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Merck

SML2271

ADX-47273

≥98% (HPLC)

Synonim(y):

(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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Informacje o tej pozycji

Wzór empiryczny (zapis Hilla):
C20H17F2N3O2
Numer CAS:
851881-60-2
Masa cząsteczkowa:
369.36
UNSPSC Code:
12352200
MDL number:
MFCD17167026
NACRES:
NA.21
Assay:
≥98% (HPLC)
Form:
powder

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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

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Ta pozycja
SML2212SML0912SML1883
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.
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Klasa składowania

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Wybierz jedną z najnowszych wersji:

Certyfikaty analizy (CoA)

Lot/Batch Number
0000051071
0000051072
0000043177

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Dokumenty związane z niedawno zakupionymi produktami zostały zamieszczone w Bibliotece dokumentów.

Odwiedź Bibliotekę dokumentów

Sarah N Isherwood et al.
Journal of neurochemistry, 145(2), 111-124 (2018-01-10)
Dysregulation of prefrontal cortical glutamatergic signalling via NMDA receptor hypofunction has been implicated in cognitive dysfunction and impaired inhibitory control in such neuropsychiatric disorders as schizophrenia, attention-deficit hyperactivity disorder and drug addiction. Although NMDA receptors functionally interact with metabotropic glutamate
Arthur Bikbaev et al.
Neuropharmacology, 115, 20-29 (2016-07-11)
Hippocampal synaptic plasticity and learning are regulated by metabotropic glutamate receptors (mGlu) and particularly by mGlu5. In the hippocampus, synaptic plasticity is tightly linked to neuronal network oscillations in theta (5-10 Hz) and gamma (∼30-100 Hz) frequency ranges, and specific changes in
Tomas de Paulis et al.
Journal of medicinal chemistry, 49(11), 3332-3344 (2006-05-26)
CDPPB [3-cyano-N-(1,3-diphenyl-1H-pyrazol-5-yl)benzamide] was recently described as the first centrally active, positive allosteric modulator of rat and human metabotropic glutamate receptor (mGluR) mGluR5 subtype. We explored the structural requirements for potentiation of glutamate-induced calcium release in naturally expressed mGluR5 in cultured
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
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
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Numer pozycji handlu globalnego

SKUNUMER GTIN
SML2271-5MG04061835255146
SML2271-25MG04061835255139

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