fenebrutinib   Click here for help

GtoPdb Ligand ID: 9299

Synonyms: Example 130 [US20140194408] | GDC-0853 | GDC0853 | RG-7845 | RG7845
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Fenebrutinib (RG7845, GDC-0853) is a Bruton's tyrosine kinase (BTK) inhibitor, under investigation for therapeutic potential in difficult-to-treat autoimmune diseases. The compound is claimed in patent WO2013067274 [2].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 10
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 120.99
Molecular weight 664.35
XLogP 5.44
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES OCc1c(ccnc1N1CCn2c(C1=O)cc1c2CC(C1)(C)C)c1cc(Nc2ccc(cn2)N2CCN(CC2C)C2COC2)c(=O)n(c1)C
Isomeric SMILES OCc1c(ccnc1N1CCn2c(C1=O)cc1c2CC(C1)(C)C)c1cc(Nc2ccc(cn2)N2CCN(C[C@@H]2C)C2COC2)c(=O)n(c1)C
InChI InChI=1S/C37H44N8O4/c1-23-18-42(27-21-49-22-27)9-10-43(23)26-5-6-33(39-17-26)40-30-13-25(19-41(4)35(30)47)28-7-8-38-34(29(28)20-46)45-12-11-44-31(36(45)48)14-24-15-37(2,3)16-32(24)44/h5-8,13-14,17,19,23,27,46H,9-12,15-16,18,20-22H2,1-4H3,(H,39,40)/t23-/m0/s1
InChI Key WNEODWDFDXWOLU-QHCPKHFHSA-N
References
1. Akinleye A, Chen Y, Mukhi N, Song Y, Liu D. (2013)
Ibrutinib and novel BTK inhibitors in clinical development.
J Hematol Oncol, 6: 59. [PMID:23958373]
2. Crawford JJ, Ortwine DF, Wei B, Young WB. (2013)
Heteroaryl pyridone and aza-pyridone compounds as inhibitors of btk activity.
Patent number: WO2013067274. Assignee: Genentech, Inc.. Priority date: 03/11/2011. Publication date: 10/05/2013.
3. Musumeci F, Sanna M, Greco C, Giacchello I, Fallacara AL, Amato R, Schenone S. (2017)
Pyrrolo[2,3-d]pyrimidines active as Btk inhibitors.
Expert Opin Ther Pat, 27 (12): 1305-1318. [PMID:28705083]