Fenretinide (BioDeep_00000600019)
代谢物信息卡片
4-Hydroxyphenylretinamide
化学式: C26H33NO2 (391.25111580000004)
中文名称: 全反式-N-(4-羟苯基)维甲酸
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC(=O)NC2=CC=C(C=C2)O)C)C
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+
描述信息
C274 - Antineoplastic Agent > C2122 - Cell Differentiating Agent > C1934 - Differentiation Inducer
C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C804 - Retinoic Acid Agent
C308 - Immunotherapeutic Agent > C129820 - Antineoplastic Immunomodulating Agent
D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids
D020011 - Protective Agents > D016588 - Anticarcinogenic Agents
D000970 - Antineoplastic Agents
同义名列表
2 个代谢物同义名
数据库引用编号
9 个数据库交叉引用编号
- ChEBI: CHEBI:42588
- ChEBI: CHEBI:92493
- KEGGdrug: D04162
- PubChem: 5288209
- Metlin: METLIN43443
- DrugBank: DB05076
- ChEMBL: CHEMBL7301
- MeSH: Fenretinide
- CAS: 65646-68-6
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
0 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Ralston B Goldfarb, Matthew J Atala Pleshinger, David F Yan, Drew J Adams. Lipid-Restricted Culture Media Reveal Unexpected Cancer Cell Sensitivities.
ACS chemical biology.
2024 Apr; 19(4):896-907. doi:
10.1021/acschembio.3c00699. [PMID: 38506663] - Giovanna C Salata, Isabella D Malagó, Luciana B Lopes. A Lipid-Based In Situ-Forming Hexagonal Phase for Prolonged Retention and Drug Release in the Breast Tissue.
AAPS PharmSciTech.
2022 Sep; 23(7):260. doi:
10.1208/s12249-022-02411-9. [PMID: 36123553] - Alexsandra Conceição Apolinário, Giovanna Cassone Salata, Marcelo Medina de Souza, Marlus Chorilli, Luciana Biagini Lopes. Rethinking Breast Cancer Chemoprevention: Technological Advantages and Enhanced Performance of a Nanoethosomal-Based Hydrogel for Topical Administration of Fenretinide.
AAPS PharmSciTech.
2022 Apr; 23(4):104. doi:
10.1208/s12249-022-02257-1. [PMID: 35381947] - Anthony P Miller, Molly Black, Jaume Amengual. Fenretinide inhibits vitamin A formation from β-carotene and regulates carotenoid levels in mice.
Biochimica et biophysica acta. Molecular and cell biology of lipids.
2022 02; 1867(2):159070. doi:
10.1016/j.bbalip.2021.159070. [PMID: 34742949] - Yasuhiro Hayashi, Kiyoto Tsuchiya, Mizuki Yamamoto, Yoko Nemoto-Sasaki, Kazunari Tanigawa, Kotaro Hama, Yusuke Ueda, Takashi Tanikawa, Jin Gohda, Kenji Maeda, Jun-Ichiro Inoue, Atsushi Yamashita. N-(4-Hydroxyphenyl) Retinamide Suppresses SARS-CoV-2 Spike Protein-Mediated Cell-Cell Fusion by a Dihydroceramide Δ4-Desaturase 1-Independent Mechanism.
Journal of virology.
2021 08; 95(17):e0080721. doi:
10.1128/jvi.00807-21. [PMID: 34106748] - Jacob S Thomas, Anthony B El-Khoueiry, Barry J Maurer, Susan Groshen, Jacek K Pinski, Everardo Cobos, David R Gandara, Heinz J Lenz, Min H Kang, C Patrick Reynolds, Edward M Newman. A phase I study of intravenous fenretinide (4-HPR) for patients with malignant solid tumors.
Cancer chemotherapy and pharmacology.
2021 04; 87(4):525-532. doi:
10.1007/s00280-020-04224-8. [PMID: 33423090] - Yutong Wang, Yanfang Ding, Changyuan Wang, Meng Gao, Youwei Xu, Xiaodong Ma, Xinyi Ma, Hongxia Cui, Lei Li. Fenretinide-polyethylene glycol (PEG) conjugate with improved solubility enhanced cytotoxicity to cancer cell and potent in vivo efficacy.
Pharmaceutical development and technology.
2020 Oct; 25(8):962-970. doi:
10.1080/10837450.2020.1765377. [PMID: 32366203] - Yutong Wang, Yanfang Ding, Youwei Xu, Changyuan Wang, Yingying Ding, Meng Gao, Chengge Ma, Xiaodong Ma, Lei Li. Mixed micelles of TPGS and Soluplus® for co-delivery of paclitaxel and fenretinide: in vitro and in vivo anticancer study.
