Alisertib

Identification

Name
Alisertib
Accession Number
DB05220
Type
Small Molecule
Groups
Investigational
Description

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

Structure
Thumb
Synonyms
Not Available
External IDs
MLN 8237 / MLN-8237 / MLN8237
Categories
UNII
T66ES73M18
CAS number
Not Available
Weight
Average: 518.93
Monoisotopic: 518.115711
Chemical Formula
C27H20ClFN4O4
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(11),2,4,6,9,12,14-heptaen-4-yl]amino}-2-methoxybenzoic acid
SMILES
COC1=CC(NC2=NC=C3CN=C(C4=C(C=CC(Cl)=C4)C3=N2)C2=C(F)C=CC=C2OC)=CC=C1C(O)=O

Pharmacology

Indication

For the treatment of various forms of cancer.

Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAurora kinase ANot AvailableHuman
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
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
24771867
PubChem Substance
347827718
ChemSpider
24700147
BindingDB
50277545
ChEBI
125628
ChEMBL
CHEMBL483158
PharmGKB
PA166165015
HET
A5B
PDB Entries
5ia0

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingBasic ScienceAdvanced Solid Tumors / Relapsed/Refractory Lymphoma1
1Active Not RecruitingTreatmentAdenocarcinomas / Neoplasms, Pancreatic1
1Active Not RecruitingTreatmentAdult Anaplastic Astrocytoma / Adult Anaplastic Ependymoma / Adult Anaplastic Oligodendroglioma / Adult Brain Stem Glioma / Adult Diffuse Astrocytoma / Adult Giant Cell Glioblastoma / Adult Glioblastoma / Adult Gliosarcoma / Adult Mixed Glioma / Adult Oligodendroglioma / Adult Pilocytic Astrocytoma / Adult Pineal Gland Astrocytoma / Adult Subependymal Giant Cell Astrocytoma / Recurrent Adult Brain Tumor1
1Active Not RecruitingTreatmentAdult B Acute Lymphoblastic Leukemia / Adult T Acute Lymphoblastic Leukemia / Anaplastic Large Cell Lymphoma / Angioimmunoblastic T-Cell Lymphoma / Chronic Lymphocytic Leukaemia (CLL) / Cutaneous B-Cell Non-Hodgkin Lymphoma / Extranodal Marginal Zone Lymphoma of Mucosa-Associated Lymphoid Tissue / Hepatosplenic T-Cell Lymphoma / Intraocular Lymphoma / Lymphomatous Involvement of Non-Cutaneous Extranodal Site / Mature T-Cell and NK-Cell Non-Hodgkin Lymphoma / Nodal Marginal Zone Lymphoma / Primary Cutaneous B-Cell Non-Hodgkin Lymphoma / Recurrent Adult Acute Lymphoblastic Leukemia / Recurrent Adult Burkitt Lymphoma / Recurrent Adult Diffuse Large Cell Lymphoma / Recurrent Adult Diffuse Mixed Cell Lymphoma / Recurrent Adult Diffuse Small Cleaved Cell Lymphoma / Recurrent Adult Grade III Lymphomatoid Granulomatosis / Recurrent Adult Hodgkin's Lymphoma / Recurrent Adult Immunoblastic Lymphoma / Recurrent Adult Lymphoblastic Lymphoma / Recurrent Adult T-Cell Leukemia/Lymphoma / Recurrent Cutaneous T-Cell Non-Hodgkin Lymphoma / Recurrent Grade 1 Follicular Lymphoma / Recurrent Grade 2 Follicular Lymphoma / Recurrent Grade 3 Follicular Lymphoma / Recurrent Mantle Cell Lymphoma / Recurrent Marginal Zone Lymphoma / Recurrent Mycosis Fungoides and Sezary Syndrome / Recurrent Non-Hodgkin Lymphoma / Recurrent Primary Cutaneous T-Cell Non-Hodgkin Lymphoma / Recurrent Small Lymphocytic Lymphoma / Refractory Chronic Lymphocytic Leukemia / Refractory Hairy Cell Leukemia / Small Intestinal Lymphoma / Splenic Marginal Zone Lymphoma / T-Cell Large Granular Lymphocyte Leukemia / Testicular Lymphoma / Waldenstrom's Macroglobulinemia (WM)1
