Efatutazone hydrochloride

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

MedKoo CAT#: 524980

CAS#: 223132-38-5 (HCl)

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


Chemical Structure

img
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: 0.00
Molecular Weight: 575.510
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 not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

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:

Biological target:
In vitro activity:
In vivo activity:

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

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.