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MedKoo Cat#: 145716 | Name: Ezobresib HCl

Description:

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

Ezobresib, also known as BMS-986158 is a potent and selective BET inhibitor. BMS-986158 binds to the acetyl-lysine binding site in the BRD of BET proteins, thereby preventing the interaction between BET proteins and acetylated histones. This disrupts chromatin remodeling and prevents the expression of certain growth-promoting genes, resulting in an inhibition of tumor cell growth. BET proteins (BRD2, BRD3, BRD4 and BRDT) are transcriptional regulators that bind to acetylated lysines on the tails of histones H3 and H4, and regulate chromatin structure and function; they play an important role in the modulation of gene expression during development and cellular growth.

Chemical Structure

Ezobresib HCl
Ezobresib HCl
CAS#Ezobresib HCl

Theoretical Analysis

MedKoo Cat#: 145716

Name: Ezobresib HCl

CAS#: Ezobresib HCl

Chemical Formula: C30H33N5O2

Exact Mass: 495.2600

Molecular Weight: 495.63

Elemental Analysis: C, 72.70; H, 6.71; N, 14.13; O, 6.46

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
Ezobresib HCl 1800340-40-2 (free base)
Synonym
Ezobresib; BMS-986158;
IUPAC/Chemical Name
(S)-2-(3-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5-(phenyl(tetrahydro-2H-pyran-4-yl)methyl)-5H-pyrido[3,2-b]indol-7-yl)propan-2-ol
InChi Key
KGERZPVQIRYWRK-GDLZYMKVSA-N
InChi Code
1S/C30H33N5O2/c1-19-28(34(4)33-32-19)22-16-26-27(31-18-22)24-11-10-23(30(2,3)36)17-25(24)35(26)29(20-8-6-5-7-9-20)21-12-14-37-15-13-21/h5-11,16-18,21,29,36H,12-15H2,1-4H3/t29-/m1/s1
SMILES Code
CN1N=NC(C)=C1C2=CN=C3C(=C2)N([C@@H](C4CCOCC4)C5=CC=CC=C5)C6=C3C=CC(=C6)C(C)(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 495.63 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: Cheng ML, Huang Y, Luong N, LoPiccolo J, Nishino M, Sholl LM, Chirieac LR, Santucci AD, Rabin MS, Jänne PA, Coker S, Diamond JR, Hilton J, Shapiro GI, French CA. Exceptional Response to Bromodomain and Extraterminal Domain Inhibitor Therapy With BMS-986158 in BRD4-NUTM1 NUT Carcinoma Harboring a BRD4 Splice Site Mutation. JCO Precis Oncol. 2023 Jun;7:e2200633. doi: 10.1200/PO.22.00633. PMID: 37384867; PMCID: PMC10581614. 2: Rana M, Kansal RG, Bisunke B, Fang J, Shibata D, Bajwa A, Yang J, Glazer ES. Bromo- and Extra-Terminal Domain Inhibitors Induce Mitochondrial Stress in Pancreatic Ductal Adenocarcinoma. Mol Cancer Ther. 2023 Aug 1;22(8):936-946. doi: 10.1158/1535-7163.MCT-23-0149. PMID: 37294884; PMCID: PMC10527726. 3: Chin DH, Osman I, Porch J, Kim H, Buck KK, Rodriguez J, Carapia B, Yan D, Moura SB, Sperry J, Nakashima J, Altman K, Altman D, Gryder BE. BET Bromodomain Degradation Disrupts Function but Not 3D Formation of RNA Pol2 Clusters. Pharmaceuticals (Basel). 