Abexinostat

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Abexinostat
Accession Number
DB12565  (DB05921)
Type
Small Molecule
Groups
Investigational
Description

Abexinostat has been used in trials studying the treatment of Sarcoma, Lymphoma, Leukemia, Lymphocytic, and Hodgkin Disease, among others. It is a novel, broad-spectrum hydroxamic acid-based inhibitor of histone deacetylase (HDAC) with potential antineoplastic activity.

Structure
Thumb
Synonyms
  • ABEXINOSTAT
External IDs
CRA 024781 / CRA 24781 / CRA-024781 / PCI 24781 / PCI-24781 / PZP-115891 / PZP115891
Categories
UNII
IYO470654U
CAS number
783355-60-2
Weight
Average: 397.431
Monoisotopic: 397.163770853
Chemical Formula
C21H23N3O5
InChI Key
MAUCONCHVWBMHK-UHFFFAOYSA-N
InChI
InChI=1S/C21H23N3O5/c1-24(2)13-17-16-5-3-4-6-18(16)29-19(17)21(26)22-11-12-28-15-9-7-14(8-10-15)20(25)23-27/h3-10,27H,11-13H2,1-2H3,(H,22,26)(H,23,25)
IUPAC Name
3-[(dimethylamino)methyl]-N-{2-[4-(hydroxycarbamoyl)phenoxy]ethyl}-1-benzofuran-2-carboxamide
SMILES
CN(C)CC1=C(OC2=CC=CC=C12)C(=O)NCCOC1=CC=C(C=C1)C(=O)NO

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action

Abexinostat is a novel histone deacetylase (HDAC) inhibitor. HDAC inhibitors target HDAC enzymes and inhibit the proliferation of cancer cells and induce cancer cell death, or apoptosis. Histone deacetylation is carried out by a family of related HDAC enzymes. Inhibition of these enzymes causes changes to chromatin structure and to gene expression patterns, which results in the inhibition of proliferation of cancer cells, and induction of apoptosis [1].

TargetActionsOrganism
UHistone deacetylase 1Not 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
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
VemurafenibThe risk or severity of QTc prolongation can be increased when Vemurafenib is combined with Abexinostat.Approved
Food Interactions
Not Available

References

General References
  1. Buggy JJ, Cao ZA, Bass KE, Verner E, Balasubramanian S, Liu L, Schultz BE, Young PR, Dalrymple SA: CRA-024781: a novel synthetic inhibitor of histone deacetylase enzymes with antitumor activity in vitro and in vivo. Mol Cancer Ther. 2006 May;5(5):1309-17. [PubMed:16731764]
External Links
PubChem Compound
11749858
PubChem Substance
347828788
ChemSpider
9924562
BindingDB
24622
ChEBI
92223
ChEMBL
CHEMBL2103863

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingTreatmentMetastatic Solid Tumors1
1CompletedTreatmentHodgkins Disease (HD) / Leukemia, Lymphocytic, Chronic / Multiple Myeloma (MM) / Neoplasms by Site / Non-Hodgkin's Lymphoma (NHL)1
1CompletedTreatmentHodgkins Disease (HD) / Leukemias / Lymphocytic / Malignant Lymphomas / Multiple Myeloma (MM) / Non-Hodgkin's Lymphoma (NHL)1
1, 2CompletedTreatmentHodgkins Disease (HD) / Malignant Lymphomas / Non-Hodgkin's Lymphoma (NHL)1
1, 2CompletedTreatmentSarcomas1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0767 mg/mLALOGPS
logP1.8ALOGPS
logP1.43ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)9.83ChemAxon
pKa (Strongest Basic)8.23ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.04 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity108.69 m3·mol-1ChemAxon
Polarizability42.77 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
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 benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzofurans
Sub Class
Not Available
Direct Parent
Benzofurans
Alternative Parents
Benzoic acids and derivatives / Phenoxy compounds / Phenol ethers / 2-heteroaryl carboxamides / Furoic acid and derivatives / Benzoyl derivatives / Alkyl aryl ethers / Aralkylamines / Heteroaromatic compounds / Trialkylamines
show 7 more
Substituents
Benzofuran / Benzoic acid or derivatives / 2-heteroaryl carboxamide / Benzoyl / Phenol ether / Phenoxy compound / Furoic acid or derivatives / Alkyl aryl ether / Aralkylamine / Monocyclic benzene moiety
show 21 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transcription regulatory region sequence-specific dna binding
Specific Function
Responsible for the deacetylation of lysine residues on the N-terminal part of the core histones (H2A, H2B, H3 and H4). Histone deacetylation gives a tag for epigenetic repression and plays an impo...
Gene Name
HDAC1
Uniprot ID
Q13547
Uniprot Name
Histone deacetylase 1
Molecular Weight
55102.615 Da

Drug created on October 20, 2016 16:55 / Updated on December 01, 2017 16:31