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
Structure for Entinostat (DB11841)
- 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
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism AHistone deacetylase inhibitorHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcrivastine The risk or severity of QTc prolongation can be increased when Acrivastine is combined with Entinostat. Adenosine The risk or severity of QTc prolongation can be increased when Adenosine is combined with Entinostat. Ajmaline The risk or severity of QTc prolongation can be increased when Ajmaline is combined with Entinostat. Alfuzosin The risk or severity of QTc prolongation can be increased when Alfuzosin is combined with Entinostat. Alimemazine The risk or severity of QTc prolongation can be increased when Alimemazine is combined with Entinostat. Amantadine The risk or severity of QTc prolongation can be increased when Amantadine is combined with Entinostat. Ambroxol The risk or severity of methemoglobinemia can be increased when Entinostat is combined with Ambroxol. Amifampridine The risk or severity of QTc prolongation can be increased when Amifampridine is combined with Entinostat. Amiodarone The risk or severity of QTc prolongation can be increased when Entinostat is combined with Amiodarone. Amisulpride The risk or severity of QTc prolongation can be increased when Entinostat is combined with Amisulpride. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - 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
- External Links
- PubChem Compound
- 4261
- PubChem Substance
- 347828185
- ChemSpider
- 4111
- BindingDB
- 19410
- ChEBI
- 132082
- ChEMBL
- CHEMBL27759
- ZINC
- ZINC000001488870
- Wikipedia
- Entinostat
Clinical Trials
- Clinical Trials
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
Property Value Source Water Solubility 0.00574 mg/mL ALOGPS logP 2.07 ALOGPS logP 2.31 Chemaxon logS -4.8 ALOGPS pKa (Strongest Acidic) 13.54 Chemaxon pKa (Strongest Basic) 4.74 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 106.34 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 108.29 m3·mol-1 Chemaxon Polarizability 39.39 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- 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:
References
- 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]
- Kouraklis G, Theocharis S: Histone deacetylase inhibitors: a novel target of anticancer therapy (review). Oncol Rep. 2006 Feb;15(2):489-94. [Article]
- 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]
- 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]
- 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]
- 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