entinostat   Click here for help

GtoPdb Ligand ID: 7007

Synonyms: BAY 86-5274 | MS-275 | SNDX-275 | ZK 244894
Compound class: Synthetic organic
Comment: Entinostat (MS-275) inhibits Class I histone deacetylases (HDACs 1, 2, 3 & 8), but has been shown to be somewhat selective for HDAC1 [1,4]. Studies in rodent models of inflammation suggest that inhibition by entinostat may be clinically useful [2,6-8], perhaps more so than broader acting Class I HDAC inhibitors such as vorinostat (SAHA) [6].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 3
Rotatable bonds 9
Topological polar surface area 106.34
Molecular weight 376.15
XLogP 2.2
No. Lipinski's rules broken 0
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Canonical SMILES O=C(OCc1cccnc1)NCc1ccc(cc1)C(=O)Nc1ccccc1N
Isomeric SMILES O=C(OCc1cccnc1)NCc1ccc(cc1)C(=O)Nc1ccccc1N
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)
1. Bradner JE, West N, Grachan ML, Greenberg EF, Haggarty SJ, Warnow T, Mazitschek R. (2010)
Chemical phylogenetics of histone deacetylases.
Nat Chem Biol, 6 (3): 238-243. [PMID:20139990]
2. Cantley MD, Bartold PM, Marino V, Fairlie DP, Le GT, Lucke AJ, Haynes DR. (2011)
Histone deacetylase inhibitors and periodontal bone loss.
J Periodont Res, 46 (6): 697-703. [PMID:21745207]
3. Dear AE. (2016)
Epigenetic Modulators and the New Immunotherapies.
N Engl J Med, 374 (7): 684-6. [PMID:26886527]
4. Hu E, Dul E, Sung CM, Chen Z, Kirkpatrick R, Zhang GF, Johanson K, Liu R, Lago A, Hofmann G et al.. (2003)
Identification of novel isoform-selective inhibitors within class I histone deacetylases.
J Pharmacol Exp Ther, 307 (2): 720-8. [PMID:12975486]
5. Khan N, Jeffers M, Kumar S, Hackett C, Boldog F, Khramtsov N, Qian X, Mills E, Berghs SC, Carey N et al.. (2008)
Determination of the class and isoform selectivity of small-molecule histone deacetylase inhibitors.
Biochem J, 409 (2): 581-9. [PMID:17868033]
6. Lin HS, Hu CY, Chan HY, Liew YY, Huang HP, Lepescheux L, Bastianelli E, Baron R, Rawadi G, Clément-Lacroix P. (2007)
Anti-rheumatic activities of histone deacetylase (HDAC) inhibitors in vivo in collagen-induced arthritis in rodents.
Br J Pharmacol, 150 (7): 862-72. [PMID:17325656]
7. Zhang ZY, Schluesener HJ. (2012)
HDAC inhibitor MS-275 attenuates the inflammatory reaction in rat experimental autoimmune prostatitis.
Prostate, 72 (1): 90-9. [PMID:21538420]
8. Zhang ZY, Zhang Z, Schluesener HJ. (2010)
MS-275, an histone deacetylase inhibitor, reduces the inflammatory reaction in rat experimental autoimmune neuritis.
Neuroscience, 169 (1): 370-7. [PMID:20451583]