Tamatinib free basefeatured
WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#:205926
CAS#:841290-80-0 (free base)
Description:Tamatinib, also known as R406, is a potent inhibitor of immunoglobulin E (IgE)- and IgG-mediated activation of Fc receptor signaling (EC(50) for degranulation = 56-64 nM). The primary target for R406 is the spleen tyrosine kinase (Syk). R406 inhibited phosphorylation of Syk substrate linker for activation of T cells in mast cells and B-cell linker protein/SLP65 in B cells. R406 bound to the ATP binding pocket of Syk and inhibited its kinase activity as an ATP-competitive inhibitor (K(i) = 30 nM).
Price and Availability
Tamatinib free base, purity > 98%, is in stock. The same day shipping after order is received.
Chemical Structure
Theoretical Analysis
MedKoo Cat#: 205926Name: Tamatinib free baseCAS#: 841290-80-0 (free base)Chemical Formula: C22H23FN6O5Exact Mass: 470.1714Molecular Weight: 470.45Elemental Analysis: C, 56.17; H, 4.93; F, 4.04; N, 17.86; O, 17.00
Related CAS #:841290-81-1 (besylate)841290-80-0 (free base)
Synonym:R 406, R406, R406, Tamatinib
IUPAC/Chemical Name:6-((5-fluoro-2-((3,4,5-trimethoxyphenyl)amino)pyrimidin-4-yl)amino)-2,2-dimethyl-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one
InChi Key:NHHQJBCNYHBUSI-UHFFFAOYSA-N
InChi Code: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)
SMILES Code:O=C1NC2=NC(NC3=NC(NC4=CC(OC)=C(OC)C(OC)=C4)=NC=C3F)=CC=C2OC1(C)C
Technical Data
References
1: Lhermusier T, van Rottem J, Garcia C, Xuereb JM,Ragab A, Martin V, Gratacap MP, Sié P, Payrastre B. The Syk-kinaseinhibitor R406 impairs platelet activation and monocyte tissue factorexpression triggered by heparin-PF4 complex directed antibodies. JThromb Haemost. 2011 Oct;9(10):2067-76. doi:10.1111/j.1538-7836.2011.04470.x. PubMed PMID: 21848694.
2: Sweeny DJ, Li W, Grossbard E, Lau DT. Contribution of gut bacteria tothe metabolism of the spleen tyrosine kinase (Syk) inhibitor R406 incynomolgus monkey. Xenobiotica. 2010 Jun;40(6):415-23. doi:10.3109/00498251003734244. PubMed PMID: 20415544.
3: Sweeny DJ, Li W, Clough J, Bhamidipati S, Singh R, Park G, Baluom M,Grossbard E, Lau DT. Metabolism of fostamatinib, the oral methylenephosphate prodrug of the spleen tyrosine kinase inhibitor R406 inhumans: contribution of hepatic and gut bacterial processes to theoverall biotransformation. Drug Metab Dispos. 2010 Jul;38(7):1166-76.doi: 10.1124/dmd.110.032151. Epub 2010 Apr 6. PubMed PMID: 20371637.
4: Quiroga MP, Balakrishnan K, Kurtova AV, Sivina M, Keating MJ, WierdaWG, Gandhi V, Burger JA. B-cell antigen receptor signaling enhanceschronic lymphocytic leukemia cell migration and survival: specifictargeting with a novel spleen tyrosine kinase inhibitor, R406. Blood.2009 Jul 30;114(5):1029-37. doi: 10.1182/blood-2009-03-212837. Epub 2009Jun 2. PubMed PMID: 19491390.
5: Spalton JC, Mori J, Pollitt AY, Hughes CE, Eble JA, Watson SP. Thenovel Syk inhibitor R406 reveals mechanistic differences in theinitiation of GPVI and CLEC-2 signaling in platelets. J Thromb Haemost.2009 Jul;7(7):1192-9. doi: 10.1111/j.1538-7836.2009.03451.x. Epub 2009Apr 24. PubMed PMID: 19422460.
6: Zhu Y, Herlaar E, Masuda ES, Burleson GR, Nelson AJ, Grossbard EB,Clemens GR. Immunotoxicity assessment for the novel Spleen tyrosinekinase inhibitor R406. Toxicol Appl Pharmacol. 2007 Jun15;221(3):268-77. Epub 2007 Mar 31. PubMed PMID: 17490694.
7: Braselmann S, Taylor V, Zhao H, Wang S, Sylvain C, Baluom M, Qu K,Herlaar E, Lau A, Young C, Wong BR, Lovell S, Sun T, Park G, Argade A,Jurcevic S, Pine P, Singh R, Grossbard EB, Payan DG, Masuda ES. R406, anorally available spleen tyrosine kinase inhibitor blocks fc receptorsignaling and reduces immune complex-mediated inflammation. J PharmacolExp Ther. 2006 Dec;319(3):998-1008. Epub 2006 Aug 31. PubMed PMID:16946104.
