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Merck
CN

A3230

AR-A014418

≥98% (HPLC), solid

Synonym(s):

N-(4-Methoxybenzyl)-N′-(5-nitro-1,3-thiazol-2-yl)urea

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About This Item

Empirical Formula (Hill Notation):
C12H12N4O4S
CAS Number:
487021-52-3
Molecular Weight:
308.31
NACRES:
NA.77
PubChem Substance ID:
329770820
UNSPSC Code:
12352200
MDL number:
MFCD08277040
Assay:
≥98% (HPLC)
Form:
solid
Quality level:
100

Key Documents

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InChI

1S/C12H12N4O4S/c1-20-9-4-2-8(3-5-9)6-13-11(17)15-12-14-7-10(21-12)16(18)19/h2-5,7H,6H2,1H3,(H2,13,14,15,17)

SMILES string

COc1ccc(CNC(=O)Nc2ncc(s2)[N+]([O-])=O)cc1

InChI key

YAEMHJKFIIIULI-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

solid

color

off-white to tan

solubility

DMSO: ≥20 mg/mL, clear, light yellow, H2O: insoluble

originator

AstraZeneca

storage temp.

2-8°C

Quality Level

100

Related Categories

General description

AR-A014418 may have chronic pain-relieving properties. In mice having neuropathic pain, this molecule has been shown to have antihyperalgesic effects. AR-A014418 may modulate proinflammatory cytokines and the catecholaminergic and serotonergic pathways. It has also been studied that AR-A014418 inhibits growth of pancreatic cancer cells.

Application

AR-A014418 has been used as an inhibitor of glycogen synthase kinase 3 (GSK3).

Biochem/physiol Actions

AR-A014418 is a glycogen synthase kinase 3 (GSK3) inhibitor.
Glycogen synthase kinase 3 (GSK3) is a serine/threonine kinase that has been implicated in pathological conditions such as diabetes and Alzheimer′s disease. GSK3 inhibitor, AR-A014418, inhibits GSK3 (IC50 = 104 nM), in an ATP-competitive manner (Ki = 38 nM). AR-A014418 does not significantly inhibit cdk2 or cdk5 (IC50 > 100 μM) or 26 other kinases, demonstrating high specificity for GSK3.

Features and Benefits

This compound is featured on the PKB/Akt page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by AstraZeneca. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000164383
0000164384
0000164384
0000164383
0000120164

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Po-Hung Hsu et al.
Scientific reports, 8(1), 12882-12882 (2018-08-29)
Alzheimer's disease (AD) is a neurodegenerative disease that is the leading cause of age-related dementia. Currently, therapeutic agent delivery to the CNS is a valued approach for AD therapy. Unfortunately, the CNS penetration is greatly hampered by the blood-brain barrier
Miyuki Yoshiya et al.
Frontiers in neural circuits, 7, 191-191 (2013-12-19)
Modulation of synapses under acute stress is attracting much attention. Exposure to acute stress induces corticosterone (CORT) secretion from the adrenal cortex, resulting in rapid increase of CORT levels in plasma and the hippocampus. We tried to test whether rapid
Shadi Mamaghani et al.
PloS one, 7(7), e41102-e41102 (2012-07-26)
Tumor necrosis factor-related apoptosis inducing ligand (TRAIL) induces apoptosis in a variety of cancer cell lines with little or no effect on normal cells. However, its effect is limited as some cancers including pancreatic cancer show de novo resistance to
Glycogen synthase kinase 3-specific inhibitor AR-A014418 decreases neuropathic pain in mice: evidence for the mechanisms of action
Mazzardo-Martins L, et al.
Neuroscience, 226, 411-420 (2012)
Huilan Xie et al.
Journal of dental sciences, 17(2), 802-810 (2022-06-28)
Glycogen synthase kinase-3β (GSK3β) inhibitor enhances bone formation, while dental pulp stem cells (DPSC) are potentially used to repair bone defects. The present study aimed to investigate the effect of AR-A014418 (AR, a specific glycogen synthase kinase-3β inhibitor) on the
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