SML2271
ADX-47273
≥98% (HPLC)
别名:
(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
方案
≥98% (HPLC)
表单
powder
旋光性
[α]/D +90 to +110°, c = 0.1 in chloroform-d
颜色
white to beige
溶解性
DMSO: 2 mg/mL, clear
储存温度
−20°C
SMILES字符串
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
生化/生理作用
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.
储存分类代码
11 - Combustible Solids
WGK
WGK 3
闪点(°F)
Not applicable
闪点(°C)
Not applicable
法规信息
新产品
此项目有
历史批次信息供参考:
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
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
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
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