Citarinostat
PubChem CID
53340426
Structure
Molecular Formula
Synonyms
- Citarinostat
- 1316215-12-9
- ACY-241
- HDAC-IN-2
- 2-((2-Chlorophenyl)(phenyl)amino)-N-(7-(hydroxyamino)-7-oxoheptyl)pyrimidine-5-carboxamide
Molecular Weight
467.9 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
- Create:2011-08-31
- Modify:2025-01-04
Description
Citarinostat is under investigation in clinical trial NCT02886065 (A Study of PVX-410, a Cancer Vaccine, and Citarinostat +/- Lenalidomide for Smoldering MM).
Citarinostat is an orally available histone deacetylase (HDAC) inhibitor, with potential antineoplastic activity. Upon oral administration, citarinostat inhibits the activity of HDACs; this results in an accumulation of highly acetylated chromatin histones, the induction of chromatin remodeling and an altered pattern of gene expression. This leads to the inhibition of tumor oncogene transcription, and the selective transcription of tumor suppressor genes, which inhibit tumor cell division and induce tumor cell apoptosis. HDAC, an enzyme upregulated in many tumor types, deacetylates chromatin histone proteins.
CITARINOSTAT is a small molecule drug with a maximum clinical trial phase of II (across all indications) and has 4 investigational indications.
Chemical Structure Depiction
2-(N-(2-chlorophenyl)anilino)-N-[7-(hydroxyamino)-7-oxoheptyl]pyrimidine-5-carboxamide
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
InChI=1S/C24H26ClN5O3/c25-20-12-7-8-13-21(20)30(19-10-4-3-5-11-19)24-27-16-18(17-28-24)23(32)26-15-9-2-1-6-14-22(31)29-33/h3-5,7-8,10-13,16-17,33H,1-2,6,9,14-15H2,(H,26,32)(H,29,31)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
VLIUIBXPEDFJRF-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
C1=CC=C(C=C1)N(C2=CC=CC=C2Cl)C3=NC=C(C=N3)C(=O)NCCCCCCC(=O)NO
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C24H26ClN5O3
Computed by PubChem 2.2 (PubChem release 2021.10.14)
1316215-12-9
- 2-((2-Chlorophenyl)(phenyl)amino)-N-(7-(hydroxyamino)-7-oxoheptyl)pyrimidine-5-carboxamide
- ACY-241
- ACY241
- citarinostat
- Citarinostat
- 1316215-12-9
- ACY-241
- HDAC-IN-2
- 2-((2-Chlorophenyl)(phenyl)amino)-N-(7-(hydroxyamino)-7-oxoheptyl)pyrimidine-5-carboxamide
- Citarinostat [USAN]
- 2-(N-(2-chlorophenyl)anilino)-N-[7-(hydroxyamino)-7-oxoheptyl]pyrimidine-5-carboxamide
- ACY241
- Citarinostat(ACY-241)
- CITARINOSTAT [INN]
- 441P620G3P
- Citarinostat (ACY-241)
- CITARINOSTAT [WHO-DD]
- UNII-441P620G3P
- 5-Pyrimidinecarboxamide, 2-[(2-chlorophenyl)phenylamino]-N-[7-(hydroxyamino)-7-oxoheptyl]-
- Citarinostat (USAN)
- Compound (I) [WO2016200919]
- 2-((2-Chlorophenyl)phenylamino)-N-(7-(hydroxyamino)-7-oxoheptyl)-5-pyrimidinecarboxamide
- 5-Pyrimidinecarboxamide, 2-((2-chlorophenyl)phenylamino)-N-(7-(hydroxyamino)-7-oxoheptyl)-
- 7-({2-[(2-chlorophenyl)(phenyl)amino]pyrimidin-5-yl}formamido)-N-hydroxyheptanamide
- 2-[(2-Chlorophenyl)phenylamino]-N-[7-(hydroxyamino)-7-oxoheptyl]-5-pyrimidinecarboxamide
- Compound (I) (WO2016200919)
- citarinostatum
- 2-(N-(2-chlorophenyl)anilino)-N-(7-(hydroxyamino)-7-oxoheptyl)pyrimidine-5-carboxamide
- 2-[(2-chlorophenyl)(phenyl)amino]-N-[7-(hydroxyamino)-7-oxoheptyl]pyrimidine-5-carboxamide
- 2-[(2-Chlorophenyl)phenylamino]-N-[7-(hydroxyamino)-7-oxoheptyl]pyrimidine-5-carboxamide
- 7-((2-((2-chlorophenyl)(phenyl)amino)pyrimidin-5-yl)formamido)-N-hydroxyheptanamide
- 2-((2-CHLOROPHENYL)PHENYLAMINO)-N-(7-(HYDROXYAMINO)-7-OXOHEPTYL)PYRIMIDINE-5-CARBOXAMIDE
- MFCD28023593
- Citarinostat (USAN/INN)
- GTPL9426
- SCHEMBL2225863
- CHEMBL3693786
- EX-A379
- BDBM110036
- BCP09545
- s8464
- AKOS024464693
- CCG-269430
- CS-5140
- DB15449
- Histone Deacetylase Inhibitor ACY-241
- SB18732
- AC-33086
- AS-74355
- CC-96241
- HY-15994
- DB-239604
- D10918
- J-690128
- J-690129
- Q27258687
- (2-((2-chlorophenyl)(phenyl)amino)-N-(7-(hydroxyamino)-7-oxoheptyl)pyrimidine-5-carboxamide)
- {4-[4-({3-[(2-Methyl-1,3-benzothiazol-6-yl)amino]-3-oxopropyl}amino)-4-oxobutyl]benzyl}malonic acid
- US8609678, 2-((2-chlorophenyl)(phenyl)amino)-N-(7-(hydroxyamino)-7-oxoheptyl)pyrimidine-5-carboxamide [89]
