Entinostat

Entinostat

Names
IUPAC names Pyridin-3-ylmethyl N-[[4-[(2-aminophenyl)carbamoyl]phenyl] methyl]carbamate
Other names SNDX-275; MS-275
Identifiers
CAS Number	209783-80-2
ChEMBL	ChEMBL27759
ChemSpider	4111
IUPHAR/BPS	7007
Jmol interactive 3D	Image
KEGG	D09338
PubChem	4261
UNII	1ZNY4FKK9H
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) Key: INVTYAOGFAGBOE-UHFFFAOYSA-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
SMILES C1=CC=C(C(=C1)N)NC(=O)C2=CC=C(C=C2)CNC(=O)OCC3=CN=CC=C3
Properties
Chemical formula	C21H20N4O3
Molar mass	376.4085 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
verify (what is  ?)
Infobox references

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

Entinostat inhibits class I HDAC1 and HDAC3 with IC₅₀ of 0.51 μM and 1.7 μM, respectively.^[2]

Clinical trials

There is an ongoing phase II trial studying the effect of entinostat on Hodgkin's lymphoma.^[3] It is in other phase II trials for advanced breast cancer (in combination with aromatase inhibitors)^[4] and for metastatic lung cancer (in combination with erlotinib).^[5] As of September 2013, the Food and Drug Administration is working with the industry to design phase III clinical trials. They seek to evaluate the application of Entinostat for the reduction, or prevention of, treatment resistance to aromatase inhibitors in hormone receptor positive breast cancer.^[6] 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.^[7]

References

1. Phase I trial of 5-azacitidine (5AC) and SNDX-275 in advanced lung cancer (NSCLC)
2. Novel Sulphonylpyrroles as Inhibitors of Hdac S Novel Sulphonylpyrroles
3. A Phase 2 Multi-Center Study of Entinostat (SNDX-275) in Patient With Relapsed or Refractory Hodgkin's Lymphoma
4. A Phase 2, Multicenter Study of the Effect of the Addition of SNDX-275 to Continued Aromatase Inhibitor (AI) Therapy in Postmenopausal Women With ER+ Breast Cancer Whose Disease is Progressing
5. A Phase 2 Exploratory Study of Erlotinib and SNDX-275 in Patients With Non-small Cell Lung Carcinoma Who Are Progressing on Erlotinib
6. Breakthrough Designation Granted to Entinostat for Advanced Breast Cancer Silas Inman Published Online: Wednesday, September 11, 2013 http://www.onclive.com/web-exclusives/Breakthrough-Designation-Granted-to-Entinostat-for-Advanced-Breast-Cancer
7. http://www.syndax.com/assets/130827%20Syndax%20Series%20B%20news%20release.pdf