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Details

Stereochemistry ACHIRAL
Molecular Formula C27H19ClFN4O4.Na.H2O
Molecular Weight 558.921
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALISERTIB SODIUM

SMILES

O.[Na+].COC1=CC(NC2=NC=C3CN=C(C4=CC(Cl)=CC=C4C3=N2)C5=C(OC)C=CC=C5F)=CC=C1C([O-])=O

InChI

InChIKey=WLPXWQKMVACWII-UHFFFAOYSA-M
InChI=1S/C27H20ClFN4O4.Na.H2O/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);;1H2/q;+1;/p-1

HIDE SMILES / InChI
Molecular Formula C27H20ClFN4O4
Molecular Weight 518.924
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula Na
Molecular Weight 22.98976928
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula HO
Molecular Weight 17.0073
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.takeda.com/news/2012/20120306_3946.html 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

CNS Penetrant
2588
Curator's Comment: Alisertib (MLN8237) achieved blood-brain barrier penetration

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 1.2 nM [IC50]
CAL-62
3
Target ID: CHEMBL1075413
Inhibitor
8504
 76.7 nM [IC50]
Inhibitor
8504
 16.0 nM [IC50]
Inhibitor
8504
 54.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3325 nM
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/34435684/
80 mg/m² 1 times / day multiple, oral
dose: 80 mg/m²
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ALISERTIB plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: UNKNOWN
1253 ng/mL
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/30985952
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ALISERTIB plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
15760 nM × h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/34435684/
80 mg/m² 1 times / day multiple, oral
dose: 80 mg/m²
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ALISERTIB plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: UNKNOWN
23386 ng × h/mL
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/30985952
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ALISERTIB plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
22.5 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/34435684/
80 mg/m² 1 times / day multiple, oral
dose: 80 mg/m²
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ALISERTIB plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: UNKNOWN
22.8 h
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/30985952
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ALISERTIB plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
1%
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/30985952
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ALISERTIB plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Sourcing

Sourcing

Vendor/AggregatorIDURL
001 Chemical
DY114921
https://www.001chemical.com/chem/search?q=DY114921
1PlusChem LLC
1P0038TQ
https://www.1pchem.com/search?query=1P0038TQ
A2B Chem
AB50606
http://a2bchem.com/prod/AB50606
AChemBlock
L21796
http://www.achemblock.com/catalogsearch/result/?q=L21796
AK Scientific
SYN5702
https://aksci.com/item_detail.php?cat=SYN5702
AK Scientific
X7389
https://aksci.com/item_detail.php?cat=X7389
Ambeed
A102516
http://www.ambeed.com/search/Search.html?keyword=A102516
Angene
AGN-PC-0ORXAX
http://www.angenechemical.com/productshow/AGN-PC-0ORXAX.html
AOBIOUS INC
AOB87191
http://aobious.com/aobious/search?search_query=AOB87191
ApexBio Technology
A4110
https://www.apexbt.com/catalogsearch/result/?q=A4110
AstaTech
42162
http://astatechinc.com/CPSResult.php?CRNO=42162
Axon MedChem
2003
https://www.axonmedchem.com/product/2003
BLD Pharm
BD239256
http://www.bldpharm.com/search/Search.html?keyword=BD239256
BOC Sciences
1028486-01-2
http://www.bocsci.com/description.asp?cas=1028486-01-2
Capot Chemical
22398
https://www.capotchem.com/search.do?q=22398
Cayman Chemical
13602
http://www.caymanchem.com/app/template/Product.vm/catalog/13602
ChemShuttle
124898
https://www.chemshuttle.com/catalogsearch/result/?q=124898
eMolecules
31231103
https://orderbb.emolecules.com/search/#?query=31231103
eNovation Chemicals
D210779
https://www.enovationchem.com/Products.asp?SEARCHTEXT=D210779&searchbtn.x=0&searchbtn.y=0
Excenen
EX-A024
http://www.excenen.com/searchresultlist.php?id=EX-A024
Hairui
HR144167
http://www.hairuichem.com/en/product/search.do?q=HR144167
KeyOrganics
AS-17005
http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-17005
Matrix Scientific
97249
http://www.matrixscientific.com/097249.html
mcule
MCULE-7766123608
https://mcule.com/MCULE-7766123608/
MedChem Express
HY-10971
https://www.medchemexpress.com/search.html?q=HY-10971&ft=&fa=&fp=
Molcore
MC114921
http://www.molcore.com/CatMC114921.html
Molnova
M10137
https://www.molnova.com/en/serch-list.html?keywords=M10137
MolPort
MolPort-009-679-457
https://www.molport.com/shop/molecule-link/MolPort-009-679-457
MuseChem
I000178
https://www.musechem.com/product/I000178.html
Ryan Scientific
101-93994
https://ryansci.com/products?q=101-93994&list_q=&search_type=exact
Ryan Scientific
AT_7519__HCl_salt
https://ryansci.com/products?q=AT_7519__HCl_salt&list_q=&search_type=exact
ShangHai Biochempartner
BCP000126
http://www.biochempartner.com/search_BCP000126
ShangHai Biochempartner
BCP01823
http://www.biochempartner.com/search_BCP01823
Synovel
SN-0360
http://www.synovellab.com/?s=SN-0360&submit=Search
Synovel
SN-0390
http://www.synovellab.com/?s=SN-0390&submit=Search
TargetMol
T2241
https://www.targetmol.com/search?keyword=T2241
Toronto Research Chemicals
C982915
https://www.trc-canada.com/product-detail/?CatNum=C982915
Toronto Research Chemicals
M425115
https://www.trc-canada.com/product-detail/?CatNum=M425115
PubMed

