gilteritinib   Click here for help

GtoPdb Ligand ID: 8708

Synonyms: ASP-2215 | ASP2215 | Xospata®
Approved drug PDB Ligand
gilteritinib is an approved drug (FDA (2018), EMA (2019))
Compound class: Synthetic organic
Comment: Gilteritinib is an orally bioavailable inhibitor of the receptor tyrosine kinases (RTKs) FMS-related tyrosine kinase 3 (FLT3), AXL and anaplastic lymphoma kinase (ALK) [4], with clinical antineoplastic activity. Gilteritinib inhibits the activity of FLT3-activating mutations which are one of the most common genetic alterations in acute myeloid leukemia (AML).

SARS-CoV-2: AXL is a kinase upstream of p38 MAP kinases. p38 activity has been reported to be upregulated following SARS-CoV-2 infection of host cells in vitro, and gilteritinib produces an antiviral effect (IC50= 807 nM) [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 10
Hydrogen bond donors 3
Rotatable bonds 9
Topological polar surface area 121.11
Molecular weight 552.35
XLogP 2.44
No. Lipinski's rules broken 0
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Canonical SMILES COc1cc(ccc1N1CCC(CC1)N1CCN(CC1)C)Nc1nc(NC2CCOCC2)c(nc1C(=O)N)CC
Isomeric SMILES COc1cc(ccc1N1CCC(CC1)N1CCN(CC1)C)Nc1nc(NC2CCOCC2)c(nc1C(=O)N)CC
InChI InChI=1S/C29H44N8O3/c1-4-23-28(31-20-9-17-40-18-10-20)34-29(26(33-23)27(30)38)32-21-5-6-24(25(19-21)39-3)37-11-7-22(8-12-37)36-15-13-35(2)14-16-36/h5-6,19-20,22H,4,7-18H2,1-3H3,(H2,30,38)(H2,31,32,34)
1. Bouhaddou M, Memon D, Meyer B, White KM, Rezelj VV, Marrero MC, Polacco BJ, Melnyk JE, Ulferts S, Kaake RM. (2020)
The Global Phosphorylation Landscape of SARS-CoV-2 Infection.
Cell, Article Online Now. DOI: 10.1016/j.cell.2020.06.034
2. EMA. 
Gilteritinib orphan designation.
Accessed on 15/04/2019. Modified on 15/04/2019. EMA,
3. EMA. 
Xospata: CHMP summary of opinion.
Accessed on 24/09/2019. Modified on 24/09/2019. European Medicines Agency,
4. Lee LY, Hernandez D, Rajkhowa T, Smith SC, Raman JR, Nguyen B, Small D, Levis M. (2017)
Preclinical studies of gilteritinib, a next-generation FLT3 inhibitor.
Blood, 129 (2): 257-260. [PMID:27908881]
5. Perl AE, Altman JK, Cortes J, Smith C, Litzow M, Baer MR, Claxton D, Erba HP, Gill S, Goldberg S et al.. (2017)
Selective inhibition of FLT3 by gilteritinib in relapsed or refractory acute myeloid leukaemia: a multicentre, first-in-human, open-label, phase 1-2 study.
Lancet Oncol, 18 (8): 1061-1075. [PMID:28645776]