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SML2271

Sigma-Aldrich

ADX-47273

≥98% (HPLC)

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Synonym(s):
(4-Fluorophenyl)[(3S)-3-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]-1-piperidinyl]methanone, (S)-(4-Fluorophenyl)-{3-[3-(4-fluorophenyl)-[1,2,4]oxadiazol-5-yl]-piperidin-1-yl}-methanone, ADX 47273, ADX47273
Empirical Formula (Hill Notation):
C20H17F2N3O2
CAS Number:
851881-60-2
Molecular Weight:
369.36
MDL number:
MFCD17167026

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D +90 to +110°, c = 0.1 in chloroform-d

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

FC1=CC=C(C=C1)C2=NOC([C@@H]3CN(CCC3)C(C4=CC=C(C=C4)F)=O)=N2

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

InChI key

VXQCCZHCFBHTTD-HNNXBMFYSA-N

Biochem/physiol Actions

ADX-47273 is a brain-penetrating, potent and selective metabotropic glutamate receptor 5 (mGlu5; mGluR5) positive allosteric modulator (PAM) that enhances glutamate-stimulated Ca2+ response in rat cortical astrocytes (EC50 = 170 nM, Emax = 380%; [glutamate] = EC20 = 200 nM) via direct mGlu5 binding in a MPEP-, but not Quisqualate-, competitive manner (Ki = 4.3 μM against 2 nM MPEP; rat mGlu5 HEK293) with little mGlu5 agonist activity, no potency toward other rat/human family III GPCRs (mGlu1–8 and GABA-B), nor affinity to 56 GPCRs/transporters/enzymes/ion channels. ADX-47273 shows in vivo antipsychotic-like and procognitive efficacy in mice and rats in vivo (1-300 mg/kg i.p.) with good pharmacokinetic properties (B/P ratio >2, bioavailability ∼40%, T1/2 ∼2 hrs in rats).

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Sarah N Isherwood et al.
Psychopharmacology, 232(18), 3327-3344 (2015-06-13)
Impaired N-methyl-D-aspartate (NMDA) receptor signalling underlies several psychiatric disorders that express high levels of impulsivity. Although synergistic interactions exist between NMDA receptors and metabotropic glutamate receptor 5 (mGluR5), the significance of this interaction for impulsivity is unknown. This study aims
Feng Liu et al.
The Journal of pharmacology and experimental therapeutics, 327(3), 827-839 (2008-08-30)
Positive allosteric modulators (PAMs) of metabotropic glutamate receptor subtype 5 (mGlu5) enhance N-methyl-d-aspartate receptor function and may represent a novel approach for the treatment of schizophrenia. ADX47273 [S-(4-fluoro-phenyl)-{3-[3-(4-fluoro-phenyl)-[1,2,4]oxadiazol-5-yl]-piperidin-1-yl}-methanone], a recently identified potent and selective mGlu5 PAM, increased (9-fold) the response
Kazuto Yamazaki et al.
Journal of biomolecular screening, 21(10), 1054-1064 (2017-02-01)
Because neurons are difficult to obtain from humans, generating functional neurons from human induced pluripotent stem cells (hiPSCs) is important for establishing physiological or disease-relevant screening systems for drug discovery. To examine the culture conditions leading to efficient differentiation of
Jian Xu et al.
Learning & memory (Cold Spring Harbor, N.Y.), 20(8), 438-445 (2013-07-23)
Metabotropic glutamate receptor 5 (mGluR5) plays important roles in modulating neural activity and plasticity and has been associated with several neuropathological disorders. Previous work has shown that genetic ablation or pharmacological inhibition of mGluR5 disrupts fear extinction and spatial reversal
Marta Marszalek-Grabska et al.
Behavioural brain research, 338, 9-16 (2017-10-17)
Repeated exposure to and withdrawal from ethanol induces deficits in spatial reversal learning. Data indicate that metabotropic glutamate 5 (mGlu5) receptors are implicated in synaptic plasticity and learning and memory. These receptors functionally interact with N-methyl-d-aspartate (NMDA) receptors, and activation
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