avadomide   Click here for help

GtoPdb Ligand ID: 10522

Synonyms: CC-122 | CC122 | Compound A [WO2014039960A1]
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Avadomide (CC-122) is a cereblon (CRBN)-targeting compound [2] that exhibits potent single-agent clinical antitumour and immunomodulatory activities [3]. It retains the glutarimide moiety that is shared by all thalidomide family drugs, and which is known to directly interact with CRBN. The INN record specifies avadomide as a racemic mixture of enantiomers. We show the structure without specified stereochemistry to represent the mixture. It is claimed as Compound A in Celgene's patent WO2014039960A1 [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 1
Topological polar surface area 107.08
Molecular weight 286.11
XLogP -0.04
No. Lipinski's rules broken 0
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Canonical SMILES O=C1CCC(C(=O)N1)n1c(C)nc2c(c1=O)c(N)ccc2
Isomeric SMILES O=C1CCC(C(=O)N1)n1c(C)nc2c(c1=O)c(N)ccc2
InChI InChI=1S/C14H14N4O3/c1-7-16-9-4-2-3-8(15)12(9)14(21)18(7)10-5-6-11(19)17-13(10)20/h2-4,10H,5-6,15H2,1H3,(H,17,19,20)
Immunopharmacology Comments
Avadomide promotes an immunostimulatory effect in primary T cells, which is effected via selective CUL4CRBN E3-mediated degradation of the lymphoid transcription factors Ikaros (IKZF1) and Aiolos (IKZF3) and subsequent elevation of IL-2 production [2].