Entinostat
Entinostat, also known as MS-275 or SNDX-275, is a potent HDAC inhibitor with potential antineoplastic activity. Entinostat binds to and inhibits histone deacetylase, an enzyme that regulates chromatin structure and gene transcription. This agent appears to exert dose-dependent effects in human leukemia cells including cyclin-dependent kinase inhibitor 1A (p21/CIP1/WAF1)-dependent growth arrest and differentiation at low drug concentrations; a marked induction of reactive oxygen species (ROS); mitochondrial damage; caspase activation; and, at higher concentrations, apoptosis.
1: Schech AJ, Shah P, Yu S, Sabnis GJ, Goloubeva O, Rosenblatt P, Kazi A, Chumsri S, Brodie A. Histone deacetylase inhibitor entinostat in combination with a retinoid downregulates HER2 and reduces the tumor initiating cell population in aromatase inhibitor-resistant breast cancer. Breast Cancer Res Treat. 2015 Jul 2. [Epub ahead of print] PubMed PMID: 26133921.
2: Ruiz R, Raez LE, Rolfo C. Entinostat (SNDX-275) for the treatment of non-small cell lung cancer. Expert Opin Investig Drugs. 2015 Aug;24(8):1101-9. doi: 10.1517/13543784.2015.1056779. Epub 2015 Jun 22. PubMed PMID: 26098363.
3: Schech A, Kazi A, Yu S, Shah P, Sabnis G. Histone Deacetylase Inhibitor Entinostat Inhibits Tumor-Initiating Cells in Triple-Negative Breast Cancer Cells. Mol Cancer Ther. 2015 Jun 2. [Epub ahead of print] PubMed PMID: 26037781.
4: Frys S, Simons Z, Hu Q, Barth MJ, Gu JJ, Mavis C, Skitzki J, Song L, Czuczman MS, Hernandez-Ilizaliturri FJ. Entinostat, a novel histone deacetylase inhibitor is active in B-cell lymphoma and enhances the anti-tumour activity of rituximab and chemotherapy agents. Br J Haematol. 2015 May;169(4):506-19. doi: 10.1111/bjh.13318. Epub 2015 Feb 23. PubMed PMID: 25712263.
5: Vendetti FP, Topper M, Huang P, Dobromilskaya I, Easwaran H, Wrangle J, Baylin SB, Poirier JT, Rudin CM. Evaluation of azacitidine and entinostat as sensitization agents to cytotoxic chemotherapy in preclinical models of non-small cell lung cancer. Oncotarget. 2015 Jan 1;6(1):56-70. PubMed PMID: 25474141; PubMed Central PMCID: PMC4381578.
6: Ngamphaiboon N, Dy GK, Ma WW, Zhao Y, Reungwetwattana T, DePaolo D, Ding Y, Brady W, Fetterly G, Adjei AA. A phase I study of the histone deacetylase (HDAC) inhibitor entinostat, in combination with sorafenib in patients with advanced solid tumors. Invest New Drugs. 2015 Feb;33(1):225-32. doi: 10.1007/s10637-014-0174-6. Epub 2014 Nov 5. PubMed PMID: 25371323.
7: Lee J, Bartholomeusz C, Mansour O, Humphries J, Hortobagyi GN, Ordentlich P, Ueno NT. A class I histone deacetylase inhibitor, entinostat, enhances lapatinib efficacy in HER2-overexpressing breast cancer cells through FOXO3-mediated Bim1 expression. Breast Cancer Res Treat. 2014 Jul;146(2):259-72. doi: 10.1007/s10549-014-3014-7. Epub 2014 Jun 12. PubMed PMID: 24916181; PubMed Central PMCID: PMC4119423.
8: Yang X, Zhang Q, Chen M, Hu L. Pharmacokinetic interaction of entinostat and lapatinib following single and co-oral administration in rats. Xenobiotica. 2014 Nov;44(11):1009-13. doi: 10.3109/00498254.2014.919431. Epub 2014 May 16. PubMed PMID: 24831712.
9: Tellez CS, Grimes MJ, Picchi MA, Liu Y, March TH, Reed MD, Oganesian A, Taverna P, Belinsky SA. SGI-110 and entinostat therapy reduces lung tumor burden and reprograms the epigenome. Int J Cancer. 2014 Nov 1;135(9):2223-31. doi: 10.1002/ijc.28865. Epub 2014 Apr 5. PubMed PMID: 24668305.
10: Prebet T, Sun Z, Figueroa ME, Ketterling R, Melnick A, Greenberg PL, Herman J, Juckett M, Smith MR, Malick L, Paietta E, Czader M, Litzow M, Gabrilove J, Erba HP, Gore SD, Tallman MS. Prolonged administration of azacitidine with or without entinostat for myelodysplastic syndrome and acute myeloid leukemia with myelodysplasia-related changes: results of the US Leukemia Intergroup trial E1905. J Clin Oncol. 2014 Apr 20;32(12):1242-8. doi: 10.1200/JCO.2013.50.3102. Epub 2014 Mar 24. PubMed PMID: 24663049; PubMed Central PMCID: PMC3986386.
