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]
Referencesedit
^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.
^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.
^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.
^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.
^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.
External linksedit
Numerous references and links to current and past clinical trials and studies of fenretinide can be found at the Journal of Clinical Oncology website
April 10, 2024
fenretinide, hydroxyphenyl, retinamide, synthetic, retinoid, derivative, retinoids, substances, related, vitamin, been, investigated, potential, treatment, cancer, well, treatment, cystic, fibrosis, rheumatoid, arthritis, acne, psoriasis, been, found, also, sl. 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 NamesIUPAC name N 4 Hydroxyphenyl retinamideSystematic 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 tetraenamideIdentifiersCAS Number 65646 68 6 Y3D model JSmol Interactive imageChEMBL ChEMBL7301 YChemSpider 4450416 YDrugBank DB05076 YECHA InfoCard 100 164 069KEGG D04162 YMeSH FenretinidePubChem CID 5288209UNII 187EJ7QEXL YCompTox Dashboard EPA DTXSID2032005InChI 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 YKey AKJHMTWEGVYYSE FXILSDISSA N YInChI 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 FXILSDISBUSMILES O C Nc1ccc O cc1 C C C C C C C C C2 C CCCC2 C C C C CPropertiesChemical formula C 26H 33N O 2Molar mass 391 546 g molExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N 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 citation needed References edit 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 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 amp Visual Science 46 12 4393 401 doi 10 1167 iovs 05 0820 PMID 16303925 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 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 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 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 External links editNumerous references and links to current and past clinical trials and studies of fenretinide can be found at the Journal of Clinical Oncology website Retrieved from https en wikipedia org w index php title Fenretinide amp oldid 1188071054, wikipedia, wiki, book, books, library,