Pharmaceutical development and technology.
2020 Sep; 25(7):865-873. doi:
10.1080/10837450.2020.1753770. [PMID: 32266855] - Ilaria Patruno, Dawn Thompson, Sergio Dall'Angelo, Albert D Windhorst, Danielle J Vugts, Alex J Poot, Nimesh Mody, Matteo Zanda. Design, Synthesis, Radiosynthesis and Biological Evaluation of Fenretinide Analogues as Anticancer and Metabolic Syndrome-Preventive Agents.
ChemMedChem.
2020 08; 15(16):1579-1590. doi:
10.1002/cmdc.202000143. [PMID: 32497314] - Isabella Orienti, Giovanna Angela Gentilomi, Giovanna Farruggia. Pulmonary Delivery of Fenretinide: A Possible Adjuvant Treatment In COVID-19.
International journal of molecular sciences.
2020 May; 21(11):. doi:
10.3390/ijms21113812. [PMID: 32471278] - Mina Youssef, Juan B De Sanctis, Cynthia Kanagaratham, Shao Tao, Eisha Ahmed, Danuta Radzioch. Efficacy of Optimized Treatment Protocol Using LAU-7b Formulation against Ovalbumin (OVA) and House Dust Mite (HDM) -Induced Allergic Asthma in Atopic Hyperresponsive A/J Mice.
Pharmaceutical research.
2020 Jan; 37(2):31. doi:
10.1007/s11095-019-2743-z. [PMID: 31915990] - Marco Busnelli, Stefano Manzini, Fabrizia Bonacina, Sabina Soldati, Silvia Stella Barbieri, Patrizia Amadio, Leonardo Sandrini, Francesca Arnaboldi, Elena Donetti, Reijo Laaksonen, Saverio Paltrinieri, Eugenio Scanziani, Giulia Chiesa. Fenretinide treatment accelerates atherosclerosis development in apoE-deficient mice in spite of beneficial metabolic effects.
British journal of pharmacology.
2020 01; 177(2):328-345. doi:
10.1111/bph.14869. [PMID: 31621898] - Isabella Orienti, Valentina Salvati, Giovanni Sette, Massimo Zucchetti, Lucilla Bongiorno-Borbone, Angelo Peschiaroli, Lello Zolla, Federica Francescangeli, Mariella Ferrari, Cristina Matteo, Ezia Bello, Antonio Di Virgilio, Mario Falchi, Maria Laura De Angelis, Marta Baiocchi, Gerry Melino, Ruggero De Maria, Ann Zeuner, Adriana Eramo. A novel oral micellar fenretinide formulation with enhanced bioavailability and antitumour activity against multiple tumours from cancer stem cells.
Journal of experimental & clinical cancer research : CR.
2019 Aug; 38(1):373. doi:
10.1186/s13046-019-1383-9. [PMID: 31439019] - Ruta Dekeryte, Claire Hull, Kaja Plucińska, Shakil Khan, Sarah Kamli-Salino, Nimesh Mody, Nicola Morrice, Chris McLaughlin, Victor Gault, Bettina Platt, Mirela Delibegovic. Effects of Liraglutide and Fenretinide treatments on the diabetic phenotype of neuronal human BACE1 knock-in mice.
Biochemical pharmacology.
2019 08; 166(?):222-230. doi:
10.1016/j.bcp.2019.05.020. [PMID: 31103416] - Aalekhya Reddam, Constance A Mitchell, Subham Dasgupta, Jay S Kirkwood, Alyssa Vollaro, Manhoi Hur, David C Volz. mRNA-Sequencing Identifies Liver as a Potential Target Organ for Triphenyl Phosphate in Embryonic Zebrafish.
Toxicological sciences : an official journal of the Society of Toxicology.
2019 Jul; ?(?):. doi:
10.1093/toxsci/kfz169. [PMID: 31368501] - Isabella Orienti, Federica Francescangeli, Maria Laura De Angelis, Katia Fecchi, Lucilla Bongiorno-Borbone, Michele Signore, Angelo Peschiaroli, Alessandra Boe, Alessandro Bruselles, Angelita Costantino, Adriana Eramo, Valentina Salvati, Giovanni Sette, Paola Contavalli, Lello Zolla, Toshihiko Oki, Toshio Kitamura, Massimo Spada, Alessandro Giuliani, Marta Baiocchi, Filippo La Torre, Gerry Melino, Marco Tartaglia, Ruggero De Maria, Ann Zeuner. A new bioavailable fenretinide formulation with antiproliferative, antimetabolic, and cytotoxic effects on solid tumors.
