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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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)
InChI Key GKDRMWXFWHEQQT-UHFFFAOYSA-N
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
RCSB PDB Ligand 2RC
Search Google for chemical match using the InChIKey GKDRMWXFWHEQQT-UHFFFAOYSA-N
Search Google for chemicals with the same backbone GKDRMWXFWHEQQT
Search PubMed clinical trials fostamatinib
Search PubMed titles fostamatinib
Search PubMed titles/abstracts fostamatinib
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