Alisertib

Alisertib
Names
	IUPAC name 4-{[9-Chloro-7-(2-fluoro-6-methoxyphenyl)-5H-pyrimido[5,4-d][2]benzazepin-2-yl]amino}-2-methoxybenzoic acid
	Systematic 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	1028486-01-2;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL483158;
ChemSpider	24700147;
IUPHAR/BPS	7790;
KEGG	D10085;
PubChem CID	24771867;
UNII	T66ES73M18;
CompTox Dashboard (EPA)	DTXSID30145539 ;
	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

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]

References

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.
"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.
"Research and Development Pipeline (As of February 5, 2014)" (PDF). Takeda Pharmaceutical Company Limited. February 5, 2014. p. 2. Retrieved 20 March 2014.
https://www.takeda.com/newsroom/newsreleases/2015/takeda-announces-termination-of-alisertib-phase-3-trial-in-relapsed-or-refractory-peripheral-t-cell-lymphoma/

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[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] ttps://www.takeda.com/newsroom/newsreleases/2015/takeda-announces-termination-of-alisertib-phase-3-trial-in-relapsed-or-refractory-peripheral-t-cell-lymphoma/