Cell death & disease.
2019 07; 10(7):529. doi:
10.1038/s41419-019-1775-y. [PMID: 31332161] - Arvin B Tam, Lindsay S Roberts, Vivek Chandra, Io Guane Rivera, Daniel K Nomura, Douglass J Forbes, Maho Niwa. The UPR Activator ATF6 Responds to Proteotoxic and Lipotoxic Stress by Distinct Mechanisms.
Developmental cell.
2018 08; 46(3):327-343.e7. doi:
10.1016/j.devcel.2018.04.023. [PMID: 30086303] - Xiao Qing Wang, Zhou-Na Li, Qi-Ming Wang, Hong-Yan Jin, Zhonggao Gao, Zhe-Hu Jin. Lipid nano-bubble combined with ultrasound for anti-keloids therapy.
Journal of liposome research.
2018 Mar; 28(1):5-13. doi:
10.1080/08982104.2016.1239633. [PMID: 27733083] - Ann M Mohrbacher, Allen S Yang, Susan Groshen, Shivaani Kummar, Martin E Gutierrez, Min H Kang, Denice Tsao-Wei, C Patrick Reynolds, Edward M Newman, Barry J Maurer. Phase I Study of Fenretinide Delivered Intravenously in Patients with Relapsed or Refractory Hematologic Malignancies: A California Cancer Consortium Trial.
Clinical cancer research : an official journal of the American Association for Cancer Research.
2017 Aug; 23(16):4550-4555. doi:
10.1158/1078-0432.ccr-17-0234. [PMID: 28420721] - Lluis Lopez-Barcons, Barry J Maurer, Min H Kang, C Patrick Reynolds. P450 inhibitor ketoconazole increased the intratumor drug levels and antitumor activity of fenretinide in human neuroblastoma xenograft models.
International journal of cancer.
2017 07; 141(2):405-413. doi:
10.1002/ijc.30706. [PMID: 28340497] - Jason P Cooper, C Patrick Reynolds, Hwangeui Cho, Min H Kang. Clinical development of fenretinide as an antineoplastic drug: Pharmacology perspectives.
Experimental biology and medicine (Maywood, N.J.).
2017 06; 242(11):1178-1184. doi:
10.1177/1535370217706952. [PMID: 28429653] - Nicola Morrice, George D Mcilroy, Seshu R Tammireddy, Jennifer Reekie, Kirsty D Shearer, Mary K Doherty, Mirela Delibegović, Phillip D Whitfield, Nimesh Mody. Elevated Fibroblast growth factor 21 (FGF21) in obese, insulin resistant states is normalised by the synthetic retinoid Fenretinide in mice.
Scientific reports.
2017 03; 7(?):43782. doi:
10.1038/srep43782. [PMID: 28256636] - Hwang Eui Cho, H Kang Min. Analysis of fenretinide and its metabolites in human plasma by liquid chromatography-tandem mass spectrometry and its application to clinical pharmacokinetics.
Journal of pharmaceutical and biomedical analysis.
2017 Jan; 132(?):117-124. doi:
10.1016/j.jpba.2016.09.046. [PMID: 27701038] - Matteo Puntoni, Marilena Petrera, Sara Campora, Elsa Garrone, Carlotta Defferrari, Rosalba Torrisi, Harriet Johansson, Silvia Bruno, Antonio Curotto, Andrea DeCensi. Prognostic Significance of VEGF after Twenty-Year Follow-up in a Randomized Trial of Fenretinide in Non-Muscle-Invasive Bladder Cancer.
Cancer prevention research (Philadelphia, Pa.).
2016 06; 9(6):437-44. doi:
10.1158/1940-6207.capr-15-0345. [PMID: 27045034] - Elizabeth Roundhill, Doug Turnbull, Susan Burchill. Localization of MRP-1 to the outer mitochondrial membrane by the chaperone protein HSP90β.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology.
2016 05; 30(5):1712-23. doi:
10.1096/fj.15-283408. [PMID: 26722004] - George D Mcilroy, Seshu R Tammireddy, Benjamin H Maskrey, Louise Grant, Mary K Doherty, David G Watson, Mirela Delibegović, Phillip D Whitfield, Nimesh Mody. Fenretinide mediated retinoic acid receptor signalling and inhibition of ceramide biosynthesis regulates adipogenesis, lipid accumulation, mitochondrial function and nutrient stress signalling in adipocytes and adipose tissue.
