ADX-47273
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MedKoo CAT#: 522386

CAS#: 851881-60-2

Description: ADX-47273 is a potent and selective mGluR5 receptor PAM (positive allosteric modulator), EC50 = 0.17 μm, with no effect on other mGluR subtypes. In vivo, ADX47273 increased extracellular signal-regulated kinase and cAMP-responsive element-binding protein phosphorylation in hippocampus and prefrontal cortex, both of which are critical for glutamate-mediated signal transduction mechanisms. The mGluR (metabotropic glutamate receptor) is a group of G-protein coupled receptors and is active through an indirect metabotropic process. It plays a critical role in regulating synaptic plasticity and neural network activity.


Chemical Structure

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ADX-47273
CAS# 851881-60-2

Theoretical Analysis

MedKoo Cat#: 522386
Name: ADX-47273
CAS#: 851881-60-2
Chemical Formula: C20H17F2N3O2
Exact Mass: 369.12888
Molecular Weight: 369.37
Elemental Analysis: C, 65.03; H, 4.64; F, 10.29; N, 11.38; O, 8.66

Price and Availability

Size Price Availability Quantity
10.0mg USD 150.0 2 Weeks
25.0mg USD 250.0 2 Weeks
50.0mg USD 450.0 2 Weeks
100.0mg USD 650.0 2 Weeks
200.0mg USD 950.0 2 Weeks
500.0mg USD 1750.0 2 Weeks
1.0g USD 2950.0 2 Weeks
2.0g USD 3950.0 2 Weeks
5.0g USD 6750.0 2 Weeks
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Synonym: ADX-47273; ADX 47273; ADX47273.

IUPAC/Chemical Name: (S)-(4-fluorophenyl)(3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)piperidin-1-yl)methanone

InChi Key: VXQCCZHCFBHTTD-HNNXBMFYSA-N

InChi Code: 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

SMILES Code: O=C(C1=CC=C(F)C=C1)N2C[C@@H](C3=NC(C4=CC=C(F)C=C4)=NO3)CCC2

Appearance: Solid powder

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

Preparing Stock Solutions

The following data is based on the product molecular weight 369.37 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.

Recalculate based on batch purity %
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

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1: Xu J, Zhu Y, Kraniotis S, He Q, Marshall JJ, Nomura T, Stauffer SR, Lindsley CW, Conn PJ, Contractor A. Potentiating mGluR5 function with a positive allosteric modulator enhances adaptive learning. Learn Mem. 2013 Jul 18;20(8):438-45. doi: 10.1101/lm.031666.113. PubMed PMID: 23869026; PubMed Central PMCID: PMC3718201.

2: Kjaerby C, Bundgaard C, Fejgin K, Kristiansen U, Dalby NO. Repeated potentiation of the metabotropic glutamate receptor 5 and the alpha 7 nicotinic acetylcholine receptor modulates behavioural and GABAergic deficits induced by early postnatal phencyclidine (PCP) treatment. Neuropharmacology. 2013 Sep;72:157-68. doi: 10.1016/j.neuropharm.2013.04.041. Epub 2013 May 2. PubMed PMID: 23643744.

3: Clifton NE, Morisot N, Girardon S, Millan MJ, Loiseau F. Enhancement of social novelty discrimination by positive allosteric modulators at metabotropic glutamate 5 receptors: adolescent administration prevents adult-onset deficits induced by neonatal treatment with phencyclidine. Psychopharmacology (Berl). 2013 Feb;225(3):579-94. doi: 10.1007/s00213-012-2845-3. Epub 2012 Sep 16. PubMed PMID: 22983144.

4: Stauffer SR. Progress toward positive allosteric modulators of the metabotropic glutamate receptor subtype 5 (mGluR5). ACS Chem Neurosci. 2011 Aug 17;2(8):450-70. doi: 10.1021/cn2000519. Epub 2011 Jun 27. Review. PubMed PMID: 22860171; PubMed Central PMCID: PMC3369763.

