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ADX-47273

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This is an old revision of this page, as edited by The chemistds (talk | contribs) at 15:18, 26 November 2011 (added CSID, (Std)InChI & (Std)InChIKey). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Revision as of 15:18, 26 November 2011 by The chemistds (talk | contribs) (added CSID, (Std)InChI & (Std)InChIKey)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff) Pharmaceutical compound
ADX-47273
Identifiers
IUPAC name
  • (S)-(4-fluorophenyl)-(3--oxadiazol-5-yl]piperidin-1-yl)methanone
PubChem CID
IUPHAR/BPS
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H17F2N3O2
Molar mass369.364 g/mol g·mol
3D model (JSmol)
SMILES
  • Fc1ccc(cc1)C(=O)N4CCC(c2nc(no2)c3ccc(F)cc3)C4
InChI
  • InChI=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
  • Key:VXQCCZHCFBHTTD-HNNXBMFYSA-N
  (verify)

ADX-47273 is a drug used in scientific research which acts as a positive allosteric modulator selective for the metabotropic glutamate receptor subtype mGluR5. It has nootropic and antipsychotic effects in animal studies, and has been used as a lead compound to develop improved derivatives.


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References

  1. de Paulis T, Hemstapat K, Chen Y, Zhang Y, Saleh S, Alagille D, Baldwin RM, Tamagnan GD, Conn PJ (2006). "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 of Medicinal Chemistry. 49 (11): 3332–44. doi:10.1021/jm051252j. PMID 16722652. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  2. 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 (2008). "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". The Journal of Pharmacology and Experimental Therapeutics. 327 (3): 827–39. doi:10.1124/jpet.108.136580. PMID 18753411. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  3. Engers DW, Rodriguez AL, Williams R, Hammond AS, Venable D, Oluwatola O, Sulikowski GA, Conn PJ, Lindsley CW (2009). "Synthesis, SAR and unanticipated pharmacological profiles of analogues of the mGluR5 ago-potentiator ADX-47273". Chemmedchem. 4 (4): 505–11. doi:10.1002/cmdc.200800357. PMC 2865690. PMID 19197923. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
Glutamate receptor modulators
Ionotropic glutamate receptor modulators
AMPARTooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor
KARTooltip Kainate receptor
NMDARTooltip N-Methyl-D-aspartate receptor
Metabotropic glutamate receptor modulators
Group I
mGluR1Tooltip Metabotropic glutamate receptor 1
mGluR5Tooltip Metabotropic glutamate receptor 5
Group II
mGluR2Tooltip Metabotropic glutamate receptor 2
mGluR3Tooltip Metabotropic glutamate receptor 3
Group III
mGluR4Tooltip Metabotropic glutamate receptor 4
mGluR6Tooltip Metabotropic glutamate receptor 6
mGluR7Tooltip Metabotropic glutamate receptor 7
mGluR8Tooltip Metabotropic glutamate receptor 8
See also: Receptor/signaling modulators • Ionotropic glutamate receptor modulators • Glutamate metabolism/transport modulators
Categories: