NAV

Alisertib

Identification

Generic Name
Alisertib
DrugBank Accession Number
DB05220
Background

Alisertib is a novel aurora A kinase inhibitor under investigation for the treatment of various forms of cancer.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 518.93
Monoisotopic: 518.115711
Chemical Formula
C27H20ClFN4O4
Synonyms
  • Alisertib
External IDs
  • MLN 8237
  • MLN-8237
  • MLN8237

Pharmacology

Indication

For the treatment of various forms of cancer.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAurora kinase A
inhibitor
regulator
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Alisertib sodiumT76P158V9D1208255-63-3WLPXWQKMVACWII-UHFFFAOYSA-M

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzazepines. These are organic compounds containing a benzene ring fused to an azepine ring (unsaturated seven-membered heterocycle with one nitrogen atom replacing a carbon atom).
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzazepines
Sub Class
Not Available
Direct Parent
Benzazepines
Alternative Parents
O-methoxybenzoic acids and derivatives / Benzoic acids / Methoxyanilines / Benzoyl derivatives / Phenoxy compounds / Methoxybenzenes / Anisoles / Azepines / Fluorobenzenes / Alkyl aryl ethers
show 16 more
Substituents
Alkyl aryl ether / Amine / Amino acid / Amino acid or derivatives / Aminopyrimidine / Aniline or substituted anilines / Anisole / Aromatic heteropolycyclic compound / Aryl chloride / Aryl fluoride
show 37 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
T66ES73M18
CAS number
1028486-01-2
InChI Key
ZLHFILGSQDJULK-UHFFFAOYSA-N
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)
IUPAC Name
4-{[13-chloro-10-(2-fluoro-6-methoxyphenyl)-3,5,9-triazatricyclo[9.4.0.0^{2,7}]pentadeca-1(15),2,4,6,9,11,13-heptaen-4-yl]amino}-2-methoxybenzoic acid
SMILES
COC1=CC(NC2=NC=C3CN=C(C4=CC(Cl)=CC=C4C3=N2)C2=C(OC)C=CC=C2F)=CC=C1C(O)=O

References

General References
Not Available
PubChem Compound
24771867
PubChem Substance
347827718
ChemSpider
24700147
BindingDB
50277545
ChEBI
125628
ChEMBL
CHEMBL483158
ZINC
ZINC000040939534
PharmGKB
PA166165015
PDBe Ligand
A5B
Wikipedia
Alisertib
PDB Entries
5ia0

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentRefractory Peripheral T-Cell Lymphoma / Relapsed Peripheral T-Cell Lymphoma1
2Active Not RecruitingTreatmentAtypical teratoid/rhabdoid tumour of CNS / Malignant Rhabdoid Tumors (MRT)1
2Active Not RecruitingTreatmentBreast Cancer Stage IIIc / Breast Cancer, Stage III / Breast Cancer, Stage IIIB / Carcinoma Breast Stage IV / Estrogen Receptor Status / HER2/Neu Negative / Invasive Breast Carcinoma / Postmenopausal / Stage IIIA Breast Cancer1
2Active Not RecruitingTreatmentBreast Cancer / Breast Carcinoma / Breast Tumor / Malignant Breast Neoplasm1
2CompletedTreatmentAcute Myeloid Leukemia1
2CompletedTreatmentAcute Myeloid Leukemia / High-grade Myelodysplastic Syndromes (MDS)1
2CompletedTreatmentAdult Nasal Type Extranodal NK/T-Cell Lymphoma / Anaplastic Large Cell Lymphoma / Angioimmunoblastic T-cell Lymphoma (AITL) / Hepato-splenic T-cell Lymphoma / Mature T-Cell and NK-Cell Non-Hodgkin Lymphoma / Recurrent Adult Non-Hodgkin Lymphoma / Recurrent Adult T-Cell Leukemia/Lymphoma1
2CompletedTreatmentBladder Cancer / Transitional Cell Carcinoma1
2CompletedTreatmentBreast Carcinoma / Fallopian Tube Cancer / Ovarian Carcinoma / Peritoneal Cancer1
2CompletedTreatmentBurkitt Lymphoma / Diffuse Large B-Cell Lymphoma (DLBCL) / Mantle Cell Lymphoma (MCL) / T-cell Lymphoma, Excluding Primary Cutaneous T-cell Lymphoma / Transformed Follicular Lymphoma With ≥ 50% Diffuse Large Cell Component1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00149 mg/mLALOGPS
logP5ALOGPS
logP5.5Chemaxon
logS-5.5ALOGPS
pKa (Strongest Acidic)4.28Chemaxon
pKa (Strongest Basic)3.01Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area105.93 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity137.21 m3·mol-1Chemaxon
Polarizability52.31 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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Details1. Aurora kinase A
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Regulator
General Function
Protein serine/threonine/tyrosine kinase activity
Specific Function
Mitotic serine/threonine kinases that contributes to the regulation of cell cycle progression. Associates with the centrosome and the spindle microtubules during mitosis and plays a critical role i...
Gene Name
AURKA
Uniprot ID
O14965
Uniprot Name
Aurora kinase A
Molecular Weight
45809.03 Da
References
  1. de Groot CO, Hsia JE, Anzola JV, Motamedi A, Yoon M, Wong YL, Jenkins D, Lee HJ, Martinez MB, Davis RL, Gahman TC, Desai A, Shiau AK: A Cell Biologist's Field Guide to Aurora Kinase Inhibitors. Front Oncol. 2015 Dec 21;5:285. doi: 10.3389/fonc.2015.00285. eCollection 2015. [Article]

Drug created at October 21, 2007 22:24 / Updated at June 30, 2022 21:24