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A3230

Sigma-Aldrich

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
MDL number:
MFCD08277040
UNSPSC Code:
12352200
PubChem Substance ID:
329770820

Quality Level

100

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

SMILES string

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

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)

InChI key

YAEMHJKFIIIULI-UHFFFAOYSA-N

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

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 Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Qichen Hu et al.
ASN neuro, 4(5) (2012-05-26)
Signalling through the IGF1R [type 1 IGF (insulin-like growth factor) receptor] and canonical Wnt signalling are two signalling pathways that play critical roles in regulating neural cell generation and growth. To determine whether the signalling through the IGF1R can interact
Glycogen synthase kinase-3 inhibitor AR-A014418 suppresses pancreatic cancer cell growth via inhibition of GSK-3-mediated Notch1 expression
Selvi K, et al.
Hpb : the Official Journal of the International Hepato Pancreato Biliary Association, 17(9), 770-776 (2015)
Slava Rom et al.
The American journal of pathology, 181(4), 1414-1425 (2012-08-07)
Glycogen synthase kinase (GSK) 3β has been identified as a regulator of immune responses. We demonstrated previously that GSK3β inhibition in human brain microvascular endothelial cells (BMVECs) reduced monocyte adhesion/migration across BMVEC monolayers. Herein, we tested the idea that GSK3β
GSK3beta inhibition promotes synaptogenesis in Drosophila and mammalian neurons
Cuesto G, et al.
PLoS ONE, 10(3), e0118475-e0118475 (2015)
S Fittipaldi et al.
Journal of endocrinological investigation, 42(6), 727-739 (2018-11-28)
Cadmium (Cd) is a widespread environmental pollutant that causes alterations in human health acting as endocrine disruptor. Recent data suggest that cardiovascular system might be a contamination target tissue, since Cd is found in atheromatic plaques. Thus, the purpose of
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