fostamatinib   Click here for help

GtoPdb Ligand ID: 7796

Synonyms: R 788 | R-788 | R7935788 | Tavalisse® | Tavlesse®
Approved drug PDB Ligand Immunopharmacology Ligand
fostamatinib is an approved drug (FDA (2018), EMA (2020))
Compound class: Synthetic organic
Comment: Fostamatinib is a spleen tyrosine kinase (Syk) inhibitor prodrug. Fostamatinib is administered orally in disodium salt preparations (e.g. PubChem CID 25008120 and fostamatinib disodium hexahydrate CID 24828759). It is rapidly converted to tamatinib by alkaline phosphatases in intestinal enterocytes [6]. Although development in rheumatoid arthritis was discontinued in 2013 due to a lack of observed efficacy, development continued in patients with chronic and persistent immune thrombocytopenia (ITP).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 11
Hydrogen bond donors 4
Rotatable bonds 10
Topological polar surface area 196.53
Molecular weight 580.15
XLogP 1.06
No. Lipinski's rules broken 1
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Canonical SMILES COc1cc(Nc2ncc(c(n2)Nc2ccc3c(n2)N(COP(=O)(O)O)C(=O)C(O3)(C)C)F)cc(c1OC)OC
Isomeric SMILES COc1cc(Nc2ncc(c(n2)Nc2ccc3c(n2)N(COP(=O)(O)O)C(=O)C(O3)(C)C)F)cc(c1OC)OC
InChI InChI=1S/C23H26FN6O9P/c1-23(2)21(31)30(11-38-40(32,33)34)20-14(39-23)6-7-17(28-20)27-19-13(24)10-25-22(29-19)26-12-8-15(35-3)18(37-5)16(9-12)36-4/h6-10H,11H2,1-5H3,(H2,32,33,34)(H2,25,26,27,28,29)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2018), EMA (2020))
Is prodrug? Yes
Active form tamatinib
IUPAC Name Click here for help
[6-[[5-fluoro-2-[(3,4,5-trimethoxyphenyl)amino]pyrimidin-4-yl]amino]-2,2-dimethyl-3-oxopyrido[2,3-e][1,4]oxazin-4-yl]methyl dihydrogen phosphate
International Nonproprietary Names Click here for help
INN number INN
9022 fostamatinib
Synonyms Click here for help
R 788 | R-788 | R7935788 | Tavalisse® | Tavlesse®
Database Links Click here for help
CAS Registry No. 901119-35-5
ChEMBL Ligand CHEMBL2103830
DrugCentral Ligand 5280
GtoPdb PubChem SID 223366127
PubChem CID 11671467
Search Google for chemical match using the InChIKey GKDRMWXFWHEQQT-UHFFFAOYSA-N
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UniChem Compound Search for chemical match using the InChIKey GKDRMWXFWHEQQT-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey GKDRMWXFWHEQQT-UHFFFAOYSA-N
Wikipedia Fostamatinib