sonidegib   

GtoPdb Ligand ID: 8199

Synonyms: erismodegib (deleted INN) | LDE-225 | LDE225 | NVP-LDE225 | Odomzo®
sonidegib is an approved drug (EMA & FDA (2015))
Compound class: Synthetic organic
Comment: Sonidegib (INN formerly erismodegib, but replaced in 2012) is an orally active inhibitor of the hedgehog signalling pathway, acting as an antagonist of the class frizzled GPCR, smoothened (SMO) [1-2].
The first hedgehog pathway inhibitor to be approved was vismodegib (2012).
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 63.69
Molecular weight 485.19
XLogP 6.86
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES CC1OC(C)CN(C1)c1ccc(cn1)NC(=O)c1cccc(c1C)c1ccc(cc1)OC(F)(F)F
Isomeric SMILES C[C@@H]1O[C@H](C)CN(C1)c1ccc(cn1)NC(=O)c1cccc(c1C)c1ccc(cc1)OC(F)(F)F
InChI InChI=1S/C26H26F3N3O3/c1-16-14-32(15-17(2)34-16)24-12-9-20(13-30-24)31-25(33)23-6-4-5-22(18(23)3)19-7-10-21(11-8-19)35-26(27,28)29/h4-13,16-17H,14-15H2,1-3H3,(H,31,33)/t16-,17+
InChI Key VZZJRYRQSPEMTK-CALCHBBNSA-N
References
1. Pan S, Wu X, Jiang J, Gao W, Wan Y, Cheng D, Han D, Liu J, Englund NP, Wang Y et al.. (2010)
Discovery of NVP-LDE225, a Potent and Selective Smoothened Antagonist.
ACS Med Chem Lett, 1 (3): 130-4. [PMID:24900187]
2. Wang J, Mook Jr RA, Lu J, Gooden DM, Ribeiro A, Guo A, Barak LS, Lyerly HK, Chen W. (2012)
Identification of a novel Smoothened antagonist that potently suppresses Hedgehog signaling.
Bioorg. Med. Chem., 20 (22): 6751-7. [PMID:23063522]