2: Ruiz R, Raez LE, Rolfo C. Entinostat (SNDX-275) for the treatment of non-small cell lung cancer. Expert Opin Investig Drugs. 2015 Aug;24(8):1101-9. doi: 10.1517/13543784.2015.1056779. Epub 2015 Jun 22. PubMed PMID: 26098363.
3: Schech A, Kazi A, Yu S, Shah P, Sabnis G. Histone Deacetylase Inhibitor Entinostat Inhibits Tumor-Initiating Cells in Triple-Negative Breast Cancer Cells. Mol Cancer Ther. 2015 Jun 2. [Epub ahead of print] PubMed PMID: 26037781.
4: Frys S, Simons Z, Hu Q, Barth MJ, Gu JJ, Mavis C, Skitzki J, Song L, Czuczman MS, Hernandez-Ilizaliturri FJ. Entinostat, a novel histone deacetylase inhibitor is active in B-cell lymphoma and enhances the anti-tumour activity of rituximab and chemotherapy agents. Br J Haematol. 2015 May;169(4):506-19. doi: 10.1111/bjh.13318. Epub 2015 Feb 23. PubMed PMID: 25712263.
5: Vendetti FP, Topper M, Huang P, Dobromilskaya I, Easwaran H, Wrangle J, Baylin SB, Poirier JT, Rudin CM. Evaluation of azacitidine and entinostat as sensitization agents to cytotoxic chemotherapy in preclinical models of non-small cell lung cancer. Oncotarget. 2015 Jan 1;6(1):56-70. PubMed PMID: 25474141; PubMed Central PMCID: PMC4381578.
6: Ngamphaiboon N, Dy GK, Ma WW, Zhao Y, Reungwetwattana T, DePaolo D, Ding Y, Brady W, Fetterly G, Adjei AA. A phase I study of the histone deacetylase (HDAC) inhibitor entinostat, in combination with sorafenib in patients with advanced solid tumors. Invest New Drugs. 2015 Feb;33(1):225-32. doi: 10.1007/s10637-014-0174-6. Epub 2014 Nov 5. PubMed PMID: 25371323.
7: Lee J, Bartholomeusz C, Mansour O, Humphries J, Hortobagyi GN, Ordentlich P, Ueno NT. A class I histone deacetylase inhibitor, entinostat, enhances lapatinib efficacy in HER2-overexpressing breast cancer cells through FOXO3-mediated Bim1 expression. Breast Cancer Res Treat. 2014 Jul;146(2):259-72. doi: 10.1007/s10549-014-3014-7. Epub 2014 Jun 12. PubMed PMID: 24916181; PubMed Central PMCID: PMC4119423.
8: Yang X, Zhang Q, Chen M, Hu L. Pharmacokinetic interaction of entinostat and lapatinib following single and co-oral administration in rats. Xenobiotica. 2014 Nov;44(11):1009-13. doi: 10.3109/00498254.2014.919431. Epub 2014 May 16. PubMed PMID: 24831712.
9: Tellez CS, Grimes MJ, Picchi MA, Liu Y, March TH, Reed MD, Oganesian A, Taverna P, Belinsky SA. SGI-110 and entinostat therapy reduces lung tumor burden and reprograms the epigenome. Int J Cancer. 2014 Nov 1;135(9):2223-31. doi: 10.1002/ijc.28865. Epub 2014 Apr 5. PubMed PMID: 24668305.
10: Prebet T, Sun Z, Figueroa ME, Ketterling R, Melnick A, Greenberg PL, Herman J, Juckett M, Smith MR, Malick L, Paietta E, Czader M, Litzow M, Gabrilove J, Erba HP, Gore SD, Tallman MS. Prolonged administration of azacitidine with or without entinostat for myelodysplastic syndrome and acute myeloid leukemia with myelodysplasia-related changes: results of the US Leukemia Intergroup trial E1905. J Clin Oncol. 2014 Apr 20;32(12):1242-8. doi: 10.1200/JCO.2013.50.3102. Epub 2014 Mar 24. PubMed PMID: 24663049; PubMed Central PMCID: PMC3986386.
| Chemical | |
|---|---|
| CAS Num | 209783-80-2 |
| Chemical Formula | C21H20N4O3 |
| Molecular Weight | 376.41 |
| IUPAC Chemical Name | pyridin-3-ylmethyl 4-((2-aminophenyl)carbamoyl)benzylcarbamate. |
| Exact Mass | 376.15354 |
| Elemental Analysis | C, 67.01; H, 5.36; N, 14.88; O, 12.75 |
| Synonym | MS275; MS-275; MS 2275; SNDX275; SNDX-275; SNDX 275; Entinostat |
| Solubility | Soluble in DMSO, not in water |
| SMILES Code | O=C(OCC1=CC=CN=C1)NCC2=CC=C(C(NC3=CC=CC=C3N)=O)C=C2 |
| Biological | |
| Targets and Effects | cyclin-dependent kinase |
| Pathways | Apoptosis |
| Physical | |
| Appearance | white off white solid powder |
| Purity | >98% (or refer to the Certificate of Analysis) |
| Shipping Condition | Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs. |
| Storage Condition | Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). |
| Shelf Life | >2 years if stored properly |
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