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Merck

SML2271

ADX-47273

≥98% (HPLC)

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

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About This Item

Empirical Formula (Hill Notation):
C20H17F2N3O2
CAS Number:
851881-60-2
Molecular Weight:
369.36
UNSPSC Code:
12352200
MDL number:
MFCD17167026
NACRES:
NA.21
Assay:
≥98% (HPLC)
Form:
powder

Key Documents

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InChI key

VXQCCZHCFBHTTD-HNNXBMFYSA-N

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 string

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

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

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ADX-47273 ≥98% (HPLC)

Sigma-Aldrich

SML2271

ADX-47273

RWJ 67657 ≥98% (HPLC)

Sigma-Aldrich

SML2212

RWJ 67657

SB 674042 ≥98% (HPLC)

Sigma-Aldrich

SML0912

SB 674042

AR231453 ≥98% (HPLC)

Sigma-Aldrich

SML1883

AR231453

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

form

powder

form

powder

form

powder

form

powder

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

solubility

DMSO: 2 mg/mL, clear

solubility

DMSO: 2 mg/mL, clear

solubility

DMSO: 10 mg/mL, clear

solubility

DMSO: 20 mg/mL, clear

color

white to beige

color

white to beige

color

white to beige

color

white to beige

optical activity

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

optical activity

-

optical activity

-

optical activity

-

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).
Brain-penetrant, potent and selective mGlu5 (mGluR5) positive allosteric modulator (PAM) with antipsychotic and procognitive efficacy in mice and rats in vivo.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000051071
0000051072
0000043177

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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
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
A Ahnaou et al.
Psychopharmacology, 232(6), 1107-1122 (2014-10-18)
Evidence is emerging that positive and negative modulation of the metabotropic glutamate (mGluR5) receptors has the potential for treating cognitive deficits and neuroprotection associated with psychiatric and neurodegenerative diseases, respectively. Sleep and synchronisation of disparate neuronal networks are critically involved
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
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
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