Fenretinide
| Fenretinide |
|
15-[(4-hydroxyphenyl)amino]retinal
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| Identifiers |
| CAS number |
65646-68-6 Y |
| PubChem |
5288209 |
| ChemSpider |
4450416 Y |
| DrugBank |
DB05076 |
| KEGG |
D04162 Y |
| MeSH |
Fenretinide |
| ChEMBL |
CHEMBL7301 Y |
| Jmol-3D images |
Image 1 |
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O=C(Nc1ccc(O)cc1)\C=C(\C=C\C=C(\C=C\C2=C(\CCCC2(C)C)C)C)C
|
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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+ Y
Key: AKJHMTWEGVYYSE-FXILSDISSA-N Y
InChI=1/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+
Key: AKJHMTWEGVYYSE-FXILSDISBU
|
| Properties |
| Molecular formula |
C26H33NO2 |
| Molar mass |
391.55 g mol−1 |
Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
| Infobox references |
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,[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.
References
- ^ Guilbault C, De Sanctis JB, Wojewodka G, Saeed Z, Lachance C, Skinner TA, Vilela RM, Kubow S, Lands LC, Hajduch M, Matouk E, Radzioch D. (2008). "Fenretinide Corrects Newly Found Ceramide Deficiency in Cystic Fibrosis". Am J Respir Cell Mol Biol 38 (1): 47–56. doi:10.1165/rcmb.2007-0036OC. PMID 17656682.
- ^ Radu, Roxana A., Yun Han, Tam V. Bui, Steven Nusinowitz, Dean Bok, Jay Lichter, Ken Widder, Gabriel H. Travis, and Nathan L. Mata. (2005). "Reductions in Serum Vitamin A Arrest Accumulation of Toxic Retinal Fluorophores: A Potential Therapy for Treatment of Lipofuscin-Based Retinal Diseases.". IOVS 46: 4393–401.
- ^ Wu J, DiPietrantonio A, Hsieh T (2001). "Mechanism of fenretinide (4-HPR)-induced cell death". Apoptosis 6 (5): 377–88. doi:10.1023/A:1011342220621. PMID 11483862.
- ^ Formelli, Franca; Monica Clerici, Tiziana Campa, MAria Gaetana Di Mauro, Andrea Magni, Gustavo Mascotti, Daniele Moglia, Giuseppe De Palo, Alberto Costa, Umberto Veronesi (October 1993). "Five-Year Administration of Fenretinide: Pharmacokinetics and Effects on Plasma Retinol Concentrations". Journal of Clinical Oncology 11 (10): 2036–2042. PMID 8410127.
- ^ Sabichi, Anita; Manual Modiano, J. Jack Lee, Yei-Mei Peng, Ming-Jing Xu, Hugo Vallar, William Dalton, Scott Lippman (July 2003). "Breast Tissue Accumulation of Retinamides in a Randomized Short-term Study of Fenretinide". Clinical Cancer Research 9 (7): 2400–2405. PMID 12855611.
- ^ Veronesi, U.; L. Mariani, A. Decensi, F. Formelli, T. Camerini, R. Miceli, M. G. Di Mauro, A. Costa, E. Marubini, M. B. Sporn, G. De Palo (NaN undefined NaN). "Fifteen-year results of a randomized phase III trial of fenretinide to prevent second breast cancer". Annals of Oncology 17 (7): 1065–1071. doi:10.1093/annonc/mdl047. PMID 16675486.
External links