ixazomib   Click here for help

GtoPdb Ligand ID: 8450

Synonyms: MLN-2238 | MLN2238 | Ninlaro®
Approved drug PDB Ligand
ixazomib is an approved drug (FDA (2015), EMA (2016))
Compound class: Synthetic organic
Comment: Ixazomib is the first approved oral proteasome inhibitor. Ixazomib reversibly inhibits 20S proteasome activity. Like bortezomib, ixazomib primarily inhibits the chymotrypsin-like (β5) proteolytic site within the 20S proteasome, but its pharmacokinetics, pharmacodynamics, and antitumor activity are superior to those of bortezomib [3].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 4
Rotatable bonds 9
Topological polar surface area 98.66
Molecular weight 360.08
XLogP 2.7
No. Lipinski's rules broken 0
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Canonical SMILES OB(C(NC(=O)CNC(=O)c1cc(Cl)ccc1Cl)CC(C)C)O
Isomeric SMILES OB([C@@H](NC(=O)CNC(=O)c1cc(Cl)ccc1Cl)CC(C)C)O
InChI InChI=1S/C14H19BCl2N2O4/c1-8(2)5-12(15(22)23)19-13(20)7-18-14(21)10-6-9(16)3-4-11(10)17/h3-4,6,8,12,22-23H,5,7H2,1-2H3,(H,18,21)(H,19,20)/t12-/m0/s1
Bioactivity Comments
Administered as ixazomib citrate (MLN9708, PubChem CID 56844015) which is rapidly hydrolysed to its biologically active boronic acid form (ixazomib, MLN2238). Preclinical studies have demonstrated antitumor activity in MM cell lines and xenograft models [4].
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
proteasome 20S subunit beta 5 Primary target of this compound Hs Inhibitor Inhibition 9.0 pKi - 3
pKi 9.0 (Ki 9.3x10-10 M) [3]