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MedKoo Cat#: 524980 | Name: Efatutazone hydrochloride

Description:

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

Efatutazone hydrochloride is an oral, high-affinity PPAR-γ agonist with with antineoplastic activity.

Chemical Structure

Efatutazone hydrochloride
Efatutazone hydrochloride
CAS#223132-38-5 (HCl)

Theoretical Analysis

MedKoo Cat#: 524980

Name: Efatutazone hydrochloride

CAS#: 223132-38-5 (HCl)

Chemical Formula: C27H28Cl2N4O4S

Exact Mass:

Molecular Weight: 575.51

Elemental Analysis: C, 56.35; H, 4.90; Cl, 12.32; N, 9.74; O, 11.12; S, 5.57

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 hydrochloride; CS 7017; CS-7017; CS7017 ;RS-5444; RS5444; UNII-76B44WEA8O.
IUPAC/Chemical Name
2,4-Thiazolidinedione, 5-((4-((6-(4-amino-3,5-dimethylphenoxy)-1-methyl-1H-benzimidazol-2-yl)methoxy)phenyl)methyl)-, dihydrochloride
InChi Key
WFIOHOJEIMQCEG-UHFFFAOYSA-N
InChi Code
InChI=1S/C27H26N4O4S.2ClH/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);2*1H
SMILES Code
c1cc(cc2c1nc(n2C)COc1ccc(cc1)CC1SC(=O)NC1=O)Oc1cc(c(c(c1)C)N)C.Cl.Cl
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
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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 575.51 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: Aprile G, Giuliani F, Lutrino SE, Fontanella C, Bonotto M, Rihawi K, Fasola G. Maintenance Therapy in Colorectal Cancer: Moving the Artillery Down While Keeping an Eye on the Enemy. Clin Colorectal Cancer. 2016 Mar;15(1):7-15. doi: 10.1016/j.clcc.2015.08.002. Epub 2015 Aug 22. Review. PubMed PMID: 26421728. 2: Williams R. Discontinued in 2013: oncology drugs. Expert Opin Investig Drugs. 2015 Jan;24(1):95-110. Epub 2014 Oct 14. PubMed PMID: 25315907. 3: 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. PubMed PMID: 25202104. 4: Serizawa M, Murakami H, Watanabe M, Takahashi T, Yamamoto N, Koh Y. Peroxisome proliferator-activated receptor γ agonist efatutazone impairs transforming growth factor β2-induced motility of epidermal growth factor receptor tyrosine kinase inhibitor-resistant lung cancer cells. Cancer Sci. 2014 Jun;105(6):683-9. doi: 10.1111/cas.12411. Epub 2014 May 10. PubMed PMID: 24698130; PubMed Central PMCID: PMC4317891. 5: Dabydeen SA, Furth PA. Genetically engineered ERα-positive breast cancer mouse models. Endocr Relat Cancer. 2014 May 6;21(3):R195-208. doi: 10.1530/ERC-13-0512. Print 2014 Jun. Review. PubMed PMID: 24481326; PubMed Central PMCID: PMC4013173. 6: Komatsu Y, Yoshino T, Yamazaki K, Yuki S, Machida N, Sasaki T, Hyodo I, Yachi Y, Onuma H, Ohtsu A. Phase 1 study of efatutazone, a novel oral peroxisome proliferator-activated receptor gamma agonist, in combination with FOLFIRI as second-line therapy in patients with metastatic colorectal cancer. Invest New Drugs. 2014 Jun;32(3):473-80. doi: 10.1007/s10637-013-0056-3. Epub 2013 Dec 15. PubMed PMID: 24337768; PubMed Central PMCID: PMC4045340. 