| Revision as of 22:03, 11 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per [[Misplaced Pages:WikiProject Chemicals/Chembox validation|Chem/Drug← Previous edit |
Latest revision as of 12:36, 23 September 2024 edit undoTom.Reding (talk | contribs)Autopatrolled, Extended confirmed users, Page movers, Template editors3,861,616 editsm WP:STUBSPACING followupTag: AWB |
| (45 intermediate revisions by 31 users not shown) |
| Line 1: |
Line 1: |
|
{{chembox |
|
{{chembox |
|
|
| Verifiedfields = changed |
|
|
| Watchedfields = changed |
|
⚫ |
| verifiedrevid = 444340516 |
|
⚫ |
| ImageFile = Entinostat.svg |
|
⚫ |
| ImageSize = 260 |
|
⚫ |
| PIN = (Pyridin-3-yl)methyl ({4-phenyl}methyl)carbamate |
|
⚫ |
| OtherNames = SNDX-275; MS-275 |
|
⚫ |
|Section1={{Chembox Identifiers |
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
| UNII = 1ZNY4FKK9H |
|
| UNII = 1ZNY4FKK9H |
|
|
| IUPHAR_ligand = 7007 |
| ⚫ |
| verifiedrevid = 437134752 |
|
|
|
| CASNo_Ref = {{cascite|correct|??}} |
| ⚫ |
|ImageFile=Entinostat.png |
|
|
⚫ |
| CASNo=209783-80-2 |
| ⚫ |
|ImageSize=200px |
|
|
⚫ |
| PubChem=4261 |
| ⚫ |
|IUPACName=Pyridin-3-ylmethyl ''N''-<nowiki>phenyl]methyl]carbamate |
|
| ⚫ |
|OtherNames=SNDX-275; MS-275 |
|
| ⚫ |
|Section1={{Chembox Identifiers |
|
| ⚫ |
| CASNo=209783-80-2 |
|
| ⚫ |
| PubChem=4261 |
|
|
| KEGG_Ref = {{keggcite|correct|kegg}} |
|
| KEGG_Ref = {{keggcite|correct|kegg}} |
|
| KEGG = D09338 |
|
| KEGG = D09338 |
|
|
| ChEBI_Ref = {{ebicite|changed|EBI}} |
| ⚫ |
| SMILES=C1=CC=C(C(=C1)N)NC(=O)C2=CC=C(C=C2)CNC(=O)OCC3=CN=CC=C3 |
|
|
|
| ChEBI = 132082 |
|
|
| ChEMBL_Ref = {{ebicite|changed|EBI}} |
|
|
| ChEMBL = 27759 |
|
⚫ |
| SMILES=C1=CC=C(C(=C1)N)NC(=O)C2=CC=C(C=C2)CNC(=O)OCC3=CN=CC=C3 |
|
|
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
|
|
| ChemSpiderID = 4111 |
|
|
| InChI = 1/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) |
|
|
| InChIKey = INVTYAOGFAGBOE-UHFFFAOYAU |
|
|
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
|
|
| StdInChI = 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) |
|
|
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
|
|
| StdInChIKey = INVTYAOGFAGBOE-UHFFFAOYSA-N |
|
}} |
|
}} |
|
|Section2={{Chembox Properties |
|
|Section2={{Chembox Properties |
|
| Formula=C<sub>21</sub>H<sub>20</sub>N<sub>4</sub>O<sub>3</sub> |
|
| Formula=C<sub>21</sub>H<sub>20</sub>N<sub>4</sub>O<sub>3</sub> |
|
| MolarMass=376.4085 |
|
| MolarMass=376.4085 g/mol |
|
| Appearance= |
|
| Appearance= |
|
| Density= |
|
| Density= |
|
| MeltingPt= |
|
| MeltingPt= |
|
| BoilingPt= |
|
| BoilingPt= |
|
| Solubility= |
|
| Solubility= |
|
}} |
|
}} |
|
|Section3={{Chembox Hazards |
|
|Section3={{Chembox Hazards |
|
| MainHazards= |
|
| MainHazards= |
|
| FlashPt= |
|
| FlashPt= |
|
|
| AutoignitionPt = |
|
| Autoignition= |
|
|
|
}} |
|
|
| Section5 = {{Chembox Pharmacology |
|
|
| ATCCode_prefix = L01 |
|
|
| ATCCode_suffix = XH05 |
|
}} |
|
}} |
|
}} |
|
}} |
|
|
|
|
|
|
'''Entinostat''', also known as '''SNDX-275''' and '''MS-275''', is a ] ] undergoing clinical trials for treatment of various cancers.<ref>{{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 }}</ref><ref>{{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 }}</ref><ref>{{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 }}</ref><ref>{{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 }}</ref> |
|
'''Entinostat''', also known as '''SNDX-275''' and '''MS-275''', is a ] ] undergoing clinical trials for treatment of various cancers.<ref></ref> |
|
|
|
|
|
|
Entinostat inhibits class I ] and ] with ] of 0.51 μM and 1.7 μM, respectively.<ref> |
|
Entinostat inhibits class I ] and ] with ] of 0.51 μM and 1.7 μM, respectively.<ref>{{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 }}</ref> |
|
|
|
|
|
|
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.<ref>{{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 }}</ref> |
|
==Clinical trials== |
|
|
There is an ongoing phase II trial studying the effect of entinostat on ].<ref></ref> |
|
|
It is in other phase II trials for advanced ] (in combination with ]s)<ref></ref> and for metastatic ] (in combination with erlotinib)<ref></ref>. |
|
|
|
|
|
|
|
It has also been investigated as a potential ] drug.<ref name="pmid38377195">{{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 }}</ref> |
| ⚫ |
==References== |
|
|
{{reflist}} |
|
|
|
|
|
|
⚫ |
== References == |
|
|
{{Reflist}} |
|
|
|
|
|
|
{{Chemotherapeutic agents}} |
|
{{pharma-stub}} |
|
|
|
{{HDAC inhibitors}} |
|
|
|
|
| ⚫ |
] |
|
| ⚫ |
] |
|
|
] |
|
] |
|
⚫ |
] |
|
|
] |
|
|
] |
|
⚫ |
] |
|
|
|
|
|
|
|
|
{{antineoplastic-drug-stub}} |