crenolanib   Click here for help

GtoPdb Ligand ID: 7882

Synonyms: ARO-002 | CP 868596 | CP-868,596 | CP-868596
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Crenolanib (CP-868,596) is a potent and orally bioavailable benzamidazole Type I inhibitor of wild-type and mutant isoforms of the class III receptor tyrosine kinases FLT3 (FMS-like tyrosine kinase 3), PDGFRα (platelet-derived growth factor receptor), and PDGFRβ [1-3]. It preferentially binds to phosphorylated active kinases in the 'DFG in' conformation.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 77.91
Molecular weight 443.23
XLogP 4.26
No. Lipinski's rules broken 0
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Canonical SMILES NC1CCN(CC1)c1cccc2c1nc(cc2)n1cnc2c1ccc(c2)OCC1(C)COC1
Isomeric SMILES NC1CCN(CC1)c1cccc2c1nc(cc2)n1cnc2c1ccc(c2)OCC1(C)COC1
InChI InChI=1S/C26H29N5O2/c1-26(14-32-15-26)16-33-20-6-7-22-21(13-20)28-17-31(22)24-8-5-18-3-2-4-23(25(18)29-24)30-11-9-19(27)10-12-30/h2-8,13,17,19H,9-12,14-16,27H2,1H3
1. Heinrich MC, Griffith D, McKinley A, Patterson J, Presnell A, Ramachandran A, Debiec-Rychter M. (2012)
Crenolanib inhibits the drug-resistant PDGFRA D842V mutation associated with imatinib-resistant gastrointestinal stromal tumors.
Clin Cancer Res, 18 (16): 4375-84. [PMID:22745105]
2. Smith CC, Lasater EA, Lin KC, Wang Q, McCreery MQ, Stewart WK, Damon LE, Perl AE, Jeschke GR, Sugita M et al.. (2014)
Crenolanib is a selective type I pan-FLT3 inhibitor.
Proc Natl Acad Sci USA, 111 (14): 5319-24. [PMID:24623852]
3. Zimmerman EI, Turner DC, Buaboonnam J, Hu S, Orwick S, Roberts MS, Janke LJ, Ramachandran A, Stewart CF, Inaba H et al.. (2013)
Crenolanib is active against models of drug-resistant FLT3-ITD-positive acute myeloid leukemia.
Blood, 122 (22): 3607-15. [PMID:24046014]