NAV

Entinostat

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

Identification

Generic Name
Entinostat
DrugBank Accession Number
DB11841
Background

Entinostat is under investigation for the treatment and other of Volunteers, Breast Cancer, Human Volunteers, and Normal Volunteers. Entinostat has been investigated for the treatment of Non-Small Lung Cancer, Epigenetic Therapy.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 376.416
Monoisotopic: 376.15354052
Chemical Formula
C21H20N4O3
Synonyms
  • Entinostat
  • Entinostatum
  • N-(2-aminophenyl)-4-(N-(pyridin-3-ylmethoxycarbonyl)aminomethyl)benzamide
  • N-[[4-[(2-aminoanilino)-oxomethyl]phenyl]methyl]carbamic acid 3-pyridinylmethyl ester
External IDs
  • BAY 86-5274
  • BAY86-5274
  • MS 27-275
  • MS 275
  • MS-27-275
  • MS-275
  • MS-275-27
  • SNDX 275
  • SNDX-275
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
AHistone deacetylase
inhibitor
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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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.
DrugInteraction
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AcrivastineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Entinostat.
AdenosineThe risk or severity of QTc prolongation can be increased when Adenosine is combined with Entinostat.
AjmalineThe risk or severity of QTc prolongation can be increased when Ajmaline is combined with Entinostat.
AlfuzosinThe risk or severity of QTc prolongation can be increased when Alfuzosin is combined with Entinostat.
AlimemazineThe risk or severity of QTc prolongation can be increased when Alimemazine is combined with Entinostat.
Food Interactions
Not Available

Categories

ATC Codes
L01XH05 — Entinostat
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Anilides
Direct Parent
Benzanilides
Alternative Parents
Benzamides / Benzoyl derivatives / Aniline and substituted anilines / Pyridines and derivatives / Heteroaromatic compounds / Carbamate esters / Secondary carboxylic acid amides / Organic carbonic acids and derivatives / Azacyclic compounds / Primary amines
show 4 more
Substituents
Amine / Amino acid or derivatives / Aniline or substituted anilines / Aromatic heteromonocyclic compound / Azacycle / Benzamide / Benzanilide / Benzoic acid or derivatives / Benzoyl / Carbamic acid ester
show 16 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
1ZNY4FKK9H
CAS number
209783-80-2
InChI Key
INVTYAOGFAGBOE-UHFFFAOYSA-N
InChI
InChI=1S/C21H20N4O3/c22-18-5-1-2-6-19(18)25-20(26)17-9-7-15(8-10-17)13-24-21(27)28-14-16-4-3-11-23-12-16/h1-12H,13-14,22H2,(H,24,27)(H,25,26)
IUPAC Name
(pyridin-3-yl)methyl N-({4-[(2-aminophenyl)carbamoyl]phenyl}methyl)carbamate
SMILES
NC1=CC=CC=C1NC(=O)C1=CC=C(CNC(=O)OCC2=CN=CC=C2)C=C1

References

General References
Not Available
PubChem Compound
4261
PubChem Substance
347828185
ChemSpider
4111
BindingDB
19410
ChEBI
132082
ChEMBL
CHEMBL27759
ZINC
ZINC000001488870
Wikipedia
Entinostat

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
3Active Not RecruitingTreatmentAdvanced Breast Cancer1
3Active Not RecruitingTreatmentAnatomic Stage III Breast Cancer AJCC v8 / Anatomic Stage IV Breast Cancer AJCC v8 / Breast Adenocarcinoma / HER2 negative / Locally Advanced Breast Carcinoma / Metastatic Breast Carcinoma / Recurrent Breast Carcinoma1
2Active Not RecruitingTreatmentAcute Myeloid Leukemia1
2Active Not RecruitingTreatmentBladder Cancer1
2Active Not RecruitingTreatmentDrug Relapse / Lymphoma / Refractory1

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 Solubility0.00574 mg/mLALOGPS
logP2.07ALOGPS
logP2.31Chemaxon
logS-4.8ALOGPS
pKa (Strongest Acidic)13.54Chemaxon
pKa (Strongest Basic)4.74Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area106.34 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity108.29 m3·mol-1Chemaxon
Polarizability39.39 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/MSsplash10-014l-4390000000-e6715b98ec8b20595909
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-427eb08ad8ffb2184cba
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00ou-6298000000-66983a6b5dac1b70e305
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-052f-9431000000-78c5304913456cab09e8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kf-9701000000-f76bb54f1a966bf0a65d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001l-5940000000-464792ffeec6973f321e
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-217.8065677
predicted
DarkChem Lite v0.1.0
[M-H]-185.7996
predicted
DeepCCS 1.0 (2019)
[M+H]+218.9348677
predicted
DarkChem Lite v0.1.0
[M+H]+188.15758
predicted
DeepCCS 1.0 (2019)
[M+Na]+218.0513677
predicted
DarkChem Lite v0.1.0
[M+Na]+195.17809
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Histone deacetylase (Protein Group)
Kind
Protein group
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
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...
Components:
NameUniProt ID
Histone deacetylase 1Q13547
Histone deacetylase 10Q969S8
Histone deacetylase 11Q96DB2
Histone deacetylase 2Q92769
Histone deacetylase 3O15379
Histone deacetylase 4P56524
Histone deacetylase 5Q9UQL6
Histone deacetylase 6Q9UBN7
Histone deacetylase 7Q8WUI4
Histone deacetylase 8Q9BY41
Histone deacetylase 9Q9UKV0
References
  1. Dunoyer-Geindre S, Kruithof EK: Epigenetic control of tissue-type plasminogen activator synthesis in human endothelial cells. Cardiovasc Res. 2011 Jun 1;90(3):457-63. doi: 10.1093/cvr/cvr028. Epub 2011 Jan 31. [Article]
  2. Kouraklis G, Theocharis S: Histone deacetylase inhibitors: a novel target of anticancer therapy (review). Oncol Rep. 2006 Feb;15(2):489-94. [Article]
  3. Rossig L, Li H, Fisslthaler B, Urbich C, Fleming I, Forstermann U, Zeiher AM, Dimmeler S: Inhibitors of histone deacetylation downregulate the expression of endothelial nitric oxide synthase and compromise endothelial cell function in vasorelaxation and angiogenesis. Circ Res. 2002 Nov 1;91(9):837-44. doi: 10.1161/01.res.0000037983.07158.b1. [Article]
  4. Kouraklis G, Theocharis S: Histone deacetylase inhibitors and anticancer therapy. Curr Med Chem Anticancer Agents. 2002 Jul;2(4):477-84. doi: 10.2174/1568011023353921. [Article]
  5. Wang Y, Curry HM, Zwilling BS, Lafuse WP: Mycobacteria inhibition of IFN-gamma induced HLA-DR gene expression by up-regulating histone deacetylation at the promoter region in human THP-1 monocytic cells. J Immunol. 2005 May 1;174(9):5687-94. doi: 10.4049/jimmunol.174.9.5687. [Article]
  6. Huang PH, Plass C, Chen CS: Effects of Histone Deacetylase Inhibitors on Modulating H3K4 Methylation Marks - A Novel Cross-Talk Mechanism between Histone-Modifying Enzymes. Mol Cell Pharmacol. 2011;3(2):39-43. [Article]

Drug created at October 20, 2016 20:53 / Updated at May 04, 2022 21:16