1Active Not RecruitingTreatmentAdvanced Solid Tumors / Malignant Lymphomas1
1Active Not RecruitingTreatmentEstrogen Receptor Positive / Progesterone Receptor Positive / Recurrent Breast Carcinoma / Stage IIIB Breast Cancer / Stage IIIC Breast Cancer / Stage IV Breast Cancer1
1Active Not RecruitingTreatmentHead and Neck Carcinoma1
1Active Not RecruitingTreatmentHigh Grade B-Cell Lymphoma With MYC and BCL2 or BCL6 Rearrangements / MYC Positive / Recurrent B-Cell Non-Hodgkin Lymphoma / Recurrent Burkitt Lymphoma / Recurrent Diffuse Large B-Cell Lymphoma / Recurrent Follicular Lymphoma / Recurrent Hodgkin Lymphoma / Recurrent Mantle Cell Lymphoma / Recurrent Mature T- and NK-Cell Non-Hodgkin Lymphoma / Refractory B-Cell Non-Hodgkin Lymphoma / Refractory Burkitt Lymphoma / Refractory Diffuse Large B-Cell Lymphoma / Refractory Follicular Lymphoma / Refractory Hodgkin Lymphoma / Refractory Mantle Cell Lymphoma / Refractory Mature T-Cell and NK-Cell Non-Hodgkin Lymphoma1
1Active Not RecruitingTreatmentMalignant Digestive System Neoplasm1
1Active Not RecruitingTreatmentMucinous Adenocarcinoma of the Colon / Mucinous Adenocarcinoma of the Rectum / Recurrent Colon Cancer / Recurrent Rectal Cancer / Signet Ring Adenocarcinoma of the Colon / Signet Ring Adenocarcinoma of the Rectum / Stage IIIA Colon Cancer / Unspecified Adult Solid Tumor, Protocol Specific1
1CompletedTreatmentAcute Myelogenous Leukaemia (AML)1
1CompletedTreatmentAdenocarcinoma of the Prostate / Advanced Solid Tumors1
1CompletedTreatmentAdvanced Malignancies2
1CompletedTreatmentAdvanced Solid Tumors1
1CompletedTreatmentAdvanced Solid Tumors / Cancer, Ovarian / Lung Cancer Small Cell Lung Cancer (SCLC)1
1CompletedTreatmentAdvanced Solid Tumors / Malignant Lymphomas2
1CompletedTreatmentAdvanced Solid Tumors / Relapsed/Refractory Lymphoma1
1CompletedTreatmentAnaplastic Large Cell Lymphoma / Angioimmunoblastic T-cell Lymphoma (AITL) / B-Cell Chronic Lymphocytic Leukemia (B-CLL) / B-cell Follicular Lymphoma / B-cell Mantle Cell Lymphoma / B-cell Marginal Zone Lymphoma / B-cell Small Lymphocytic Lymphoma (SLL) / Enteropathy Associated T-cell Lymphoma (EATCL) / Lymphoma, Large B-Cell, Diffuse (DLBCL) / Multiple Myeloma (MM) / NK Lymphoma (NKL) / Noncutaneous Peripheral T-cell Lymphoma Not Otherwise Specified (PTCL-NOS) / Waldenstrom's Macroglobulinemia (WM)1
1CompletedTreatmentCentral nervous system neoplasms malignant NEC / Genitourinary Neoplasms Malignancy and Gender Unspecified / Malignant Neoplasm of Breast / Malignant Neoplasm of Gastrointestinal Tract / Malignant Neoplasm of Thorax / Melanoma / Neoplasms, Head and Neck1
