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| ATC_prefix = |
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| ATC_suffix = |
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| ATC_suffix = |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 381055 |
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| ChEMBL = 381055 |
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| PubChem = 11383075 |
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| PubChem = 11383075 |
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| IUPHAR_ligand = 1420 |
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| IUPHAR_ligand = 1420 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| DrugBank = |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 9557988 |
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| ChemSpiderID = 9557988 |
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| SMILES = Fc1ccc(cc1)C(=O)N4CCC(c2nc(no2)c3ccc(F)cc3)C4 |
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| InChI = 1/C20H17F2N3O2/c21-16-7-3-13(4-8-16)18-23-19(27-24-18)15-2-1-11-25(12-15)20(26)14-5-9-17(22)10-6-14/h3-10,15H,1-2,11-12H2/t15-/m0/s1 |
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| InChIKey = VXQCCZHCFBHTTD-HNNXBMFYBQ |
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| StdInChI = 1S/C20H17F2N3O2/c21-16-7-3-13(4-8-16)18-23-19(27-24-18)15-2-1-11-25(12-15)20(26)14-5-9-17(22)10-6-14/h3-10,15H,1-2,11-12H2/t15-/m0/s1 |
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| StdInChIKey = VXQCCZHCFBHTTD-HNNXBMFYSA-N |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=20 | H=17 | F=2 | N=3 | O=2 |
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| C=20 | H=17 | F=2 | N=3 | O=2 |
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| smiles = FC1=CC=C(C(N2CCC(C2)C3=NC(C4=CC=C(F)C=C4)=NO3)=O)C=C1 |
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| molecular_weight = 369.364 g/mol |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| smiles = c4cc(F)ccc4-c3nc(on3)C(C2)CCCN2C(=O)c1ccc(F)cc1 |
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| StdInChI = 1S/C20H17F2N3O2/c21-16-7-3-13(4-8-16)18-23-19(27-24-18)15-2-1-11-25(12-15)20(26)14-5-9-17(22)10-6-14/h3-10,15H,1-2,11-12H2/t15-/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = VXQCCZHCFBHTTD-HNNXBMFYSA-N |
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}} |
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}} |
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'''ADX-47273''' is a research pharmaceutical developed by ] which acts as a ] (PAM) selective for the ] subtype ].<ref name="pmid16722652">{{cite journal |vauthors =de Paulis T, Hemstapat K, Chen Y, Zhang Y, Saleh S, Alagille D, Baldwin RM, Tamagnan GD, Conn PJ |title=Substituent effects of N-(1,3-diphenyl-1H-pyrazol-5-yl)benzamides on positive allosteric modulation of the metabotropic glutamate-5 receptor in rat cortical astrocytes |journal=Journal of Medicinal Chemistry |volume=49 |issue=11 |pages=3332–44 |date=June 2006 |pmid=16722652 |doi=10.1021/jm051252j }}</ref><ref>{{cite journal|last1=Stauffer|first1=Shaun R.|title=Progress toward Positive Allosteric Modulators of the Metabotropic Glutamate Receptor Subtype 5 (mGlu5)|journal=ACS Chemical Neuroscience|date=17 August 2011|volume=2|issue=8|pages=450–470|doi=10.1021/cn2000519|pmc=3369763|pmid=22860171}}</ref> It has ] and ] effects in animal studies,<ref name="pmid18753411">{{cite journal |vauthors =Liu F, Grauer S, Kelley C, Navarra R, Graf R, Zhang G, Atkinson PJ, Popiolek M, Wantuch C, Khawaja X, Smith D, Olsen M, Kouranova E, Lai M, Pruthi F, Pulicicchio C, Day M, Gilbert A, Pausch MH, Brandon NJ, Beyer CE, Comery TA, Logue S, Rosenzweig-Lipson S, Marquis KL |title=ADX47273 -oxadiazol-5-yl]-piperidin-1-yl}-methanone]: a novel metabotropic glutamate receptor 5-selective positive allosteric modulator with preclinical antipsychotic-like and procognitive activities |journal=The Journal of Pharmacology and Experimental Therapeutics |volume=327 |issue=3 |pages=827–39 |date=December 2008|pmid=18753411 |doi=10.1124/jpet.108.136580 |s2cid=19362501 }}</ref> and has been used as a ] to develop improved derivatives.<ref name="pmid19197923">{{cite journal |vauthors =Engers DW, Rodriguez AL, Williams R, Hammond AS, Venable D, Oluwatola O, Sulikowski GA, Conn PJ, Lindsley CW |title=Synthesis, SAR and unanticipated pharmacological profiles of analogues of the mGluR5 ago-potentiator ADX-47273 |journal=ChemMedChem |volume=4 |issue=4 |pages=505–11 |date=April 2009 |pmid=19197923 |doi=10.1002/cmdc.200800357 |pmc=2865690}}</ref> |
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==See also== |
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* ] |
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* ] |
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==References== |
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{{Reflist|2}} |
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{{Metabotropic glutamate receptor modulators}} |
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] |
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] |
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{{nervous-system-drug-stub}} |