Fenretinide


Catalog No. size PriceQuantity
M6673-2 2mg solid $75
M6673-10 10mg solid $328

Description

Cas:65646-68-6

Product Information

Fenretinide is an orally-active synthetic phenylretinamide analogue of retinol (vitamin A) with potential antineoplastic and chemopreventive activities. Fenretinide binds to and activates retinoic acid receptors (RARs), thereby inducing cell differentiation and apoptosis in some tumor cell types. This agent also inhibits tumor growth by modulating angiogenesis-associated growth factors and their receptors and exhibits retinoid receptor-independent apoptotic properties.

 

Chemical Formula: C26H33NO2

 

Exact Mass: 391.25113

 

Molecular Weight: 391.54572

 

Elemental Analysis: C, 79.76; H, 8.50; N, 3.58; O, 8.17

 

Synonym: 

 

4-HP

McNR-1967

McNR1967

McNR 1967

HPR

Fenretinide

 

Chemical Name:  

(2E,4E,6E,8E)-N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenamide

 

InChi Key:

AKJHMTWEGVYYSE-FXILSDISSA-N

 

InChi Code:   InChI=1S/C26H33NO2/c1-19(11-16-24-21(3)10-7-17-26(24,4)5)8-6-9-20(2)18-25(29)27-22-12-14-23(28)15-13-22/h6,8-9,11-16,18,28H,7,10,17H2,1-5H3,(H,27,29)/b9-6+,16-11+,19-8+,20-18+

 

Smiles Code:

O=C(NC1=CC=C(O)C=C1)/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)CCCC2(C)C

 

 

Technical Data:

 

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: >5 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

 

In Vitro

Fenretinide (4-HPR) exerts not just acute but also long term antitumor activity in selected T-ALL cell lines. Fenretinide inhibits DES activity in CCRF-CEM leukemia cells in a dose and time dependent manner, leading to a concomitant increase of the endogenous cellular dhCer content. Fenretinide (3 μM)-induced dhCer accumulation in both CCRF-CEM and Jurkat cells. Ceramide inhibition with fenretinide protects insulin signaling. Fenretinide prevents lipid-induced reductions in insulin-stimulated glucose uptake. Fenretinide inhibits OVCAR-5 cell proliferation and viability at concentrations higher than 1 microM, with 70-90% growth inhibition at 10 microM. Fenretinide (1 microM) significantly inhibits OVCAR-5 invasion after 3 days preincubation. Endothelial cells treated with 1 microM 4-HPR fails to form tubes, but forms small cellular aggregates.

 

In Vivo

Fenretinide (4-HPR) (10 mg/kg, i.p.) selectively inhibits ceramide accumulation HFD-fed male C57Bl/6 mice. Fenretinide treatment improves glucose tolerance and insulin sensitivity as determined by both glucose and insulin tolerance tests. Addition of 25 mg/kg ketoconazole to Fenretinide in NOD/SCID mice increased 4-HPR plasma levels.

 

 

References

 

  1. Armstrong JL, Martin S, Illingworth NA, Jamieson D, Neilson A, Lovat PE, Redfern CP, Veal GJ. The impact of retinoic acid treatment on the sensitivity of neuroblastoma cells to fenretinide. Oncol Rep. 2012 Jan;27(1):293-8. doi: 10.3892/or.2011.1479. Epub 2011 Sep 29. PubMed PMID: 21964808.

 

  1. Fang H, Harned TM, Kalous O, Maldonado V, Declerck YA, Reynolds CP. Synergistic Activity of Fenretinide and the Bcl-2 Family Protein Inhibitor ABT-737 against Human Neuroblastoma. Clin Cancer Res. 2011 Nov 8. [Epub ahead of print] PubMed PMID: 21933888.

 

  1. Villablanca JG, London WB, Naranjo A, McGrady P, Ames MM, Reid JM, McGovern RM, Buhrow SA, Jackson H, Stranzinger E, Kitchen BJ, Sondel PM, Parisi MT, Shulkin B, Yanik GA, Cohn SL, Reynolds CP. Phase II Study of Oral Capsular 4-Hydroxyphenylretinamide (4-HPR/Fenretinide) in Pediatric Patients with Refractory or Recurrent Neuroblastoma: A Report from the Children's Oncology Group. Clin Cancer Res. 2011 Nov 1;17(21):6858-6866. Epub 2011 Sep 9. PubMed PMID: 21908574; PubMed Central PMCID: PMC3207022.

 

  1. Carr AJ, Vugler AA, Yu L, Semo M, Coffey P, Moss SE, Greenwood J. The expression of retinal cell markers in human retinal pigment epithelial cells and their augmentation by the synthetic retinoid fenretinide. Mol Vis. 2011;17:1701-15. Epub 2011 Jun 25. PubMed PMID: 21738400; PubMed Central PMCID: PMC3130725.

 

  1. Desai KG, Mallery SR, Holpuch AS, Schwendeman SP. Development and in vitro-in vivo evaluation of fenretinide-loaded oral mucoadhesive patches for site-specific chemoprevention of oral cancer. Pharm Res. 2011 Oct;28(10):2599-609. Epub 2011 Jun 15. PubMed PMID: 21674264; PubMed Central PMCID: PMC3171589.

 

Products are for research use only. Not for human use.

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