MLN8054 SODIUM

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C25H14ClF2N4O2.Na
Molecular Weight	498.844
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].[O-]C(=O)C1=CC=C(NC2=NC=C3CN=C(C4=CC(Cl)=CC=C4C3=N2)C5=C(F)C=CC=C5F)C=C1

InChI

InChIKey=CPUPAOAXNTYRQJ-UHFFFAOYSA-M

InChI=1S/C25H15ClF2N4O2.Na/c26-15-6-9-17-18(10-15)23(21-19(27)2-1-3-20(21)28)29-11-14-12-30-25(32-22(14)17)31-16-7-4-13(5-8-16)24(33)34;/h1-10,12H,11H2,(H,33,34)(H,30,31,32);/q;+1/p-1

HIDE SMILES / InChI

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	C25H14ClF2N4O2
Molecular Weight	475.854
Charge	-1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17360485
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/20607239

MLN8054 is a reversible, ATP competitive inhibitor of recombinant Aurora A, developed by Millennium Pharmaceuticals. MLN8054 was tested in phase I clinical trials against advanced solid tumors. Reversible somnolence probably due to off-target inhibition of alpha-1 subunit of GABA-A receptor was dose limiting and prevented achievement of plasma concentrations predicted necessary for target modulation.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serine/threonine-protein kinase Aurora-A 37 Target ID: CHEMBL4722 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17360485	Inhibitor 8504		4.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Breast cancer 432 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20607239	Primary	Phase I 438	Unknown Approved Use Unknown
Colon cancer 66 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20607239	Primary	Phase I 438	Unknown Approved Use Unknown
Pancreatic cancer 98 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20607239	Primary	Phase I 438	Unknown Approved Use Unknown
Bladder cancer 16 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20607239	Primary	Phase I 438	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
2642 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20607239	15 mg 4 times / day multiple, oral dose: 15 mg route of administration: Oral experiment type: MULTIPLE co-administered: METHYLPHENIDATE	METHYLPHENIDATE	MLN8054 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2129 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20607239	20 mg 4 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered:		MLN8054 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
13203 nM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20607239	15 mg 4 times / day multiple, oral dose: 15 mg route of administration: Oral experiment type: MULTIPLE co-administered: METHYLPHENIDATE	METHYLPHENIDATE	MLN8054 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
10109 nM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20607239	20 mg 4 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered:		MLN8054 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P004LPZ	https://www.1pchem.com/search?query=1P004LPZ
AK Scientific	2558AH	https://aksci.com/item_detail.php?cat=2558AH
ApexBio Technology	A4114	https://www.apexbt.com/catalogsearch/result/?q=A4114
BLD Pharm	BD163533	http://www.bldpharm.com/search/Search.html?keyword=BD163533
Chem Scene	CS-0010	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0010
ChemShuttle	141348	https://www.chemshuttle.com/catalogsearch/result/?q=141348
eMolecules	31231105	https://orderbb.emolecules.com/search/#?query=31231105
eNovation Chemicals	D491488	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D491488&searchbtn.x=0&searchbtn.y=0
eNovation Chemicals	K09720	https://www.enovationchem.com/Products.asp?SEARCHTEXT=K09720&searchbtn.x=0&searchbtn.y=0
Exclusive Chemistry	2342	http://www.exchemistry.com/chem-catalog/product-2342.html
KeyOrganics	AS-74414	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-74414
mcule	MCULE-8254255695	https://mcule.com/MCULE-8254255695/
MedChem Express	HY-10180	https://www.medchemexpress.com/search.html?q=HY-10180&ft=&fa=&fp=
Molnova	M16315	https://www.molnova.com/en/serch-list.html?keywords=M16315
MolPort	MolPort-016-633-177	https://www.molport.com/shop/molecule-link/MolPort-016-633-177
MuseChem	M143159	https://www.musechem.com/product/M143159.html
MuseChem	R051392	https://www.musechem.com/product/R051392.html
ShangHai Biochempartner	BCP02261	http://www.biochempartner.com/search_BCP02261
TargetMol	T6315	https://www.targetmol.com/search?keyword=T6315
Toronto Research Chemicals	M425125	https://www.trc-canada.com/product-detail/?CatNum=M425125

PubMed

Title	Date	PubMed
Comprehensive analysis of kinase inhibitor selectivity.	2011-10-30	22037378
Phthalazinone pyrazoles as potent, selective, and orally bioavailable inhibitors of Aurora-A kinase.	2011-01-13	21128645
Activation state-dependent binding of small molecule kinase inhibitors: structural insights from biochemistry.	2010-11-24	21095574
A class of 2,4-bisanilinopyrimidine Aurora A inhibitors with unusually high selectivity against Aurora B.	2009-05-28	19402633
Antitumor activity of MLN8054, an orally active small-molecule inhibitor of Aurora A kinase.	2007-03-06	17360485

Patents

Sample Use Guides

In Vivo Use Guide

In clinical trials against advanced solid tumors MLN8054 was administered orally in multiple divided daily doses for 7 days to 21 consecutive days. A 14-day recovery period followed each dosing period, regardless of its duration. MLN8054 was supplied in capsules of 5 mg or 25 mg. MLN8054 will be given on an empty stomach. Patients were instructed to take nothing by mouth except for water and prescribed medications for 2 hours before and 1 hour after each dose.

Route of Administration: Oral

In Vitro Use Guide

Recombinant murine Aurora A protein was expressed in Sf9 cells and purified with GST affinity chromatography. The peptide substrate for Aurora A was conjugated with biotin (Biotin-GLRRASLG). Aurora A kinase (5 nM) was assayed in 50 mM Hepes (pH 7.5)/10 mM MgCl2/5 mM DTT/0.05% Tween 20/2 μM peptide substrate/3.3 μCi/ml [γ-33P]ATP at 2 μM by using Image FlashPlates (Perkin–Elmer).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:13:31 GMT 2025` Edited by `admin` on `Mon Mar 31 18:13:31 GMT 2025`
Record UNII	931G05H22J
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MLN8054 SODIUM

Common Name

English

BENZOIC ACID, 4-((9-CHLORO-7-(2,6-DIFLUOROPHENYL)-5H-PYRIMIDO(5,4-D)(2)BENZAZEPIN-2-YL)AMINO)-, MONOSODIUM SALT

Preferred Name

English

BENZOIC ACID, 4-((9-CHLORO-7-(2,6-DIFLUOROPHENYL)-5H-PYRIMIDO(5,4-D)(2)BENZAZEPIN-2-YL)AMINO)-, SODIUM SALT (1:1)

Common Name

English

Code System Code Type Description

CAS

869366-15-4