Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

I5409

Sigma-Aldrich

IRAK-1/4 Inhibitor I

≥98% (HPLC), solid

Synonym(s):

1-(2-(4-Morpholinyl)ethyl)-2-(3-nitrobenzoylamino)benzimidazole, N-(2-Morpholinylethyl)-2-(3-nitrobenzoylamido)-benzimidazole

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C20H21N5O4
CAS Number:
509093-47-4
Molecular Weight:
395.41
MDL number:
MFCD09752602
UNSPSC Code:
51111800
PubChem Substance ID:
329815384
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

solid

color

off-white to light yellow

solubility

DMSO: ≥5 mg/mL

storage temp.

2-8°C

SMILES string

O=C(C1=CC([N+]([O-])=O)=CC=C1)NC2=NC3=C(N2CCN4CCOCC4)C=CC=C3

InChI

1S/C20H21N5O4/c26-19(15-4-3-5-16(14-15)25(27)28)22-20-21-17-6-1-2-7-18(17)24(20)9-8-23-10-12-29-13-11-23/h1-7,14H,8-13H2,(H,21,22,26)

InChI key

QTCFYQHZJIIHBS-UHFFFAOYSA-N

Application

IRAK-1/4 inhibitor I has been used in various studies to inhibit IRAK1 in hepatoma cell lines and head and neck squamous cell carcinoma (HNSCC) cell lines.

Biochem/physiol Actions

IRAK-1/4 Inhibitor I is a novel benzimidazole that is a potent inhibitor of interleukin-1 receptor-associated kinases 1/4 (IRAK 1/4). IC50 values were 300 nM and 200 nM for IRAK-1 and -4, respectively, and >10,000 nM for a panel of 27 other kinases tested.
IRAK1 overexpression leads to the development of head and neck squamous cell carcinoma (HNSCC). Therefore, IRAK-1/4 inhibitor I might be a potential therapeutic for HNSCC tumors. Various experimental studies states that IRAK-1/4 inhibitor might have a potential to exhibit inhibitory effects on the nuclear factor (NF)-κB signaling pathway.

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Federica Agliano et al.
Scientific reports, 10(1), 12100-12100 (2020-07-23)
Sterile stimuli can trigger inflammatory responses, and in some cases can lead to a variety of acute or chronic diseases. In this study, we hypothesize that a benzimidazole inhibitor may be used as a therapeutic in the treatment of sterile inflammation.
Targeting interleukin-1 receptor-associated kinase 1 for human hepatocellular carcinoma
Li N, et al.
Journal of Experimental & Clinical Cancer Research, 35(1), 140-140 (2016)
The Impact of Inflammation-Induced Tumor Plasticity during Myeloid Transformation.
Yeaton, et al.
Cancer Discovery, 12, 2392-2413 (2023)
Mostafa Allahyari et al.
Asian biomedicine : research, reviews and news, 14(6), 253-260 (2020-12-31)
Obesity and the inflammation associated with it, play a key role in the development of insulin resistance through the release of inflammatory cytokines and free fatty acids and the stimulation of toll-like receptors (TLR). Interleukin-1 receptor-associated kinase (IRAK), which mediates
IRAK1 is a novel DEK transcriptional target and is essential for head and neck cancer cell survival
Adams AK, et al.
Oncotarget, 6(41), 43395-43395 (2015)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service