Chemistry:Fenretinide
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| IUPAC name
N-(4-Hydroxyphenyl)retinamide
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| Systematic IUPAC 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 | |
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3D model (JSmol)
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| KEGG | |
| MeSH | Fenretinide |
PubChem CID
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| Properties | |
| C26H33NO2 | |
| Molar mass | 391.546 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
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| Infobox references | |
Fenretinide (N-(4-hydroxyphenyl)retinamide; 4-HPR) (INN) is a synthetic retinoid derivative. 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,[1] 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.[2]
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.[3] Fenretinide accumulates preferentially in fatty tissue such as the breast, which may contribute to the effectiveness of fenretinide against breast cancer.[4][5] Phase III clinical trial data has suggested that fenretinide reduces breast cancer relapse in pre-menopausal women.[6] 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.[citation needed]
References
- ↑ "Fenretinide corrects newly found ceramide deficiency in cystic fibrosis". American Journal of Respiratory Cell and Molecular Biology 38 (1): 47–56. January 2008. doi:10.1165/rcmb.2007-0036OC. PMID 17656682.
- ↑ "Reductions in serum vitamin A arrest accumulation of toxic retinal fluorophores: a potential therapy for treatment of lipofuscin-based retinal diseases". Investigative Ophthalmology & Visual Science 46 (12): 4393–401. December 2005. doi:10.1167/iovs.05-0820. PMID 16303925.
- ↑ "Mechanism of fenretinide (4-HPR)-induced cell death". Apoptosis 6 (5): 377–88. October 2001. doi:10.1023/A:1011342220621. PMID 11483862.
- ↑ "Five-year administration of fenretinide: pharmacokinetics and effects on plasma retinol concentrations". Journal of Clinical Oncology 11 (10): 2036–42. October 1993. doi:10.1200/jco.1993.11.10.2036. PMID 8410127.
- ↑ "Breast tissue accumulation of retinamides in a randomized short-term study of fenretinide". Clinical Cancer Research 9 (7): 2400–5. July 2003. PMID 12855611.
- ↑ "Fifteen-year results of a randomized phase III trial of fenretinide to prevent second breast cancer". Annals of Oncology 17 (7): 1065–71. July 2006. doi:10.1093/annonc/mdl047. PMID 16675486.
External links
- Numerous references and links to current and past clinical trials and studies of fenretinide can be found at the Journal of Clinical Oncology website
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