A benzimidazole
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IRAK1/4 Inhibitor

Item No. 17540

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[1-[2-(4-morpholinyl)ethyl]-1H-benzimidazol-2-yl]-3-nitro-benzamide
CAS Number
509093-47-4
Synonyms
  • IL-1 Receptor-associated Kinase 1/4 Inhibitor
  • Interleukin-1 Receptor-associated Kinase 1/4 Inhibitor
Molecular Formula
C20H21N5O4
Formula Weight
395.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 0.5 mg/mlDMSO: 1 mg/ml
λmax
224, 259, 322 nm
SMILES
O=C(C1=CC([N+]([O-])=O)=CC=C1)NC2=NC3=CC=CC=C3N2CCN4CCOCC4
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Interleukin-1 receptor-associated kinases (IRAKs) are important mediators in the signal transduction of Toll/IL-1 receptor (TIR) family members. Dysregulation of TIR signaling, typified by increased NF-κB activity, results in the development of some cancers and other diseases, making the development of IRAK inhibitors a potential therapeutic strategy. IRAK1/4 inhibitor is a benzimidazole that disrupts the activity of IRAK 1 and 4 with IC50 values of 0.3 and 0.2 µM, respectively.1 It demonstrates IC50 values >10 µM in a panel of 27 other kinases tested.1 This compound has been used to inhibit a pro-inflammatory response in microglia isolated from clinically diagnosed Alzheimer’s disease patients.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Powers, J.P., Li, S., Jaen, J.C., et al. Discovery and initial SAR of inhibitors of interleukin-1 receptor-associated kinase-4. Bioorg. Med. Chem. Lett. 16(11), 2842-2845 (2006).

    2. Hoozemans, J.J.M., van Haastert, E.S., Mulder, S.D., et al. Increased IRAK-4 kinase activity in Alzheimer’s disease; IRAK-¼ inhibitor I prevents pro-inflammatory cytokine secretion but not the uptake of amyloid beta by primary human glia. J. Clin. Cell. Immunol. 5, (2014).