Entinostat

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Entinostat
Names
Preferred IUPAC name
(Pyridin-3-yl)methyl ({4-[(2-aminophenyl)carbamoyl]phenyl}methyl)carbamate
Other names
SNDX-275; MS-275
Identifiers
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.158.999 Edit this at Wikidata
IUPHAR/BPS
KEGG
UNII
  • 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) ☒N
    Key: INVTYAOGFAGBOE-UHFFFAOYSA-N ☒N
  • 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)
    Key: INVTYAOGFAGBOE-UHFFFAOYAU
  • C1=CC=C(C(=C1)N)NC(=O)C2=CC=C(C=C2)CNC(=O)OCC3=CN=CC=C3
Properties
C21H20N4O3
Molar mass 376.4085 g/mol
Pharmacology
L01XH05 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Entinostat, also known as SNDX-275 and MS-275, is a benzamide histone deacetylase inhibitor undergoing clinical trials for treatment of various cancers.[1][2][3][4]

Entinostat inhibits class I HDAC1 and HDAC3 with IC50 of 0.51 μM and 1.7 μM, respectively.[5]

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.[6]

It has also been investigated as a potential male contraceptive drug.[7]

References

  1. doi:10.1200/jco.2008.26.15_suppl.19036
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  2. S2CID 219169967
    .
  3. S2CID 235378858
    .
  4. PMID 36969235
    .
  5. ^ US 2009/0263353, Maier T, Beckers T, Hummel RP, Feth M, Muller M, Bar T, Volz J, "Novel Sulphonylpyrroles as Inhibitors of Hdac S Novel Sulphonylpyrroles", issued 31 July 2012, assigned to 4SC AG 
  6. ^ "Company Prepares for Pivotal Phase 3 Study of Entinostat, Most Advanced HDAC Inhibitor in Development for ER+ Metastatic Breast Cancer" (PDF). Syndax Pharmaceuticals. 27 August 2013. Archived from the original (PDF) on 17 June 2016.
  7. PMID 38377195
    .
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