glasdegib   Click here for help

GtoPdb Ligand ID: 8201

Synonyms: Daurismo® | PF 04449913 | PF-04449913
Approved drug
glasdegib is an approved drug (FDA (2018), EMA (2020))
Compound class: Synthetic organic
Comment: Glasdegib is a potent and orally active inhibitor of the hedgehog signalling pathway, that acts as an antagonist of the class frizzled GPCR, smoothened (SMO) [2].
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 6
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 96.84
Molecular weight 374.19
XLogP 2.15
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES N#Cc1ccc(cc1)NC(=O)NC1CCN(C(C1)c1nc2c([nH]1)cccc2)C
Isomeric SMILES N#Cc1ccc(cc1)NC(=O)N[C@@H]1CCN([C@H](C1)c1nc2c([nH]1)cccc2)C
InChI InChI=1S/C21H22N6O/c1-27-11-10-16(24-21(28)23-15-8-6-14(13-22)7-9-15)12-19(27)20-25-17-4-2-3-5-18(17)26-20/h2-9,16,19H,10-12H2,1H3,(H,25,26)(H2,23,24,28)/t16-,19-/m1/s1
1. Cortes JE, Douglas Smith B, Wang ES, Merchant A, Oehler VG, Arellano M, DeAngelo DJ, Pollyea DA, Sekeres MA, Robak T et al.. (2018)
Glasdegib in combination with cytarabine and daunorubicin in patients with AML or high-risk MDS: Phase 2 study results.
Am J Hematol, 93 (11): 1301-1310. [PMID:30074259]
2. Munchhof MJ, Li Q, Shavnya A, Borzillo GV, Boyden TL, Jones CS, LaGreca SD, Martinez-Alsina L, Patel N, Pelletier K et al.. (2012)
Discovery of PF-04449913, a Potent and Orally Bioavailable Inhibitor of Smoothened.
ACS Med Chem Lett, 3 (2): 106-11. [PMID:24900436]