Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

Safety Information

SML4053

Sigma-Aldrich

R406

new

≥98% (HPLC)

Synonym(s):

6-[[5-Fluoro-2-[(3,4,5-trimethoxyphenyl)amino]-4-pyrimidinyl]amino]-2,2-dimethyl-2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one, N4-(2,2-dimethyl-3-oxo-4H-pyrid[1,4]oxazin-6-yl)-5-fluoro-N2-(3,4,5-trimethoxyphenyl)-2,4-pyrimidinediamine, R 406 (free base), Tamatinib (free base)

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

About This Item

Empirical Formula (Hill Notation):
C22H23FN6O5
CAS Number:
841290-80-0
Molecular Weight:
470.45
MDL number:
MFCD27976370
UNSPSC Code:
12352200

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear (Warmed)

storage temp.

-10 to -25°C

SMILES string

CC1(C(NC2=C(O1)C=CC(NC3=NC(NC4=CC(OC)=C(C(OC)=C4)OC)=NC=C3F)=N2)=O)C

InChI

1S/C22H23FN6O5/c1-22(2)20(30)28-19-13(34-22)6-7-16(27-19)26-18-12(23)10-24-21(29-18)25-11-8-14(31-3)17(33-5)15(9-11)32-4/h6-10H,1-5H3,(H3,24,25,26,27,28,29,30)

InChI key

NHHQJBCNYHBUSI-UHFFFAOYSA-N

Biochem/physiol Actions

Orally available, potent, and selective ATP competitive inhibitor of Syk (spleen tyrosine kinase); TAK1 activator.
R406 (Tamatinib) is an orally available, potent, and selective ATP competitive inhibitor of Syk (spleen tyrosine kinase) activity (Ki= 30 nM). R406 potently induces apoptosis in cancer cells overexpressing Syk. R406 is the active metabolite of pro-drug Fostamatinib (R-788). R406 promotes the activation of TAK1 by direct binding to TAK1, independent of its original target Syk kinase.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

SML4053-10MG:
SML4053-50MG:
SML4053-VAR:
SML4053-BULK:

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000384476
0000384474
0000365478
0000365478
0000384476

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

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

Visit the Document Library

Hoon-Suk Cha et al.
The Journal of pharmacology and experimental therapeutics, 317(2), 571-578 (2006-02-03)
Spleen tyrosine kinase (Syk) is a key regulator of cell signaling induced by cytokines or Fc receptor engagement. However, the role of Syk in rheumatoid arthritis (RA) is not known yet. We investigated the pathways activated by Syk in tumor
Attila Mócsai et al.
Nature reviews. Immunology, 10(6), 387-402 (2010-05-15)
Spleen tyrosine kinase (SYK) is known to have a crucial role in adaptive immune receptor signalling. However, recent reports indicate that SYK also mediates other, unexpectedly diverse biological functions, including cellular adhesion, innate immune recognition, osteoclast maturation, platelet activation and
Weimin Sun et al.
Proceedings of the National Academy of Sciences of the United States of America, 120(39), e2308079120-e2308079120 (2023-09-21)
TAK1 is a key modulator of both NF-κB signaling and RIPK1. In TNF signaling pathway, activation of TAK1 directly mediates the phosphorylation of IKK complex and RIPK1. In a search for small molecule activators of RIPK1-mediated necroptosis, we found R406/R788

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