PubMed

TitleDatePubMed
A Cre-conditional MYCN-driven neuroblastoma mouse model as an improved tool for preclinical studies.
2015-06
Development of treatment strategies for advanced neuroblastoma.
2012-06
Aurora inhibitor MLN8237 in combination with docetaxel enhances apoptosis and anti-tumor activity in mantle cell lymphoma.
2011-04-01
A novel Aurora-A kinase inhibitor MLN8237 induces cytotoxicity and cell-cycle arrest in multiple myeloma.
2010-06-24
Drug-resistant aurora A mutants for cellular target validation of the small molecule kinase inhibitors MLN8054 and MLN8237.
2010-06-18
Discovery and development of aurora kinase inhibitors as anticancer agents.
2009-05-14
Patents

Patents

08026246
3
08653064
3
20080167292
3

Sample Use Guides

In Vivo Use Guide
50 mg twice daily for 7 days repeated every 21 days,administered on an empty stomach with the patient remaining nothing by mouth (NPO), except for water and prescribed medications, for 2 hours before and 1 hour after each dose, oral dose of Alisertib (MLN8237) should be taken with 8 ounces (1 cup, 240 mL) of water.
Route of Administration: Oral
In Vitro Use Guide
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 Mon Mar 31 20:57:24 GMT 2025
Edited
by admin
on Mon Mar 31 20:57:24 GMT 2025
Record UNII
T76P158V9D
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALISERTIB SODIUM
USAN   WHO-DD  
USAN  
Official Name English
MLN-8237-004
Preferred Name English
MLN8237-004
Code English
Alisertib sodium [WHO-DD]
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-, SODIUM SALT, HYDRATE (1:1:1)
Common Name English
ALISERTIB SODIUM [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C471
Created by admin on Mon Mar 31 20:57:24 GMT 2025 , Edited by admin on Mon Mar 31 20:57:24 GMT 2025
Code System Code Type Description
EVMPD
SUB128442
Created by admin on Mon Mar 31 20:57:24 GMT 2025 , Edited by admin on Mon Mar 31 20:57:24 GMT 2025
PRIMARY
CAS
1208255-63-3
Created by admin on Mon Mar 31 20:57:24 GMT 2025 , Edited by admin on Mon Mar 31 20:57:24 GMT 2025
PRIMARY
NCI_THESAURUS
C142912
Created by admin on Mon Mar 31 20:57:24 GMT 2025 , Edited by admin on Mon Mar 31 20:57:24 GMT 2025
PRIMARY
DRUG BANK
DBSALT002940
Created by admin on Mon Mar 31 20:57:24 GMT 2025 , Edited by admin on Mon Mar 31 20:57:24 GMT 2025
PRIMARY
FDA UNII
T76P158V9D
Created by admin on Mon Mar 31 20:57:24 GMT 2025 , Edited by admin on Mon Mar 31 20:57:24 GMT 2025
PRIMARY
SMS_ID
300000024071
Created by admin on Mon Mar 31 20:57:24 GMT 2025 , Edited by admin on Mon Mar 31 20:57:24 GMT 2025
PRIMARY
USAN
XX-124
Created by admin on Mon Mar 31 20:57:24 GMT 2025 , Edited by admin on Mon Mar 31 20:57:24 GMT 2025
PRIMARY
ChEMBL
CHEMBL483158
Created by admin on Mon Mar 31 20:57:24 GMT 2025 , Edited by admin on Mon Mar 31 20:57:24 GMT 2025
PRIMARY
PUBCHEM
56843791
Created by admin on Mon Mar 31 20:57:24 GMT 2025 , Edited by admin on Mon Mar 31 20:57:24 GMT 2025
PRIMARY
Related Record Type Details
Structure of ALISERTIB SODIUM ANHYDROUS
ANHYDROUS->SOLVATE
Structure of ALISERTIB
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of ALISERTIB
ACTIVE MOIETY
NIH
NCATS
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