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

MedKoo CAT#: 205430

CAS#: 65646-68-6

Description: 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.


Price and Availability

Size
Price

10mg
USD 150
100mg
USD 750
1g
USD 2450
Size
Price

25mg
USD 250
200mg
USD 1250
2g
USD 3850
Size
Price

50mg
USD 450
500mg
USD 1750
5g
USD 5750

Fenretinide, purity > 98%, is in stock. The same day shipping out after order is received. Note: the estimated shipping out time for order > 4g may be 2 weeks.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 205430
Name: Fenretinide
CAS#: 65646-68-6
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-HPR; McNR-1967; HPR; Fenretinide

IUPAC/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)

Certificate of Analysis:

Safety Data Sheet (MSDS):

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).

Harmonized System Code:
293490


Additional Information

Fenretinide (4-hydroxy(phenyl)retinamide; 4-HPR) (INN) is a synthetic retinoid deriverative. Retinoids are substances related to vitamin A. It has been investigated for potential use in the treatment of cancer, as well as in the treatment of cystic fibrosis,  rheumatoid arthritis, acne, psoriasis, and has been found to also slow the production and accumulation of a toxin that leads to vision loss in Stargardt's patients.
 
In cancer studies, Fenretinide treatment may cause ceramide (a wax-like substance) to build up in tumor cells and is associated with the accumulation of reactive oxygen species (ROS), resulting in cell death through apoptosis and/or necrosis. Fenretinide accumulates preferentially in fatty tissue such as the breast, which may contribute to the effectiveness of fenretinide against breast cancer. Phase III clinical trial data has suggested that fenretinide reduces breast cancer relapse in pre-menopausal women . Common side effects associated with fenretinide treatment include skin dryness and night-blindness, which is reversible upon cessation of treatment. Specific types of cancer under investigation include or have included ovarian, prostate, cervical, lung, renal, bladder, breast, glioma, skin, head and neck carcinoma, Non-Hodgkin's lymphoma, neuroblastoma, and Ewing's sarcoma. (source: http://en.wikipedia.org/wiki/Fenretinide).
  
 
 


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.

2: 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.

3: 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.

4: 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.

5: 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.

6: Campos-Sandoval JA, Redondo C, Kinsella GK, Pal A, Jones G, Eyre GS, Hirst SC, Findlay JB. Fenretinide derivatives act as disrupters of interactions of serum retinol binding protein (sRBP) with transthyretin and the sRBP receptor. J Med Chem. 2011 Jul 14;54(13):4378-87. Epub 2011 Jun 7. PubMed PMID: 21591606.

7: Rahmaniyan M, Curley RW Jr, Obeid LM, Hannun YA, Kraveka JM. Identification of dihydroceramide desaturase as a direct in vitro target for fenretinide. J Biol Chem. 2011 Jul 15;286(28):24754-64. Epub 2011 May 4. PubMed PMID: 21543327; PubMed Central PMCID: PMC3137051.

8: Kummar S, Gutierrez ME, Maurer BJ, Reynolds CP, Kang M, Singh H, Crandon S, Murgo AJ, Doroshow JH. Phase I trial of fenretinide lym-x-sorb oral powder in adults with solid tumors and lymphomas. Anticancer Res. 2011 Mar;31(3):961-6. PubMed PMID: 21498721.

9: Cooper JP, Hwang K, Singh H, Wang D, Reynolds CP, Curley RW Jr, Williams SC, Maurer BJ, Kang MH. Fenretinide metabolism in humans and mice: utilizing pharmacological modulation of its metabolic pathway to increase systemic exposure. Br J Pharmacol. 2011 Jul;163(6):1263-75. doi: 10.1111/j.1476-5381.2011.01310.x. PubMed PMID: 21391977; PubMed Central PMCID: PMC3144539.

10: Yang H, Zhan Q, Wan YJ. Enrichment of Nur77 mediated by retinoic acid receptor β leads to apoptosis of human hepatocellular carcinoma cells induced by fenretinide and histone deacetylase inhibitors. Hepatology. 2011 Mar;53(3):865-74. doi: 10.1002/hep.24101. Epub 2011 Feb 11. PubMed PMID: 21319187; PubMed Central PMCID: PMC3077573.