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
467.9 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
4.1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
11
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
467.1724174 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
467.1724174 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
107Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
33
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
597
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Parent, Exact Count
Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
Histone Deacetylase Inhibitors
Compounds that inhibit HISTONE DEACETYLASES. This class of drugs may influence gene expression by increasing the level of acetylated HISTONES in specific CHROMATIN domains. (See all compounds classified as Histone Deacetylase Inhibitors.)
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=VLIUIBXPEDFJRF-UHFFFAOYSA-N
- ChEMBLLICENSEAccess to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).http://www.ebi.ac.uk/Information/termsofuse.htmlChEMBL Protein Target Treehttps://www.ebi.ac.uk/chembl/g/#browse/targets
- ChemIDplusCitarinostat [USAN]https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=1316215129ChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- DrugBankLICENSECreative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)https://www.drugbank.ca/legal/terms_of_useCitarinostathttps://www.drugbank.ca/drugs/DB15449
- FDA Global Substance Registration System (GSRS)LICENSEUnless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.https://www.fda.gov/about-fda/about-website/website-policies#linking
- ClinicalTrials.govLICENSEThe ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
- Drug Gene Interaction database (DGIdb)LICENSEThe data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.http://www.dgidb.org/downloadsCITARINOSTAThttps://www.dgidb.org/drugs/ncit:C121641
- IUPHAR/BPS Guide to PHARMACOLOGYLICENSEThe Guide to PHARMACOLOGY database is licensed under the Open Data Commons Open Database License (ODbL) https://opendatacommons.org/licenses/odbl/. Its contents are licensed under a Creative Commons Attribution-ShareAlike 4.0 International License (http://creativecommons.org/licenses/by-sa/4.0/)https://www.guidetopharmacology.org/about.jsp#licenseGuide to Pharmacology Target Classificationhttps://www.guidetopharmacology.org/targets.jsp
- Therapeutic Target Database (TTD)Citarinostathttps://idrblab.net/ttd/data/drug/details/D01WKZ
- NCI Thesaurus (NCIt)LICENSEUnless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.https://www.cancer.gov/policies/copyright-reuseNCI Thesaurushttps://ncit.nci.nih.gov
- Open TargetsLICENSEDatasets generated by the Open Targets Platform are freely available for download.https://platform-docs.opentargets.org/licence
- KEGGLICENSEAcademic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial licensehttps://www.kegg.jp/kegg/legal.htmlTarget-based classification of drugshttp://www.genome.jp/kegg-bin/get_htext?br08310.keg
- Metabolomics Workbench
- PharosLICENSEData accessed from Pharos and TCRD is publicly available from the primary sources listed above. Please respect their individual licenses regarding proper use and redistribution.https://pharos.nih.gov/aboutcitarinostathttps://pharos.nih.gov/ligands/JUYCX2PDG4PU
- Protein Data Bank in Europe (PDBe)
- RCSB Protein Data Bank (RCSB PDB)LICENSEData files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.https://www.rcsb.org/pages/policies
- Springer Nature
- Wikidatacitarinostathttps://www.wikidata.org/wiki/Q27258687
- PubChem
- Medical Subject Headings (MeSH)LICENSEWorks produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.https://www.nlm.nih.gov/copyright.htmlcitarinostathttps://www.ncbi.nlm.nih.gov/mesh/2100185Histone Deacetylase Inhibitorshttps://www.ncbi.nlm.nih.gov/mesh/68056572
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 392810473https://pubchem.ncbi.nlm.nih.gov/substance/392810473
CONTENTS