Alisertib

Alisertib (MLN8237) is an orally available selective aurora A kinase inhibitor developed by Takeda.[1] It was investigated as a treatment for relapsed or refractory peripheral T-cell lymphoma.[2][3] Development was abandoned in 2015 due to poor clinical trial results.[4]

Alisertib
Names
Preferred IUPAC name
4-{[9-Chloro-7-(2-fluoro-6-methoxyphenyl)-5H-pyrimido[5,4-d][2]benzazepin-2-yl]amino}-2-methoxybenzoic acid
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
InChI
  • InChI=1S/C27H20ClFN4O4/c1-36-21-5-3-4-20(29)23(21)25-19-10-15(28)6-8-17(19)24-14(12-30-25)13-31-27(33-24)32-16-7-9-18(26(34)35)22(11-16)37-2/h3-11,13H,12H2,1-2H3,(H,34,35)(H,31,32,33)
    Key: ZLHFILGSQDJULK-UHFFFAOYSA-N
  • InChI=1/C27H20ClFN4O4/c1-36-21-5-3-4-20(29)23(21)25-19-10-15(28)6-8-17(19)24-14(12-30-25)13-31-27(33-24)32-16-7-9-18(26(34)35)22(11-16)37-2/h3-11,13H,12H2,1-2H3,(H,34,35)(H,31,32,33)
    Key: ZLHFILGSQDJULK-UHFFFAOYAB
SMILES
  • COC1=C(C(=CC=C1)F)C2=NCC3=CN=C(N=C3C4=C2C=C(C=C4)Cl)NC5=CC(=C(C=C5)C(=O)O)OC
Properties
Chemical formula
C27H20ClFN4O4
Molar mass 518.93 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References

  1. Friedberg, JW; Mahadevan, D; Cebula, E; Persky, D; Lossos, I; Agarwal, AB; Jung, J; Burack, R; Zhou, X; Leonard, EJ; Fingert, H; Danaee, H; Bernstein, SH (Jan 1, 2014). "Phase II study of alisertib, a selective Aurora A kinase inhibitor, in relapsed and refractory aggressive B- and T-cell non-Hodgkin lymphomas". Journal of Clinical Oncology. 32 (1): 44–50. doi:10.1200/JCO.2012.46.8793. PMC 3867644. PMID 24043741.
  2. "Millennium Initiates Pivotal Phase 3 Trial of MLN8237 in Patients With Relapsed or Refractory Peripheral T-cell Lymphoma". Takeda Pharmaceutical Company Limited; Millennium Pharmaceuticals, Inc. March 6, 2012. Retrieved 20 March 2014.
  3. "Research and Development Pipeline (As of February 5, 2014)" (PDF). Takeda Pharmaceutical Company Limited. February 5, 2014. p. 2. Retrieved 20 March 2014.
  4. "Takeda Announces Termination of Alisertib Phase 3 Trial in Relapsed or Refractory Peripheral T-cell Lymphoma".
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