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

MedKoo CAT#: 202041

CAS#: 220619-73-8

Description: IRX4204, also know as NRX-4204, NRX-194204 and AGN-194204, is an orally bioavailable synthetic retinoid X receptor (RXR) agonist with potential antineoplastic and anti-inflammatory activities. Rexinoid NRX 194204 selectively binds to and activates RXRs. Because RXRs can form heterodimers with several nuclear receptors (NRs), RXR activation by this agent may result in a broad range of gene expression depending on the effector DNA response elements activated. Rexinoid NRX 194204 may inhibit the tumor-necrosis factor (TNF)-mediated release of nitric oxide (NO) and interleukin 6 (IL6) and may inhibit tumor cell proliferation. This agent appears to be less toxic than RAR-selective ligands.

Chemical Structure

CAS# 220619-73-8

Theoretical Analysis

MedKoo Cat#: 202041
Name: IRX4204
CAS#: 220619-73-8
Chemical Formula: C24H32O2
Exact Mass: 352.24023
Molecular Weight: 352.51
Elemental Analysis: C, 81.77; H, 9.15; O, 9.08

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Synonym: IRX4204; IRX-4204; IRX 4204; NRX4204; NRX-4204; NRX 4204; NRX194204; NRX 194204; NRX-194204; AGN194204; AGN 194204; AGN-194204; VTP 194204; VTP194204; VTP-194204.

IUPAC/Chemical Name: (2E,4E)-3-methyl-5-((1S,2S)-2-methyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)cyclopropyl)penta-2,4-dienoic acid


InChi Code: InChI=1S/C24H32O2/c1-16(13-21(25)26)7-8-18-15-24(18,6)17-9-10-19-20(14-17)23(4,5)12-11-22(19,2)3/h7-10,13-14,18H,11-12,15H2,1-6H3,(H,25,26)/b8-7+,16-13+/t18-,24-/m1/s1

SMILES Code: O=C(O)/C=C(C)/C=C/[C@H]1[C@](C2=CC=C3C(C)(C)CCC(C)(C)C3=C2)(C)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: 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

Preparing Stock Solutions

The following data is based on the product molecular weight 352.51 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

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1: Han JS, Crowe DL. Steroid receptor coactivator 1 deficiency increases MMTV-neu mediated tumor latency and differentiation specific gene expression, decreases metastasis, and inhibits response to PPAR ligands. BMC Cancer. 2010 Nov 16;10:629. doi: 10.1186/1471-2407-10-629. PubMed PMID: 21080969; PubMed Central PMCID: PMC2999618.

2: Liby K, Risingsong R, Royce DB, Williams CR, Ma T, Yore MM, Sporn MB. Triterpenoids CDDO-methyl ester or CDDO-ethyl amide and rexinoids LG100268 or NRX194204 for prevention and treatment of lung cancer in mice. Cancer Prev Res (Phila). 2009 Dec;2(12):1050-8. doi: 10.1158/1940-6207.CAPR-09-0085. Epub 2009 Dec 1. PubMed PMID: 19952361; PubMed Central PMCID: PMC2818234.

3: Liby K, Royce DB, Risingsong R, Williams CR, Wood MD, Chandraratna RA, Sporn MB. A new rexinoid, NRX194204, prevents carcinogenesis in both the lung and mammary gland. Clin Cancer Res. 2007 Oct 15;13(20):6237-43. PubMed PMID: 17947492.

4: Rasooly R, Schuster GU, Gregg JP, Xiao JH, Chandraratna RA, Stephensen CB. Retinoid x receptor agonists increase bcl2a1 expression and decrease apoptosis of naive T lymphocytes. J Immunol. 2005 Dec 15;175(12):7916-29. PubMed PMID: 16339527.

5: Li X, Hansen PA, Xi L, Chandraratna RA, Burant CF. Distinct mechanisms of glucose lowering by specific agonists for peroxisomal proliferator activated receptor gamma and retinoic acid X receptors. J Biol Chem. 2005 Nov 18;280(46):38317-27. Epub 2005 Sep 22. PubMed PMID: 16179348.

