Fenretinide

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]

Fenretinide
Names
Preferred 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
Other names
N-(4-Hydroxyphenyl)retinamide
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.164.069
KEGG
MeSH Fenretinide
PubChem CID
UNII
InChI
  • 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
SMILES
  • O=C(Nc1ccc(O)cc1)\C=C(\C=C\C=C(\C=C\C2=C(\CCCC2(C)C)C)C)C
Properties
Chemical formula
 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).
Y verify (what is YN ?)
Infobox references

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 (January 2008). "Fenretinide corrects newly found ceramide deficiency in cystic fibrosis". American Journal of Respiratory Cell and Molecular Biology. 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 (December 2005). "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. doi:10.1167/iovs.05-0820. PMID 16303925.
  3. Wu JM, DiPietrantonio AM, Hsieh TC (October 2001). "Mechanism of fenretinide (4-HPR)-induced cell death". Apoptosis. 6 (5): 377–88. doi:10.1023/A:1011342220621. PMID 11483862. S2CID 22654270.
  4. Formelli F, Clerici M, Campa T, Di Mauro MG, Magni A, Mascotti G, Moglia D, De Palo G, Costa A, Veronesi U (October 1993). "Five-year administration of fenretinide: pharmacokinetics and effects on plasma retinol concentrations". Journal of Clinical Oncology. 11 (10): 2036–42. doi:10.1200/jco.1993.11.10.2036. 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): 2400–5. 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 (July 2006). "Fifteen-year results of a randomized phase III trial of fenretinide to prevent second breast cancer". Annals of Oncology. 17 (7): 1065–71. doi:10.1093/annonc/mdl047. PMID 16675486.
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