1CompletedTreatmentMalignant Lymphomas / Tumors, Solid1
1CompletedTreatmentNeuroblastomas / Unspecified Childhood Solid Tumor, Excluding CNS1
1Not Yet RecruitingTreatmentCD30-positive Lymphoma / CD30-positive Solid Tumor1
1RecruitingTreatmentAcinar Cell Adenocarcinoma of the Pancreas / Duct Cell Adenocarcinoma of the Pancreas / Recurrent Pancreatic Cancer / Stage III Pancreatic Cancer / Stage IV Pancreatic Cancer / Unspecified Adult Solid Tumor, Protocol Specific1
1RecruitingTreatmentAdvanced Nonhematologic Malignancies1
1RecruitingTreatmentMetastatic Breast Cancer (MBC) / Tumors, Solid1
1RecruitingTreatmentRecurrent B-Cell Non-Hodgkin Lymphoma / Recurrent Mantle Cell Lymphoma / Refractory B-Cell Non-Hodgkin Lymphoma / Refractory Mantle Cell Lymphoma1
1TerminatedTreatmentBurkitt's Lymphoma / Follicular Lymphoma (FL) / Lymphoma, Large B-Cell, Diffuse (DLBCL)1
1TerminatedTreatmentNeoplasms, Advanced or Metastatic1
1WithdrawnTreatmentMalignant Neoplasms of Digestive Organs / Malignant Neoplasms of Female Genital Organs / Malignant Neoplasms of Lip Oral Cavity and Pharynx / Malignant Neoplasms of Male Genital Organs1
1, 2Active Not RecruitingTreatmentAdenocarcinoma of the Prostate / Hormone-Resistant Prostate Cancer / Recurrent Prostate Cancer / Stage IV Prostate Cancer1
1, 2Active Not RecruitingTreatmentNeuroblastomas1
1, 2CompletedTreatmentAdvanced Nonhematological Malignancies / Gastroesophageal Adenocarcinoma / Head and Neck Squamous Cell Carcinoma (HNSCC) / Lung Cancer Non-Small Cell Cancer (NSCLC) / Lung Cancer Small Cell Lung Cancer (SCLC) / Metastatic Breast Cancer (MBC)1
1, 2CompletedTreatmentRefractory Multiple Myeloma1
1, 2SuspendedTreatmentMetastatic Non-Small Cell Lung Cancer / Non-Small Cell Lung Cancer Recurrent1
2Active Not RecruitingTreatmentCarcinoma, Breast / Fallopian Tube Cancer / Malignant Peritoneal Neoplasm / Ovarian Carcinoma1
2Active Not RecruitingTreatmentExtranodal Marginal Zone B-cell Lymphoma of Mucosa-associated Lymphoid Tissue / Nodal marginal zone B-cell lymphomas / Recurrent Adult Burkitt Lymphoma / Recurrent Adult Diffuse Large Cell Lymphoma / Recurrent Grade 1 Follicular Lymphoma / Recurrent Grade 2 Follicular Lymphoma / Recurrent Grade 3 Follicular Lymphoma / Recurrent Mantle Cell Lymphoma / Recurrent Marginal Zone Lymphoma / Splenic Marginal Zone Lymphoma / Waldenstrom's Macroglobulinemia (WM)1
2Active Not RecruitingTreatmentLeukemia Acute Myeloid Leukemia (AML)1
2Active Not RecruitingTreatmentLung Cancer Small Cell Lung Cancer (SCLC)1
2Active Not RecruitingTreatmentLung Cancers / Mesothelioma1
2CompletedTreatmentAcute Myelogenous Leukaemia (AML) / High-Grade Myelodysplastic Syndrome1
2CompletedTreatmentAdult Nasal Type Extranodal NK/T-Cell Lymphoma / Anaplastic Large Cell Lymphoma / Angioimmunoblastic T-Cell Lymphoma / Hepatosplenic T-Cell Lymphoma / Mature T-Cell and NK-Cell Non-Hodgkin Lymphoma / Recurrent Adult Non-Hodgkin Lymphoma / Recurrent Adult T-Cell Leukemia/Lymphoma1
