Fenretinide

Fenretinide
Skeletal formula of fenretinide
Space-filling model of the Fenretinide molecule
Names
IUPAC name
15-[(4-hydroxyphenyl)amino]retinal
Identifiers
65646-68-6 YesY
3D model (Jmol) Interactive image
ChEMBL ChEMBL7301 YesY
ChemSpider 4450416 YesY
DrugBank DB05076 YesY
ECHA InfoCard 100.164.069
KEGG D04162 YesY
MeSH Fenretinide
PubChem 5288209
UNII 187EJ7QEXL YesY
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).
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Infobox references

Fenretinide (4-hydroxy(phenyl)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.

References

  1. ↑ 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.
  2. ↑ Radu RA, Han Y, Bui TV, Nusinowitz S, Bok D, Lichter J, Widder K, Travis GH, Mata NL (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. doi:10.1167/iovs.05-0820.
  3. ↑ 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.
  4. ↑ 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.
  5. ↑ Sabichi AL, Modiano MR, Lee JJ, Peng YM, Xu MJ, Villar H, Dalton WS, Lippman SM (July 2003). "Breast Tissue Accumulation of Retinamides in a Randomized Short-term Study of Fenretinide". Clinical Cancer Research. 9 (7): 2400–2405. PMID 12855611.
  6. ↑ Veronesi U, Mariani L, Decensi A, Formelli F, Camerini T, Miceli R, Di Mauro MG, Costa A, Marubini E, Sporn MB, De Palo G (May 2006). "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.
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