2023 Jan 29;16(2):199. doi: 10.3390/ph16020199. PMID: 37259348; PMCID: PMC9966215. 4: Hilton J, Cristea M, Postel-Vinay S, Baldini C, Voskoboynik M, Edenfield W, Shapiro GI, Cheng ML, Vuky J, Corr B, Das S, Apfel A, Xu K, Kozicki M, Ünsal- Kaçmaz K, Hammell A, Wang G, Ravindran P, Kollia G, Esposito O, Coker S, Diamond JR. BMS-986158, a Small Molecule Inhibitor of the Bromodomain and Extraterminal Domain Proteins, in Patients with Selected Advanced Solid Tumors: Results from a Phase 1/2a Trial. Cancers (Basel). 2022 Aug 23;14(17):4079. doi: 10.3390/cancers14174079. PMID: 36077617; PMCID: PMC9454848. 5: Huang XS, Tian RR, Ma MD, Luo RH, Yang LM, Peng GH, Zhang M, Dong XQ, Zheng YT. Bromodomain and Extra-Terminal Inhibitor BMS-986158 Reverses Latent HIV-1 Infection In Vitro and Ex Vivo by Increasing CDK9 Phosphorylation and Recruitment. Pharmaceuticals (Basel). 2022 Mar 10;15(3):338. doi: 10.3390/ph15030338. PMID: 35337136; PMCID: PMC8952190. 6: Gavai AV, Norris D, Delucca G, Tortolani D, Tokarski JS, Dodd D, O'Malley D, Zhao Y, Quesnelle C, Gill P, Vaccaro W, Huynh T, Ahuja V, Han WC, Mussari C, Harikrishnan L, Kamau M, Poss M, Sheriff S, Yan C, Marsilio F, Menard K, Wen ML, Rampulla R, Wu DR, Li J, Zhang H, Li P, Sun D, Yip H, Traeger SC, Zhang Y, Mathur A, Zhang H, Huang C, Yang Z, Ranasinghe A, Everlof G, Raghavan N, Tye CK, Wee S, Hunt JT, Vite G, Westhouse R, Lee FY. Discovery and Preclinical Pharmacology of an Oral Bromodomain and Extra-Terminal (BET) Inhibitor Using Scaffold-Hopping and Structure-Guided Drug Design. J Med Chem. 2021 Oct 14;64(19):14247-14265. doi: 10.1021/acs.jmedchem.1c00625. Epub 2021 Sep 20. PMID: 34543572. 7: Pearson AD, DuBois SG, Buenger V, Kieran M, Stegmaier K, Bandopadhayay P, Bennett K, Bourdeaut F, Brown PA, Chesler L, Clymer J, Fox E, French CA, Germovsek E, Giles FJ, Bender JG, Hattersley MM, Ludwinski D, Luptakova K, Maris J, McDonough J, Nikolova Z, Smith M, Tsiatis AC, Vibhakar R, Weiner S, Yi JS, Zheng F, Vassal G. Bromodomain and extra-terminal inhibitors-A consensus prioritisation after the Paediatric Strategy Forum for medicinal product development of epigenetic modifiers in children-ACCELERATE. Eur J Cancer. 2021 Mar;146:115-124. doi: 10.1016/j.ejca.2021.01.018. Epub 2021 Feb 16. PMID: 33601323. 8: Sun Y, Han J, Wang Z, Li X, Sun Y, Hu Z. Safety and Efficacy of Bromodomain and Extra-Terminal Inhibitors for the Treatment of Hematological Malignancies and Solid Tumors: A Systematic Study of Clinical Trials. Front Pharmacol. 2021 Jan 26;11:621093. doi: 10.3389/fphar.2020.621093. PMID: 33574760; PMCID: PMC7870522. 9: Yin M, Guo Y, Hu R, Cai WL, Li Y, Pei S, Sun H, Peng C, Li J, Ye R, Yang Q, Wang N, Tao Y, Chen X, Yan Q. Potent BRD4 inhibitor suppresses cancer cell- macrophage interaction. Nat Commun. 2020 Apr 14;11(1):1833. doi: 10.1038/s41467-020-15290-0. PMID: 32286255; PMCID: PMC7156724.