5: Kroker KS, Rast G, Rosenbrock H. Differential effect of the mGlu5 receptor positive allosteric modulator ADX-47273 on early and late hippocampal LTP. Neuropharmacology. 2011 Sep;61(4):707-14. doi: 10.1016/j.neuropharm.2011.05.014. Epub 2011 May 27. PubMed PMID: 21640734.

6: Lamb JP, Engers DW, Niswender CM, Rodriguez AL, Venable DF, Conn PJ, Lindsley CW. Discovery of molecular switches within the ADX-47273 mGlu5 PAM scaffold that modulate modes of pharmacology to afford potent mGlu5 NAMs, PAMs and partial antagonists. Bioorg Med Chem Lett. 2011 May 1;21(9):2711-4. doi: 10.1016/j.bmcl.2010.11.119. Epub 2010 Dec 3. PubMed PMID: 21183344; PubMed Central PMCID: PMC3179182.

7: Rosenbrock H, Kramer G, Hobson S, Koros E, Grundl M, Grauert M, Reymann KG, Schröder UH. Functional interaction of metabotropic glutamate receptor 5 and NMDA-receptor by a metabotropic glutamate receptor 5 positive allosteric modulator. Eur J Pharmacol. 2010 Aug 10;639(1-3):40-6. doi: 10.1016/j.ejphar.2010.02.057. Epub 2010 Apr 2. PubMed PMID: 20371241.

8: Schlumberger C, Pietraszek M, Gravius A, Danysz W. Effects of a positive allosteric modulator of mGluR5 ADX47273 on conditioned avoidance response and PCP-induced hyperlocomotion in the rat as models for schizophrenia. Pharmacol Biochem Behav. 2010 Mar;95(1):23-30. doi: 10.1016/j.pbb.2009.12.002. Epub 2009 Dec 5. PubMed PMID: 19995568.

9: Schlumberger C, Pietraszek M, Gravius A, Klein KU, Greco S, Morè L, Danysz W. Comparison of the mGlu(5) receptor positive allosteric modulator ADX47273 and the mGlu(2/3) receptor agonist LY354740 in tests for antipsychotic-like activity. Eur J Pharmacol. 2009 Nov 25;623(1-3):73-83. doi: 10.1016/j.ejphar.2009.09.006. Epub 2009 Sep 16. PubMed PMID: 19765575.

10: Bradley SJ, Watson JM, Challiss RA. Effects of positive allosteric modulators on single-cell oscillatory Ca2+ signaling initiated by the type 5 metabotropic glutamate receptor. Mol Pharmacol. 2009 Dec;76(6):1302-13. doi: 10.1124/mol.109.059170. Epub 2009 Sep 8. PubMed PMID: 19737913; PubMed Central PMCID: PMC2784724.

11: Engers DW, Rodriguez AL, Williams R, Hammond AS, Venable D, Oluwatola O, Sulikowski GA, Conn PJ, Lindsley CW. Synthesis, SAR and unanticipated pharmacological profiles of analogues of the mGluR5 ago-potentiator ADX-47273. ChemMedChem. 2009 Apr;4(4):505-11. doi: 10.1002/cmdc.200800357. PubMed PMID: 19197923; PubMed Central PMCID: PMC2865690.

12: 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. ADX47273 [S-(4-fluoro-phenyl)-{3-[3-(4-fluoro-phenyl)-[1,2,4]-oxadiazol-5-yl]-piperidin-1- yl}-methanone]: a novel metabotropic glutamate receptor 5-selective positive allosteric modulator with preclinical antipsychotic-like and procognitive activities. J Pharmacol Exp Ther. 2008 Dec;327(3):827-39. doi: 10.1124/jpet.108.136580. Epub 2008 Aug 27. PubMed PMID: 18753411.

13: de Paulis T, Hemstapat K, Chen Y, Zhang Y, Saleh S, Alagille D, Baldwin RM, Tamagnan GD, Conn PJ. 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. J Med Chem. 2006 Jun 1;49(11):3332-44. PubMed PMID: 16722652.