Alisertib

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	1028486-01-2;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:125628;
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 , investigational, reversible, ATP-competitive, selective aurora A kinase inhibitor developed by Takeda.^[1] Inhibition of Aurora Kinase A leads to disruption of mitotic spindle apparatus assembly, disruption of chromosome segregation, and inhibition of cell proliferation.^[2] ^[3]

Takeda investigated alisertib as a treatment for relapsed or refractory peripheral T-cell lymphoma^[4]^[5] and development was paused in 2015^[6] till Puma Biotechnology licensed global rights to alisertib from Takeda in 2022. ^[7]^[8]

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.
^ Manfredi, Mark G.; Ecsedy, Jeffrey A.; Chakravarty, Arijit; Silverman, Lee; Zhang, Mengkun; Hoar, Kara M.; Stroud, Stephen G.; Chen, Wei; Shinde, Vaishali; Huck, Jessica J.; Wysong, Deborah R.; Janowick, David A.; Hyer, Marc L.; Leroy, Patrick J.; Gershman, Rachel E. (2011-12-15). "Characterization of Alisertib (MLN8237), an investigational small-molecule inhibitor of aurora A kinase using novel in vivo pharmacodynamic assays". Clinical Cancer Research: An Official Journal of the American Association for Cancer Research. 17 (24): 7614–7624. doi:10.1158/1078-0432.CCR-11-1536. ISSN 1557-3265. PMID 22016509.
^ Niu, Huifeng; Manfredi, Mark; Ecsedy, Jeffrey A. (2015-08-24). "Scientific Rationale Supporting the Clinical Development Strategy for the Investigational Aurora A Kinase Inhibitor Alisertib in Cancer". Frontiers in Oncology. 5: 189. doi:10.3389/fonc.2015.00189. ISSN 2234-943X. PMC 4547019. PMID 26380220.
^ "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.
^ "Takeda Announces Termination of Alisertib Phase 3 Trial in Relapsed or Refractory Peripheral T-cell Lymphoma".
^ Taylor, Nick Paul (September 21, 2022). "Puma pounces on failed Takeda drug, snapping up cancer prospect for knockdown price".{{cite news}}: CS1 maint: url-status (link)
^ Taylor, Phil (September 21, 2022). "Takeda farms out cancer drug alisertib to Puma Biotech".{{cite news}}: CS1 maint: url-status (link)

This article about an organic compound is a stub. You can help Wikipedia by expanding it.

[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] Manfredi, Mark G.; Ecsedy, Jeffrey A.; Chakravarty, Arijit; Silverman, Lee; Zhang, Mengkun; Hoar, Kara M.; Stroud, Stephen G.; Chen, Wei; Shinde, Vaishali; Huck, Jessica J.; Wysong, Deborah R.; Janowick, David A.; Hyer, Marc L.; Leroy, Patrick J.; Gershman, Rachel E. (2011-12-15). "Characterization of Alisertib (MLN8237), an investigational small-molecule inhibitor of aurora A kinase using novel in vivo pharmacodynamic assays". Clinical Cancer Research: An Official Journal of the American Association for Cancer Research. 17 (24): 7614–7624. doi:10.1158/1078-0432.CCR-11-1536. ISSN 1557-3265. PMID 22016509.

[3] Niu, Huifeng; Manfredi, Mark; Ecsedy, Jeffrey A. (2015-08-24). "Scientific Rationale Supporting the Clinical Development Strategy for the Investigational Aurora A Kinase Inhibitor Alisertib in Cancer". Frontiers in Oncology. 5: 189. doi:10.3389/fonc.2015.00189. ISSN 2234-943X. PMC 4547019. PMID 26380220.

[4] "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.

[5] "Research and Development Pipeline (As of February 5, 2014)" (PDF). Takeda Pharmaceutical Company Limited. February 5, 2014. p. 2. Retrieved 20 March 2014.

[6] "Takeda Announces Termination of Alisertib Phase 3 Trial in Relapsed or Refractory Peripheral T-cell Lymphoma".

[7] Taylor, Nick Paul (September 21, 2022). "Puma pounces on failed Takeda drug, snapping up cancer prospect for knockdown price".{{cite news}}: CS1 maint: url-status (link)

[8] Taylor, Phil (September 21, 2022). "Takeda farms out cancer drug alisertib to Puma Biotech".{{cite news}}: CS1 maint: url-status (link)

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]