2CompletedTreatmentBurkitt's Lymphoma / Lymphoma, Large B-Cell, Diffuse (DLBCL) / Mantle Cell Lymphoma (MCL) / Precursor B-lymphoblastic Leukemia/Lymphoma / T-cell Lymphoma, Excluding Primary Cutaneous T-cell Lymphoma / Transformed Follicular Lymphoma With ≥ 50% Diffuse Large Cell Component1
2CompletedTreatmentChildhood Hepatoblastoma / Hepatoblastomas / Previously Treated Childhood Rhabdomyosarcoma / Recurrent Childhood Acute Lymphoblastic Leukemia / Recurrent Childhood Acute Myeloid Leukemia / Recurrent Childhood Kidney Neoplasm / Recurrent Childhood Malignant Germ Cell Tumor / Recurrent Childhood Rhabdomyosarcoma / Recurrent Childhood Soft Tissue Sarcoma / Recurrent Ewing Sarcoma/Peripheral Primitive Neuroectodermal Tumor / Recurrent Neuroblastoma / Recurrent Osteosarcoma / Recurrent Wilms Tumor and Other Childhood Kidney Tumors1
2CompletedTreatmentMyxofibrosarcoma / Recurrent Adult Soft Tissue Sarcoma / Recurrent Leiomyosarcoma / Recurrent Liposarcoma / Recurrent Malignant Peripheral Nerve Sheath Tumor / Recurrent Undifferentiated Pleomorphic Sarcoma / Stage III Soft Tissue Sarcoma / Stage III Soft Tissue Sarcoma AJCC v7 / Stage IV Soft Tissue Sarcoma / Stage IV Soft Tissue Sarcoma AJCC v71
2CompletedTreatmentNeuroendocrine Prostate Cancer / Prostate Adenocarcinoma Plus > 50% Immunohistochemical Staining for Neuroendocrine Markers / Small Cell Prostate Cancer1
2CompletedTreatmentOvarian Carcinoma1
2CompletedTreatmentRecurrent Uterine Corpus Sarcoma / Uterine Corpus Leiomyosarcoma1
2Not Yet RecruitingTreatmentBladder Cancers / Transitional Cell Carcinoma1
2RecruitingTreatmentAtypical Teratoid Rhabdoid Tumors (ATRT) / Malignant Rhabdoid Tumors (MRT)1
2RecruitingTreatmentCancer, Breast / Carcinoma, Breast / Malignant Neoplasm of Breast / Tumors, Breast1
2RecruitingTreatmentEstrogen Receptor Negative / Estrogen Receptor Positive / Estrogen Receptor Status / HER2/Neu Negative / Invasive Breast Carcinoma / One to five years postmenopausal / Stage III Breast Cancer / Stage IIIA Breast Cancer / Stage IIIB Breast Cancer / Stage IIIC Breast Cancer / Stage IV Breast Cancer1
3Active Not RecruitingTreatmentPeripheral T-cell lymphoma unspecified refractory / Relapsed Peripheral T-Cell Lymphoma1
Not AvailableNo Longer AvailableNot AvailableProstate Cancer1
Not AvailableRecruitingTreatmentAcute Megakaryoblastic Leukemia / Agnogenic Myeloid Metaplasia / Primary Myelofibrosis1

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
Polarizability52.18 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

Taxonomy

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
Benzazepine / O-methoxybenzoic acid or derivatives / Benzoic acid or derivatives / Benzoic acid / Methoxyaniline / Phenoxy compound / Anisole / Benzoyl / Methoxybenzene / Aniline or substituted anilines
show 37 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
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

Drug created on October 21, 2007 16:24 / Updated on December 01, 2017 15:35