6: Crowe DL, Chandraratna RA. A retinoid X receptor (RXR)-selective retinoid reveals that RXR-alpha is potentially a therapeutic target in breast cancer cell lines, and that it potentiates antiproliferative and apoptotic responses to peroxisome proliferator-activated receptor ligands. Breast Cancer Res. 2004;6(5):R546-55. Epub 2004 Jul 23. PubMed PMID: 15318936; PubMed Central PMCID: PMC549174.

7: Ikezoe T, Tanosaki S, Krug U, Liu B, Cohen P, Taguchi H, Koeffler HP. Insulin-like growth factor binding protein-3 antagonizes the effects of retinoids in myeloid leukemia cells. Blood. 2004 Jul 1;104(1):237-42. Epub 2004 Mar 16. PubMed PMID: 15026318.

8: Balasubramanian S, Chandraratna RA, Eckert RL. Suppression of human pancreatic cancer cell proliferation by AGN194204, an RXR-selective retinoid. Carcinogenesis. 2004 Aug;25(8):1377-85. Epub 2004 Feb 19. PubMed PMID: 14976133.

9: Hellemans K, Verbuyst P, Quartier E, Schuit F, Rombouts K, Chandraratna RA, Schuppan D, Geerts A. Differential modulation of rat hepatic stellate phenotype by natural and synthetic retinoids. Hepatology. 2004 Jan;39(1):97-108. PubMed PMID: 14752828.

10: Schaier M, Liebler S, Schade K, Shimizu F, Kawachi H, Grone HJ, Chandraratna R, Ritz E, Wagner J. Retinoic acid receptor alpha and retinoid X receptor specific agonists reduce renal injury in established chronic glomerulonephritis of the rat. J Mol Med (Berl). 2004 Feb;82(2):116-25. Epub 2004 Jan 8. PubMed PMID: 14712350.

11: Macchia PE, Jiang P, Yuan YD, Chandarardna RA, Weiss RE, Chassande O, Samarut J, Refetoff S, Burant CF. RXR receptor agonist suppression of thyroid function: central effects in the absence of thyroid hormone receptor. Am J Physiol Endocrinol Metab. 2002 Aug;283(2):E326-31. PubMed PMID: 12110538.

12: Stephensen CB, Rasooly R, Jiang X, Ceddia MA, Weaver CT, Chandraratna RA, Bucy RP. Vitamin A enhances in vitro Th2 development via retinoid X receptor pathway. J Immunol. 2002 May 1;168(9):4495-503. PubMed PMID: 11970994.

13: McArthur GA, Foley KP, Fero ML, Walkley CR, Deans AJ, Roberts JM, Eisenman RN. MAD1 and p27(KIP1) cooperate to promote terminal differentiation of granulocytes and to inhibit Myc expression and cyclin E-CDK2 activity. Mol Cell Biol. 2002 May;22(9):3014-23. PubMed PMID: 11940659; PubMed Central PMCID: PMC133749.

14: Standeven AM, Thacher SM, Yuan YD, Escobar M, Vuligonda V, Beard RL, Chandraratna RA. Retinoid X receptor agonist elevation of serum triglycerides in rats by potentiation of retinoic acid receptor agonist induction or by action as single agents. Biochem Pharmacol. 2001 Dec 1;62(11):1501-9. PubMed PMID: 11728386.

15: Alsop D, Brown S, Van Der Kraak G. Development of a retinoic acid receptor-binding assay with rainbow trout tissue: characterization of retinoic acid binding, receptor tissue distribution, and developmental changes. Gen Comp Endocrinol. 2001 Sep;123(3):254-67. PubMed PMID: 11589627.

16: Vuligonda V, Thacher SM, Chandraratna RA. Enantioselective syntheses of potent retinoid X receptor ligands: differential biological activities of individual antipodes. J Med Chem. 2001 Jul 5;44(14):2298-303. PubMed PMID: 11428923.

17: Samuel W, Kutty RK, Nagineni S, Gordon JS, Prouty SM, Chandraratna RA, Wiggert B. Regulation of stearoyl coenzyme A desaturase expression in human retinal pigment epithelial cells by retinoic acid. J Biol Chem. 2001 Aug 3;276(31):28744-50. Epub 2001 Jun 7. PubMed PMID: 11397803.

Additional Information

NRX-4204 is a rexinoid agonist that is targeted for development in non-small cell lung carcinoma and breast cancer and a RAR agonist for the treatment of acute leukemia.