関: 4-HPR、4-hydroxyphenylretinamide

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/06/29 19:42:19」(JST)

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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

^ 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. doi:10.1167/iovs.05-0820.
^ 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 (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.

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

UpToDate Contents

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1. Chemoprevention of urothelial carcinoma of the bladder
2. 神経芽腫の治療および予後 treatment and prognosis of neuroblastoma
3. 転移性ホルモン受容体陽性乳癌に対する治療アプローチ：内分泌療法 treatment approach to metastatic hormone receptor positive breast cancer endocrine therapy
4. 前立腺癌における化学的予防策 chemoprevention strategies in prostate cancer
5. 肺癌の化学予防 chemoprevention of lung cancer

English Journal

The bioactive lipid 4-hydroxyphenyl retinamide inhibits flavivirus replication.

Carocci M1, Hinshaw SM2, Rodgers MA1, Villareal VA1, Burri DJ1, Pilankatta R1, Maharaj NP1, Gack MU1, Stavale EJ3, Warfield KL3, Yang PL4.
Antimicrobial agents and chemotherapy.Antimicrob Agents Chemother.2015 Jan;59(1):85-95. doi: 10.1128/AAC.04177-14. Epub 2014 Oct 13.
Dengue virus (DENV), a member of the Flaviviridae family, is a mosquito-borne pathogen and the cause of dengue fever. The increasing prevalence of DENV worldwide heightens the need for an effective vaccine and specific antivirals. Due to the dependence of DENV upon the lipid biosynthetic machinery o
PMID 25313218

Preparation and in vitro evaluation of hydrophilic fenretinide nanoparticles.

Ledet GA1, Graves RA1, Glotser EY1, Mandal TK1, Bostanian LA2.
International journal of pharmaceutics.Int J Pharm.2014 Dec 24. pii: S0378-5173(14)00949-1. doi: 10.1016/j.ijpharm.2014.12.052. [Epub ahead of print]
Fenretinide is an effective anti-cancer drug with high in vitro cytotoxicity and low in vivo systemic toxicity. In clinical trials, fenretinide has shown poor therapeutic efficacy following oral administration - attributed to its low bioavailability and solubility. The long term goal of this project
PMID 25542987

Natural inhibitors of PI3K/AKT signaling in breast cancer: Emphasis on newly-discovered molecular mechanisms of action.

Safdari Y1, Khalili M2, Ebrahimzadeh MA3, Yazdani Y4, Farajnia S5.
Pharmacological research : the official journal of the Italian Pharmacological Society.Pharmacol Res.2014 Dec 19;93C:1-10. doi: 10.1016/j.phrs.2014.12.004. [Epub ahead of print]
Epidermal growth factor receptor (EGFR) plays a critical role in the initiation and progression of a variety of human cancers, including breast cancer. An important signaling pathway downstream of EGFR is the PI3K/AKt pathway, which regulates cellular processes as diverse as cell growth, survival, p
PMID 25533812

Japanese Journal

抗酸化作用をもつ抗癌剤の創製 : Fenretinideの構造活性相関研究 (星薬科大学医薬品化学研究所紀要)

高橋典子
星薬科大学紀要 (54), 105-114, 2012
NAID 40019589517

Fenretinide Ameliorates Insulin Resistance and Fatty Liver in Obese Mice

Koh In-uk,Jun Hye-Seung,Choi Joo Sun [他],Lim Joo Hyun,Kim Won Ho,Yoon Jong Bok,Song Jihyun
Biological and Pharmaceutical Bulletin 35(3), 369-375, 2012
… Fenretinide (FEN), a ligand of retinol binding protein 4 (RBP4), has been suggested as a measure to reduce insulin resistance and its associated disorders such as obesity, and fatty liver by reducing serum RBP4. … We investigated whether there is another possible mechanism by which fenretinide reduces insulin resistance and fatty liver in genetically obese (ob/ob) mice. …
NAID 130001872318

神経芽腫とレチノイド

井上彰子,瀧谷公隆
ビタミン 84(10), 493-495, 2010-10-25
NAID 110007817657

Related Pictures

Fenretinide Specification Fenretinide-d4 Glucuronide Visual cycle [ edit ] filling model of the Fenretinide molecule Skeletal formula of fenretinide File:Tamoxifen Raloxifen nci-vol-2738-300 Fenretinide Cuts The Fenretinide prevents the development of

★リンクテーブル★

リンク元	「4-HPR」「4-hydroxyphenylretinamide」「フェンレチニド」

「4-HPR」

Fenretinide
Names
	IUPAC name 15-[(4-hydroxyphenyl)amino]retinal
Identifiers
CAS Registry Number	65646-68-6
ChEMBL	ChEMBL7301
ChemSpider	4450416
DrugBank	DB05076
	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+ ; Key: AKJHMTWEGVYYSE-FXILSDISSA-N ; 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 ;
Jmol-3D images	Image
KEGG	D04162
MeSH	Fenretinide
PubChem	5288209
	SMILES O=C(Nc1ccc(O)cc1)\C=C(\C=C\C=C(\C=C\C2=C(\CCCC2(C)C)C)C)C ;
UNII	187EJ7QEXL
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).
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	Infobox references