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MedKoo Cat#: 109736 | Name: Tazemetostat mesylate

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Tazemetostat (EPZ-6438, E7438) is a potent, selective, and orally bioavailable small-molecule inhibitor of enhancer of zeste homolog 2 (EZH2), a histone methyltransferase involved in epigenetic gene silencing. It inhibits both wild-type and mutant EZH2 (e.g., Y641 and A677 mutations) with nanomolar potency—IC₅₀ values of 2.5 nM (Y641N), 11 nM (Y641F), and 4.7 nM (wild-type EZH2) in biochemical assays. In cellular models, Tazemetostat leads to a reduction in trimethylation of histone H3 at lysine 27 (H3K27me3) and induces antiproliferative effects in EZH2-mutant diffuse large B-cell lymphoma (DLBCL) and follicular lymphoma cells. In xenograft models, oral administration of Tazemetostat significantly reduces tumor growth with favorable pharmacokinetic properties and minimal toxicity. These properties support its clinical development, and it is currently FDA-approved for certain relapsed/refractory follicular lymphomas and epithelioid sarcomas.

Chemical Structure

Tazemetostat mesylate
Tazemetostat mesylate
CAS#Tazemetostat mesylate

Theoretical Analysis

MedKoo Cat#: 109736

Name: Tazemetostat mesylate

CAS#: Tazemetostat mesylate

Chemical Formula: C35H48N4O7S

Exact Mass: 0.0000

Molecular Weight: 668.85

Elemental Analysis: C, 62.85; H, 7.23; N, 8.38; O, 16.74; S, 4.79

Price and Availability

Related CAS #
1467052-84-1 (HCl) 1467052-75-0 (HBr) 1403254-99-8 (free base) Tazemetostat mesylate
Synonym
EPZ-6438; EPZ 6438; EPZ6438; E7438; E-7438; E 7438; Tazemetostat mesylate
IUPAC/Chemical Name
N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-5-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-4-methyl-4'-(morpholinomethyl)-[1,1'-biphenyl]-3-carboxamide, mesylate
InChi Key
JDPYIWQACYKRRW-UHFFFAOYSA-N
InChi Code
InChI=1S/C34H44N4O4.CH4O3S/c1-5-38(29-10-14-41-15-11-29)32-20-28(27-8-6-26(7-9-27)22-37-12-16-42-17-13-37)19-30(25(32)4)33(39)35-21-31-23(2)18-24(3)36-34(31)40;1-5(2,3)4/h6-9,18-20,29H,5,10-17,21-22H2,1-4H3,(H,35,39)(H,36,40);1H3,(H,2,3,4)
SMILES Code
O=C(C1=CC(C2=CC=C(CN3CCOCC3)C=C2)=CC(N(CC)C4CCOCC4)=C1C)NCC5=C(C)C=C(C)NC5=O.OS(=O)(C)=O
Appearance
To be determined
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).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 668.85 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Orleni M, Beumer JH. Pharmacology and pharmacokinetics of tazemetostat. Cancer Chemother Pharmacol. 2024 May;93(5):509-517. doi: 10.1007/s00280-024-04658-4. Epub 2024 Mar 23. PMID: 38520556. 2: Anestopoulos I, Paraskevaidis I, Kyriakou S, Giova LE, Trafalis DT, Botaitis S, Franco R, Pappa A, Panayiotidis MI. Isothiocyanates Potentiate Tazemetostat- Induced Apoptosis by Modulating the Expression of Apoptotic Genes, Members of Polycomb Repressive Complex 2, and Levels of Tri-Methylating Lysine 27 at Histone 3 in Human Malignant Melanoma Cells. Int J Mol Sci. 2024 Feb 27;25(5):2745. doi: 10.3390/ijms25052745. PMID: 38473991; PMCID: PMC10931595. 3: Vejmelkova K, Pokorna P, Noskova K, Faustmannova A, Drabova K, Pavelka Z, Bajciova V, Broz M, Tinka P, Jezova M, Palova H, Kren L, Valik D, Slaby O, Sterba J. Tazemetostat in the therapy of pediatric INI1-negative malignant rhabdoid tumors. Sci Rep. 2023 Dec 7;13(1):21623. doi: 10.1038/s41598-023-48774-2. PMID: 38062114; PMCID: PMC10703767. 4: Amin MN, El-Far YM, El-Mowafy M, Elgaml A. Tazemetostat decreases β-catenin and CD13 protein expression in HEPG-2 and Hepatitis B virus-transfected HEPG-2 with decreased cell viability. Clin Epigenetics. 2023 Nov 8;15(1):180. doi: 10.1186/s13148-023-01593-8. PMID: 37941056; PMCID: PMC10634085. 5: Chen L, Zheng X, Liu W, Sun Y, Zhao S, Tian L, Tian W, Xue F, Kang C, Wang Y. Compound AC1Q3QWB upregulates CDKN1A and SOX17 by interrupting the HOTAIR-EZH2 interaction and enhances the efficacy of tazemetostat in endometrial cancer. Cancer Lett. 2023 Dec 1;578:216445. doi: 10.1016/j.canlet.2023.216445. Epub 2023 Oct 20. PMID: 37866545. 6: Chen X, Wu J, Pang G, Wei S, Wang P. Integrase Interactor 1 (INI1) Deficiency in a Lung Cancer Patient Presents Nonresponse to Immunotherapy and Tazemetostat: A Case Report. Cureus. 