Efatutazone Free Base | CAS# 223132-37-4 (free base) | Antineoplastic Agent

MedKoo Cat#: 414004 | Name: Efatutazone Free Base

Description:

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

Efatutazone Free Base is a high-affinity PPARgamma agonist with antineoplastic activity.

Chemical Structure

Efatutazone Free Base

CAS#223132-37-4 (free base)

Theoretical Analysis

MedKoo Cat#: 414004

Name: Efatutazone Free Base

CAS#: 223132-37-4 (free base)

Chemical Formula: C27H26N4O4S

Exact Mass: 502.1675

Molecular Weight: 502.58

Elemental Analysis: C, 64.53; H, 5.21; N, 11.15; O, 12.73; S, 6.38

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 #

223132-37-4 (free base) 223132-38-5 (HCl)

Synonym

Efatutazone Free Base; Inolitazone

IUPAC/Chemical Name

5-(4-((6-(4-amino-3,5-dimethylphenoxy)-1-methyl-1H-benzo[d]imidazol-2-yl)methoxy)benzyl)thiazolidine-2,4-dione

InChi Key

JCYNMRJCUYVDBC-UHFFFAOYSA-N

InChi Code

InChI=1S/C27H26N4O4S/c1-15-10-20(11-16(2)25(15)28)35-19-8-9-21-22(13-19)31(3)24(29-21)14-34-18-6-4-17(5-7-18)12-23-26(32)30-27(33)36-23/h4-11,13,23H,12,14,28H2,1-3H3,(H,30,32,33)

SMILES Code

Cc1c(N)c(C)cc(Oc(cc2)cc3c2nc(COc4ccc(CC5SC(NC5=O)=O)cc4)n3C)c1

Appearance

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).

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 502.58 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.

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: Ni J, Zhou LL, Ding L, Zhang XQ, Zhao X, Li H, Cao H, Liu S, Wang Z, Ma R, Wu J, Feng J. Efatutazone and T0901317 exert synergistically therapeutic effects in acquired gefitinib-resistant lung adenocarcinoma cells. Cancer Med. 2018 May;7(5):1955-1966. doi: 10.1002/cam4.1440. Epub 2018 Mar 23. PMID: 29573196; PMCID: PMC5943475. 2: Alothman SJ, Wang W, Chao S, Kallakury BV, Díaz-Cruz ES, Furth PA. Differential efatutazone's impact on mammary neoplasia dependent upon Brca1 dose. Endocr Relat Cancer. 2018 Dec 1;25(12):L53-L57. doi: 10.1530/ERC-18-0299. PMID: 30400020; PMCID: PMC6944742. 3: Ferrari SM, Elia G, Ragusa F, Ruffilli I, La Motta C, Paparo SR, Patrizio A, Vita R, Benvenga S, Materazzi G, Fallahi P, Antonelli A. Novel treatments for anaplastic thyroid carcinoma. Gland Surg. 2020 Jan;9(Suppl 1):S28-S42. doi: 10.21037/gs.2019.10.18. PMID: 32055496; PMCID: PMC6995904. 4: Ory V, Kietzman WB, Boeckelman J, Kallakury BV, Wellstein A, Furth PA, Riegel AT. The PPARγ agonist efatutazone delays invasive progression and induces differentiation of ductal carcinoma in situ. Breast Cancer Res Treat. 2018 May;169(1):47-57. doi: 10.1007/s10549-017-4649-y. Epub 2018 Jan 19. PMID: 29350308; PMCID: PMC5884724. 5: Molinaro E, Romei C, Biagini A, Sabini E, Agate L, Mazzeo S, Materazzi G, Sellari-Franceschini S, Ribechini A, Torregrossa L, Basolo F, Vitti P, Elisei R. Anaplastic thyroid carcinoma: from clinicopathology to genetics and advanced therapies. Nat Rev Endocrinol. 2017 Nov;13(11):644-660. doi: 10.1038/nrendo.2017.76. Epub 2017 Jul 14. PMID: 28707679. 6: De Leo S, Trevisan M, Fugazzola L. Recent advances in the management of anaplastic thyroid cancer. Thyroid Res. 2020 Nov 24;13(1):17. doi: 10.1186/s13044-020-00091-w. PMID: 33292371; PMCID: PMC7684758. 7: Ni J, Zhou LL, Ding L, Zhao X, Cao H, Fan F, Li H, Lou R, Du Y, Dong S, Liu S, Wang Z, Ma R, Wu J, Feng J. PPARγ agonist efatutazone and gefitinib synergistically inhibit the proliferation of EGFR-TKI-resistant lung adenocarcinoma cells via the PPARγ/PTEN/Akt pathway. Exp Cell Res. 2017 Dec 15;361(2):246-256. doi: 10.1016/j.yexcr.2017.10.024. Epub 2017 Oct 26. PMID: 29080795. 8: Smallridge RC, Copland JA, Brose MS, Wadsworth JT, Houvras Y, Menefee ME, Bible KC, Shah MH, Gramza AW, Klopper JP, Marlow LA, Heckman MG, Von Roemeling R. Efatutazone, an oral PPAR-γ agonist, in combination with paclitaxel in anaplastic thyroid cancer: results of a multicenter phase 1 trial. J Clin Endocrinol Metab. 2013 Jun;98(6):2392-400. doi: 10.1210/jc.2013-1106. Epub 2013 Apr 15. PMID: 23589525; PMCID: PMC3667260. 9: Murakami H, Ono A, Takahashi T, Onozawa Y, Tsushima T, Yamazaki K, Jikoh T, Boku N, Yamamoto N. Phase I study of Efatutazone, an oral PPARγ agonist, in patients with metastatic solid tumors. Anticancer Res. 2014 Sep;34(9):5133-41. PMID: 25202104. 10: Nakles RE, Kallakury BV, Furth PA. The PPARγ agonist efatutazone increases the spectrum of well-differentiated mammary cancer subtypes initiated by loss of full-length BRCA1 in association with TP53 haploinsufficiency. Am J Pathol. 2013 Jun;182(6):1976-85. doi: 10.1016/j.ajpath.2013.02.006. Epub 2013 May 8. PMID: 23664366; PMCID: PMC3668033.