2RC

[6-({5-fluoro-2-[(3,4,5-trimethoxyphenyl)amino]pyrimidin-4-yl}amino)-2,2-dimethyl-3-oxo-2,3-dihydro-4H-pyrido[3,2-b][1,4]oxazin-4-yl]methyl dihydrogen phosphate

Created: 2014-01-13
Last modified:  2021-03-01

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Chemical Details

Formal Charge0
Atom Count66
Chiral Atom Count0
Bond Count69
Aromatic Bond Count18
2D diagram of 2RC
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Chemical Component Summary

Name[6-({5-fluoro-2-[(3,4,5-trimethoxyphenyl)amino]pyrimidin-4-yl}amino)-2,2-dimethyl-3-oxo-2,3-dihydro-4H-pyrido[3,2-b][1,4]oxazin-4-yl]methyl dihydrogen phosphate
SynonymsFostamatinib
Systematic Name (OpenEye OEToolkits)[6-[[5-fluoranyl-2-[(3,4,5-trimethoxyphenyl)amino]pyrimidin-4-yl]amino]-2,2-dimethyl-3-oxidanylidene-pyrido[3,2-b][1,4]oxazin-4-yl]methyl dihydrogen phosphate
FormulaC23 H26 F N6 O9 P
Molecular Weight580.46
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01Fc1cnc(nc1Nc2nc3N(C(=O)C(Oc3cc2)(C)C)COP(=O)(O)O)Nc4cc(OC)c(OC)c(OC)c4
SMILESCACTVS3.385COc1cc(Nc2ncc(F)c(Nc3ccc4OC(C)(C)C(=O)N(CO[P](O)(O)=O)c4n3)n2)cc(OC)c1OC
SMILESOpenEye OEToolkits1.7.6CC1(C(=O)N(c2c(ccc(n2)Nc3c(cnc(n3)Nc4cc(c(c(c4)OC)OC)OC)F)O1)COP(=O)(O)O)C
Canonical SMILESCACTVS3.385 COc1cc(Nc2ncc(F)c(Nc3ccc4OC(C)(C)C(=O)N(CO[P](O)(O)=O)c4n3)n2)cc(OC)c1OC
Canonical SMILESOpenEye OEToolkits1.7.6 CC1(C(=O)N(c2c(ccc(n2)Nc3c(cnc(n3)Nc4cc(c(c(c4)OC)OC)OC)F)O1)COP(=O)(O)O)C
InChIInChI1.03 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)
InChIKeyInChI1.03 GKDRMWXFWHEQQT-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank IDDB12010 
NameFostamatinib
Groups
  • approved
  • investigational
DescriptionFostamatinib has been investigated for the treatment and basic science of Rheumatoid Arthritis and Immune Thrombocytopenic Purpura (ITP). It was approved on April 17, 2018, under the trade name Tavalisse for use in ITP [L2644, FDA Label]. Fostamatinib has also been granted orphan drug status by the FDA [L2644]. Recently, fostamatinib has been identified as a potential therapeutic for controlling acute respiratory distress syndrome (ARDS) in patients with severe COVID-19 through its ability to modulate the SYK kinase.[A235008, A235013, A235018]
Synonyms
  • Fostamatinib disodium
  • Fostamatinib
Brand Names
  • Tavalisse
  • Tavlesse
IndicationFostamatinib is indicated for use in the treatment of chronic immune thrombocytopenia (ITP) in patients who have had insufficient response to previous therapy [FDA Label].
Categories
  • Amines
  • BCRP/ABCG2 Inhibitors
  • Blood and Blood Forming Organs
  • Cytochrome P-450 CYP3A Inhibitors
  • Cytochrome P-450 CYP3A Substrates
ATC-CodeB02BX09
CAS number901119-35-5

Drug Targets

NameTarget SequencePharmacological ActionActions
Tyrosine-protein kinase SYKMASSGMADSANHLPFFFGNITREEAEDYLVQGGMSDGLYLLRQSRNYLGG...unknowninhibitor
Adenosine receptor A3MPNNSTALSLANVTYITMEIFIGLCAIVGNVLVICVVKLNPSLQTTTFYF...unknownantagonist
Synaptic vesicular amine transporterMALSELALVRWLQESRRSRKLILFIVFLALLLDNMLLTVVVPIIPSYLYS...unknowninhibitor
Fatty-acid amide hydrolase 1MVQYELWAALPGASGVALACCFVAAAVALRWSGRRTARGAVVRARQRQRA...unknowninhibitor
Equilibrative nucleoside transporter 1MTTSHQPQDRYKAVWLIFFMLGLGTLLPWNFFMTATQYFTNRLDMSQNVS...unknowninhibitor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL2103830
PubChem 11671467
ChEMBL CHEMBL2103830