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D1692

GW4869

Name: GW4869
Brand: SIGMA

≥90% (NMR), powder, N-SMase inhibitor

Synonym(s):

N,N′-Bis[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-3,3′-p-phenylene-bis-acrylamide dihydrochloride

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About This Item

Empirical Formula (Hill Notation):

C₃₀H₂₈N₆O₂· 2HCl

CAS Number:

6823-69-4

Molecular Weight:

577.50

UNSPSC Code:

41121800

PubChem Substance ID:

24724460

NACRES:

NA.77

Assay:

≥90% (NMR)

Form:

powder

Quality level:

100

Storage condition:

desiccated, protect from light

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Properties

Product Name

GW4869, ≥90% (NMR)

Quality Level

100

assay

≥90% (NMR)

form

powder

storage condition

desiccated, protect from light

color

light yellow to yellow

mp

>300 °C

solubility

DMSO: 0.2 mg/mL

originator

GlaxoSmithKline

storage temp.

2-8°C

SMILES string

Cl.Cl.O=C(Nc1ccc(cc1)C2=NCCN2)\C=C/c3ccc(\C=C/C(=O)Nc4ccc(cc4)C5=NCCN5)cc3

InChI

1S/C30H28N6O2.2ClH/c37-27(35-25-11-7-23(8-12-25)29-31-17-18-32-29)15-5-21-1-2-22(4-3-21)6-16-28(38)36-26-13-9-24(10-14-26)30-33-19-20-34-30;;/h1-16H,17-20H2,(H,31,32)(H,33,34)(H,35,37)(H,36,38);2*1H/b15-5-,16-6-;;

InChI key

NSFKAZDTKIKLKT-LOLTXFFGSA-N

Description

General description

GW4869 is a commonly used pharmacological agent, which inhibits exosome generation. It blocks ceramide-mediated inward budding of multivesicular bodies (MVBs) and the release of mature exosomes from MVBs. GW4869 exhibits cytotoxicity to phosphatidylserine-expressing myeloma cells. It inhibits the secretion of IFN (interferon)-α by plasmacytoid dendritic cells (pDCs).

Application

GW4869 has been used:

as an inhibitor of neutral sphingomyelinase and exosome biogenesis
to analyse the effects of arsenic trioxide (ATO) treatment for hepatoma carcinoma HCCLM3 cells on ceramide production
to determine the contributions of p75 neurotrophin receptor (p75^NTR) and tropomyosin receptor kinase A (TrkA)- coupled pathways to nerve growth factor (NGF)-induced thermal hypersensitivity in rats

Biochem/physiol Actions

A cell-permeable, potent, specific, non-competitive inhibitor of N-SMase (neutral sphingomyelinase)

Features and Benefits

This compound was developed by GlaxoSmithKline. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Elevated Wall Tension Leads to Reduced miR-133a in the Thoracic Aorta by Exosome Release

Akerman AW, et al.

Journal of the American Heart Association, 8(1), e010332-e010332 (2019)

The TrkA receptor mediates experimental thermal hyperalgesia produced by nerve growth factor: modulation by the p75 neurotrophin receptor

Khodorova A, et al.

Neuroscience, 340, 384-397 (2017)

The cationic small molecule GW 4869 is cytotoxic to high phosphatidylserine-expressing myeloma cells

Vuckovic S, et al.

British Journal of Haematology, 177(3), 423-440 (2017)

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