7: Sawayama H, Ishimoto T, Watanabe M, Yoshida N, Sugihara H, Kurashige J, Hirashima K, Iwatsuki M, Baba Y, Oki E, Morita M, Shiose Y, Baba H. Small molecule agonists of PPAR-γ exert therapeutic effects in esophageal cancer. Cancer Res. 2014 Jan 15;74(2):575-85. doi: 10.1158/0008-5472.CAN-13-1836. Epub 2013 Nov 22. PubMed PMID: 24272485. 8: 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. PubMed PMID: 23664366; PubMed Central PMCID: PMC3668033. 9: Dong JT. Anticancer activities of PPARγ in breast cancer are context-dependent. Am J Pathol. 2013 Jun;182(6):1972-5. doi: 10.1016/j.ajpath.2013.03.005. Epub 2013 Apr 22. PubMed PMID: 23619477. 10: 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. PubMed PMID: 23589525; PubMed Central PMCID: PMC3667260. 11: Pishvaian MJ, Marshall JL, Wagner AJ, Hwang JJ, Malik S, Cotarla I, Deeken JF, He AR, Daniel H, Halim AB, Zahir H, Copigneaux C, Liu K, Beckman RA, Demetri GD. A phase 1 study of efatutazone, an oral peroxisome proliferator-activated receptor gamma agonist, administered to patients with advanced malignancies. Cancer. 2012 Nov 1;118(21):5403-13. doi: 10.1002/cncr.27526. Epub 2012 May 8. PubMed PMID: 22570147; PubMed Central PMCID: PMC3726261. 12: Marlow LA, Reynolds LA, Cleland AS, Cooper SJ, Gumz ML, Kurakata S, Fujiwara K, Zhang Y, Sebo T, Grant C, McIver B, Wadsworth JT, Radisky DC, Smallridge RC, Copland JA. Reactivation of suppressed RhoB is a critical step for the inhibition of anaplastic thyroid cancer growth. Cancer Res. 2009 Feb 15;69(4):1536-44. doi: 10.1158/0008-5472.CAN-08-3718. Epub 2009 Feb 10. PubMed PMID: 19208833; PubMed Central PMCID: PMC2644344. 13: Su W, Necela BM, Fujiwara K, Kurakata S, Murray NR, Fields AP, Thompson EA. The high affinity peroxisome proliferator-activated receptor-gamma agonist RS5444 inhibits both initiation and progression of colon tumors in azoxymethane-treated mice. Int J Cancer. 2008 Sep 1;123(5):991-7. doi: 10.1002/ijc.23640. PubMed PMID: 18546290; PubMed Central PMCID: PMC3902358. 14: Shimazaki N, Togashi N, Hanai M, Isoyama T, Wada K, Fujita T, Fujiwara K, Kurakata S. Anti-tumour activity of CS-7017, a selective peroxisome proliferator-activated receptor gamma agonist of thiazolidinedione class, in human tumour xenografts and a syngeneic tumour implant model. Eur J Cancer. 2008 Aug;44(12):1734-43. doi: 10.1016/j.ejca.2008.04.016. Epub 2008 May 27. PubMed PMID: 18511262. 15: Su W, Bush CR, Necela BM, Calcagno SR, Murray NR, Fields AP, Thompson EA. Differential expression, distribution, and function of PPAR-gamma in the proximal and distal colon. Physiol Genomics. 2007 Aug 20;30(3):342-53. Epub 2007 May 22. PubMed PMID: 17519361. 16: Chen L, Bush CR, Necela BM, Su W, Yanagisawa M, Anastasiadis PZ, Fields AP, Thompson EA. RS5444, a novel PPARgamma agonist, regulates aspects of the differentiated phenotype in nontransformed intestinal epithelial cells. Mol Cell Endocrinol. 2006 Jun 7;251(1-2):17-32. Epub 2006 Mar 29. PubMed PMID: 16574311. 17: Copland JA, Marlow LA, Kurakata S, Fujiwara K, Wong AK, Kreinest PA, Williams SF, Haugen BR, Klopper JP, Smallridge RC. Novel high-affinity PPARgamma agonist alone and in combination with paclitaxel inhibits human anaplastic thyroid carcinoma tumor growth via p21WAF1/CIP1. Oncogene. 2006 Apr 13;25(16):2304-17. PubMed PMID: 16331265.