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Details

Stereochemistry ACHIRAL
Molecular Formula C27H20ClFN4O4
Molecular Weight 518.9245
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALISERTIB

SMILES

COc1cccc(c1C2=NCc3cnc(Nc4ccc(c(c4)OC)C(=O)O)nc3-c5ccc(cc52)Cl)F

InChI

InChIKey=ZLHFILGSQDJULK-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C27H20ClFN4O4
Molecular Weight 518.9245
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: http://adisinsight.springer.com/drugs/800025209

Alisertib (MLN8237) is an orally available selective aurora A kinase inhibitor developed by Takeda. Alisertib inhibited AAK over ABK with a selectivity of more than 200-fold in cells and produced a dose-dependent decrease in bipolar and aligned chromosomes in the HCT-116 xenograft model, a phenotype consistent with AAK inhibition. Alisertib inhibited proliferation of human tumor cell lines in vitro and produced tumor growth inhibition in solid tumor xenograft models and regressions in in vivo lymphoma models. It is currently in phase II clinical trials for acute myeloid leukaemia; B cell lymphoma; brain cancer; mesothelioma; prostate cancer; small cell lung cancer.

CNS Activity

Curator's Comment:: Alisertib (MLN8237) achieved blood-brain barrier penetration

Approval Year

TargetsConditions
PubMed

PubMed

TitleDatePubMed
A Cre-conditional MYCN-driven neuroblastoma mouse model as an improved tool for preclinical studies.
2015 Jun
Patents

Sample Use Guides

50 mg twice daily for 7 days repeated every 21 days,
Route of Administration: Oral
Alisertib (MLN8237) (0.5 uM) treatment inhibits the phosphorylation of Aurora A in human MM1.S and OPM1 cells, without affecting the Aurora B mediated histone H3 phosphorylation. Alisertib (MLN8237) (0.5 uM) induces 2- to 6-fold increase in G2/M phase in primary MM cells and cell lines, as well as significant apoptosis and senescence, involving the up-regulation of p53, p21 and p27, as well as PARP, caspase 3, and caspase 9 cleavage.
Substance Class Chemical
Created
by admin
on Fri Jun 25 22:44:22 UTC 2021
Edited
by admin
on Fri Jun 25 22:44:22 UTC 2021
Record UNII
T66ES73M18
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALISERTIB
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
MLN8237
Code English
ALISERTIB [WHO-DD]
Common Name English
ALISERTIB [USAN]
Common Name English
ALISERTIB [INN]
Common Name English
BENZOIC ACID, 4-((9-CHLORO-7-(2-FLUORO-6-METHOXYPHENYL)-5H-PYRIMIDO(5,4-D)(2)BENZAZEPIN-2-YL)AMINO)-2-METHOXY-
Common Name English
MLN-8237
Code English
4-((9-CHLORO-7-(2-FLUORO-6-METHOXYPHENYL)-5H-PYRIMIDO(5,4-D)(2)BENZAZEPIN-2-YL)AMINO)-2-METHOXY-BENZOIC ACID
Systematic Name English
MLN 8237
Code English
Classification Tree Code System Code
NCI_THESAURUS C129825
Created by admin on Fri Jun 25 22:44:22 UTC 2021 , Edited by admin on Fri Jun 25 22:44:22 UTC 2021
FDA ORPHAN DRUG 400313
Created by admin on Fri Jun 25 22:44:22 UTC 2021 , Edited by admin on Fri Jun 25 22:44:22 UTC 2021
NCI_THESAURUS C62556
Created by admin on Fri Jun 25 22:44:22 UTC 2021 , Edited by admin on Fri Jun 25 22:44:22 UTC 2021
EU-Orphan Drug EU/3/12/1074
Created by admin on Fri Jun 25 22:44:22 UTC 2021 , Edited by admin on Fri Jun 25 22:44:22 UTC 2021
FDA ORPHAN DRUG 369112
Created by admin on Fri Jun 25 22:44:22 UTC 2021 , Edited by admin on Fri Jun 25 22:44:22 UTC 2021
Code System Code Type Description
EVMPD
SUB128442
Created by admin on Fri Jun 25 22:44:22 UTC 2021 , Edited by admin on Fri Jun 25 22:44:22 UTC 2021
PRIMARY
FDA UNII
T66ES73M18
Created by admin on Fri Jun 25 22:44:22 UTC 2021 , Edited by admin on Fri Jun 25 22:44:22 UTC 2021
PRIMARY
NCI_THESAURUS
C71717
Created by admin on Fri Jun 25 22:44:22 UTC 2021 , Edited by admin on Fri Jun 25 22:44:22 UTC 2021
PRIMARY
EPA CompTox
1028486-01-2
Created by admin on Fri Jun 25 22:44:22 UTC 2021 , Edited by admin on Fri Jun 25 22:44:22 UTC 2021
PRIMARY
DRUG BANK
DB05220
Created by admin on Fri Jun 25 22:44:22 UTC 2021 , Edited by admin on Fri Jun 25 22:44:22 UTC 2021
PRIMARY
MESH
C550258
Created by admin on Fri Jun 25 22:44:22 UTC 2021 , Edited by admin on Fri Jun 25 22:44:22 UTC 2021
PRIMARY
ChEMBL
CHEMBL483158
Created by admin on Fri Jun 25 22:44:22 UTC 2021 , Edited by admin on Fri Jun 25 22:44:22 UTC 2021
PRIMARY
PUBCHEM
24771867
Created by admin on Fri Jun 25 22:44:22 UTC 2021 , Edited by admin on Fri Jun 25 22:44:22 UTC 2021
PRIMARY
INN
9331
Created by admin on Fri Jun 25 22:44:22 UTC 2021 , Edited by admin on Fri Jun 25 22:44:22 UTC 2021
PRIMARY
CAS
1028486-01-2
Created by admin on Fri Jun 25 22:44:22 UTC 2021 , Edited by admin on Fri Jun 25 22:44:22 UTC 2021
PRIMARY
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