2023 Aug 4;15(8):e42934. doi: 10.7759/cureus.42934. PMID: 37667707; PMCID: PMC10475322. 7: Budagaga Y, Sabet Z, Zhang Y, Novotná E, Hanke I, Rozkoš T, Hofman J. Tazemetostat synergistically combats multidrug resistance by the unique triple inhibition of ABCB1, ABCC1, and ABCG2 efflux transporters in vitro and ex vivo. Biochem Pharmacol. 2023 Oct;216:115769. doi: 10.1016/j.bcp.2023.115769. Epub 2023 Aug 25. PMID: 37634597. 8: Ding N, You A, Zhao S, Yang H, Lai C, Ye F. EZH2 inhibitor Tazemetostat synergizes with JQ-1 in esophageal cancer by inhibiting c-Myc signaling pathway. Med Oncol. 2023 Aug 27;40(10):281. doi: 10.1007/s12032-023-02147-x. PMID: 37634215. 9: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Tazemetostat. 2023 Aug 4. PMID: 37643279. 10: Chi SN, Yi JS, Williams PM, Roy-Chowdhuri S, Patton DR, Coffey BD, Reid JM, Piao J, Saguilig L, Alonzo TA, Berg SL, Ramirez NC, Jaju A, Mhlanga JC, Fox E, Hawkins DS, Mooney MM, Takebe N, Tricoli JV, Janeway KA, Seibel NL, Parsons DW. Tazemetostat for tumors harboring SMARCB1/SMARCA4 or EZH2 alterations: results from NCI-COG pediatric MATCH APEC1621C. J Natl Cancer Inst. 2023 Nov 8;115(11):1355-1363. doi: 10.1093/jnci/djad085. PMID: 37228094; PMCID: PMC11009504. 11: Bekric D, Neureiter D, Ablinger C, Dobias H, Beyreis M, Ritter M, Jakab M, Bischof J, Koller U, Kiesslich T, Mayr C. Evaluation of Tazemetostat as a Therapeutically Relevant Substance in Biliary Tract Cancer. Cancers (Basel). 2023 Mar 2;15(5):1569. doi: 10.3390/cancers15051569. PMID: 36900361; PMCID: PMC10000745. 12: Chu L, Tan D, Zhu M, Qu Y, Ma X, Song BL, Qi W. EZH2 W113C is a gain-of- function mutation in B-cell lymphoma enabling both PRC2 methyltransferase activation and tazemetostat resistance. J Biol Chem. 2023 Apr;299(4):103073. doi: 10.1016/j.jbc.2023.103073. Epub 2023 Feb 27. PMID: 36858198; PMCID: PMC10066557. 13: Hou Y, Zak J, Shi Y, Pratumchai I, Dinner B, Wang W, Qin K, Weber E, Teijaro JR, Wu P. Transient EZH2 suppression by Tazemetostat during in vitro expansion maintains T cell stemness and improves adoptive T cell therapy. bioRxiv [Preprint]. 2023 Feb 7:2023.02.07.527459. doi: 10.1101/2023.02.07.527459. PMID: 36798389; PMCID: PMC9934551. 14: Zhang Q, Chen X, Cao J, Yang W, Wan G, Feng Q, Zhou S, Yang H, Wang N, Liu Z, Xiao H, Zhu Y, Yu L. Discovery of a Novel Covalent EZH2 Inhibitor Based on Tazemetostat Scaffold for the Treatment of Ovarian Cancer. J Med Chem. 2023 Feb 9;66(3):1725-1741. doi: 10.1021/acs.jmedchem.2c01370. Epub 2023 Jan 24. PMID: 36692394. 15: Li H, Wang YJ, Geng XN, Kang YR, Wang YL, Qiu XJ. Pharmacokinetics of Herb- Drug Interactions of Plumbagin and Tazemetostat in Rats by UPLC-MS/MS. Drug Des Devel Ther. 2022 Sep 29;16:3385-3394. doi: 10.2147/DDDT.S384156. PMID: 36199632; PMCID: PMC9529013. 16: Saleh K, Classe M, Nguyen F, Moya-Plana A, Even C. Tazemetostat for the treatment of INI-1-deficient sinonasal tumor. Eur J Cancer. 2022 Sep;172:329-331. doi: 10.1016/j.ejca.2022.06.032. Epub 2022 Jul 9. PMID: 35820243. 17: Tazemetostat Shows Antitumor Activity in Malignant Pleural Mesothelioma. Cancer Discov. 2022 Jul 6;12(7):1610. doi: 10.1158/2159-8290.CD-RW2022-096. PMID: 35621347. 18: Zauderer MG, Szlosarek PW, Le Moulec S, Popat S, Taylor P, Planchard D, Scherpereel A, Koczywas M, Forster M, Cameron RB, Peikert T, Argon EK, Michaud NR, Szanto A, Yang J, Chen Y, Kansra V, Agarwal S, Fennell DA. EZH2 inhibitor tazemetostat in patients with relapsed or refractory, BAP1-inactivated malignant pleural mesothelioma: a multicentre, open-label, phase 2 study. Lancet Oncol. 2022 Jun;23(6):758-767. doi: 10.1016/S1470-2045(22)00277-7. Epub 2022 May 16. PMID: 35588752. 19: Proudman DG, Gupta D, Nellesen D, Yang J, Kamp BA, Mamlouk K, Cheson BD. Tazemetostat in relapsed/refractory follicular lymphoma: a propensity score- matched analysis of E7438-G000-101 trial outcomes. Oncotarget. 2022 May 11;13:677-683. doi: 10.18632/oncotarget.28229. PMID: 35574216; PMCID: PMC9093865. 20: Straining R, Eighmy W. Tazemetostat: EZH2 Inhibitor. J Adv Pract Oncol. 2022 Mar;13(2):158-163. doi: 10.6004/jadpro.2022.13.2.7. Epub 2022 Mar 25. PMID: 35369397; PMCID: PMC8955562.

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