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
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关于此项目
经验公式（希尔记法）:
C20H17F2N3O2
化学文摘社编号:
分子量:
369.36
UNSPSC Code:
12352200
MDL number:
NACRES:
NA.21
Assay:
≥98% (HPLC)
Form:
powder
产品名称
ADX-47273, ≥98% (HPLC)
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
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.
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
法规信息
新产品
此项目有
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
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
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
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
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
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