Entinostat

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| ImageFile = Entinostat.svg

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| PIN = (Pyridin-3-yl)methyl ({4-[(2-aminophenyl)carbamoyl]phenyl}methyl)carbamate

| OtherNames = SNDX-275; MS-275

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Entinostat, also known as SNDX-275 and MS-275, is a benzamide histone deacetylase inhibitor undergoing clinical trials for treatment of various cancers.{{cite journal | vauthors = Juergens RA, Vendetti F, Coleman B, Sebree RS, Rudek MA, Belinsky SA, Brock MV, Herman JG, Baylin SB, Rudin CM | display-authors = 6 | title = Phase I trial of 5-azacitidine (5AC) and SNDX-275 in advanced lung cancer (NSCLC). | journal = Journal of Clinical Oncology | date = May 2008 | volume = 26 | issue = 15_suppl | page = 19036- | doi = 10.1200/jco.2008.26.15_suppl.19036 }}{{cite book | vauthors = Kiany S, Harrison D, Gordon N | title = Current Advances in Osteosarcoma | chapter = The Histone Deacetylase Inhibitor Entinostat/Syndax 275 in Osteosarcoma | series = Advances in Experimental Medicine and Biology | date = 2020 | volume = 1257 | pages = 75–83 | doi = 10.1007/978-3-030-43032-0_7 | pmid = 32483732 | isbn = 978-3-030-43031-3 | s2cid = 219169967 }}{{cite journal | vauthors = Wang Y, Xie Q, Tan H, Liao M, Zhu S, Zheng LL, Huang H, Liu B | display-authors = 6 | title = Targeting cancer epigenetic pathways with small-molecule compounds: Therapeutic efficacy and combination therapies | journal = Pharmacological Research | volume = 173 | pages = 105702 | date = November 2021 | doi = 10.1016/j.phrs.2021.105702 | pmid = 34102228 | s2cid = 235378858 }}{{cite journal | vauthors = Lian B, Chen X, Shen K | title = Inhibition of histone deacetylases attenuates tumor progression and improves immunotherapy in breast cancer | journal = Frontiers in Immunology | date = 2023 | volume = 14 | pages = 1164514 | doi = 10.3389/fimmu.2023.1164514 | doi-access = free | pmid = 36969235 | pmc = 10034161 }}

Entinostat inhibits class I HDAC1 and HDAC3 with IC₅₀ of 0.51 μM and 1.7 μM, respectively.{{cite patent | url = https://patents.google.com/patent/US20090263353A1 | country = US | number = 2009/0263353 | title = Novel Sulphonylpyrroles as Inhibitors of Hdac S Novel Sulphonylpyrroles | inventor = Maier T, Beckers T, Hummel RP, Feth M, Muller M, Bar T, Volz J | assign = 4SC AG | gdate = 31 July 2012 }}

Syndax pharmaceuticals currently holds the rights to entinostat and recently received $26.6 million in funds to advance treatments of resistant cancers using epigenetic tools.{{cite web | url = http://www.syndax.com/assets/130827%20Syndax%20Series%20B%20news%20release.pdf | archive-url = https://web.archive.org/web/20160617004219/http://www.syndax.com/wp-content/uploads/2015/12/Syndax-Pharmaceuticals-Secures-26.6-Million-Series-B-Financing-for.pdf | archive-date = 17 June 2016 | title = Company Prepares for Pivotal Phase 3 Study of Entinostat, Most Advanced HDAC Inhibitor in Development for ER+ Metastatic Breast Cancer | work = Syndax Pharmaceuticals | date = 27 August 2013 }}

It has also been investigated as a potential male contraceptive drug.{{cite journal | vauthors = Hong SH, Castro G, Wang D, Nofsinger R, Kane M, Folias A, Atkins AR, Yu RT, Napoli JL, Sassone-Corsi P, de Rooij DG, Liddle C, Downes M, Evans RM | display-authors = 6 | title = Targeting nuclear receptor corepressors for reversible male contraception | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 121 | issue = 9 | pages = e2320129121 | date = February 2024 | pmid = 38377195 | doi = 10.1073/pnas.2320129121 | doi-access = free }}