Fenretinide
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.
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.
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.
| Chemical | |
|---|---|
| CAS Num | 65646-68-6 |
| Chemical Formula | C26H33NO2 |
| Molecular Weight | 391.54572 |
| 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 |
| Exact Mass | 391.25113 |
| Elemental Analysis | C, 79.76; H, 8.50; N, 3.58; O, 8.17 |
| Synonym | 4-HPR; McNR-1967; HPR; Fenretinide |
| Solubility | Soluble in DMSO, not in water |
| 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 |
| Biological | |
| Targets and Effects | retinoic acid receptor (RAR) |
| Pathways | Apoptosis |
| Physical | |
| 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). |
| Shelf Life | >5 years if stored properly |
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