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
1. Bonvini P, Zorzi E, Basso G, Rosolen A. (2007)
Bortezomib-mediated 26S proteasome inhibition causes cell-cycle arrest and induces apoptosis in CD-30+ anaplastic large cell lymphoma.
Leukemia, 21 (4): 838-42. [PMID:17268529]
2. Ciechanover A. (2005)
Intracellular protein degradation: from a vague idea, through the lysosome and the ubiquitin-proteasome system, and onto human diseases and drug targeting (Nobel lecture).
Angew Chem Int Ed Engl, 44 (37): 5944-67. [PMID:16142822]
3. Kupperman E, Lee EC, Cao Y, Bannerman B, Fitzgerald M, Berger A, Yu J, Yang Y, Hales P, Bruzzese F et al.. (2010)
Evaluation of the proteasome inhibitor MLN9708 in preclinical models of human cancer.
Cancer Res, 70 (5): 1970-80. [PMID:20160034]
4. Richardson PG, Moreau P, Laubach JP, Gupta N, Hui AM, Anderson KC, San Miguel JF, Kumar S. (2015)
The investigational proteasome inhibitor ixazomib for the treatment of multiple myeloma.
Future Oncol, 11 (8): 1153-68. [PMID:25832873]