Biochemical pharmacology.
2016 Jan; 100(?):86-97. doi:
10.1016/j.bcp.2015.11.017. [PMID: 26592777] - Margot Carocci, Stephen M Hinshaw, Mary A Rodgers, Valerie A Villareal, Dominique J Burri, Rajendra Pilankatta, Natalya P Maharaj, Michaela U Gack, Eric J Stavale, Kelly L Warfield, Priscilla L Yang. The bioactive lipid 4-hydroxyphenyl retinamide inhibits flavivirus replication.
Antimicrobial agents and chemotherapy.
2015 Jan; 59(1):85-95. doi:
10.1128/aac.04177-14. [PMID: 25313218] - Johanna E Fraser, Satoru Watanabe, Chunxiao Wang, Wing Ki Kitti Chan, Belinda Maher, Adam Lopez-Denman, Caroline Hick, Kylie M Wagstaff, Jason M Mackenzie, Patrick M Sexton, Subhash G Vasudevan, David A Jans. A nuclear transport inhibitor that modulates the unfolded protein response and provides in vivo protection against lethal dengue virus infection.
The Journal of infectious diseases.
2014 Dec; 210(11):1780-91. doi:
10.1093/infdis/jiu319. [PMID: 24903662] - Nimesh Mody, George D Mcilroy. The mechanisms of Fenretinide-mediated anti-cancer activity and prevention of obesity and type-2 diabetes.
Biochemical pharmacology.
2014 Oct; 91(3):277-86. doi:
10.1016/j.bcp.2014.07.012. [PMID: 25069047] - Sandra Durante, Isabella Orienti, Gabriella Teti, Viviana Salvatore, Stefano Focaroli, Anna Tesei, Sara Pignatta, Mirella Falconi. Anti-tumor activity of fenretinide complexed with human serum albumin in lung cancer xenograft mouse model.
Oncotarget.
2014 Jul; 5(13):4811-20. doi:
10.18632/oncotarget.2038. [PMID: 25015569] - Yingcai Wang, Richard Connors, Pingchen Fan, Xiaodong Wang, Zhongyu Wang, Jiwen Liu, Frank Kayser, Julio C Medina, Sheree Johnstone, Haoda Xu, Stephen Thibault, Nigel Walker, Marion Conn, Ying Zhang, Qingxiang Liu, Mark P Grillo, Alykhan Motani, Peter Coward, Zhulun Wang. Structure-assisted discovery of the first non-retinoid ligands for Retinol-Binding Protein 4.
Bioorganic & medicinal chemistry letters.
2014 Jul; 24(13):2885-91. doi:
10.1016/j.bmcl.2014.04.089. [PMID: 24835984] - Barry J Maurer, Min H Kang, Judith G Villablanca, Jitka Janeba, Susan Groshen, Katherine K Matthay, Paul M Sondel, John M Maris, Hollie A Jackson, Fariba Goodarzian, Hiroyuki Shimada, Scarlett Czarnecki, Beth Hasenauer, C Patrick Reynolds, Araz Marachelian. Phase I trial of fenretinide delivered orally in a novel organized lipid complex in patients with relapsed/refractory neuroblastoma: a report from the New Approaches to Neuroblastoma Therapy (NANT) consortium.
Pediatric blood & cancer.
2013 Nov; 60(11):1801-8. doi:
10.1002/pbc.24643. [PMID: 23813912] - Nathan L Mata, Jay B Lichter, Roger Vogel, Yun Han, Tam V Bui, Lawrence J Singerman. Investigation of oral fenretinide for treatment of geographic atrophy in age-related macular degeneration.
Retina (Philadelphia, Pa.).
2013 Mar; 33(3):498-507. doi:
10.1097/iae.0b013e318265801d. [PMID: 23023528] - George D Mcilroy, Mirela Delibegovic, Carl Owen, Patrick N Stoney, Kirsty D Shearer, Peter J McCaffery, Nimesh Mody. Fenretinide treatment prevents diet-induced obesity in association with major alterations in retinoid homeostatic gene expression in adipose, liver, and hypothalamus.
Diabetes.
2013 Mar; 62(3):825-36. doi:
10.2337/db12-0458. [PMID: 23193184] - Nicoleta Dobri, Qiong Qin, Jian Kong, Kazunori Yamamoto, Zhao Liu, Gennadiy Moiseyev, Jian-Xing Ma, Rando Allikmets, Janet R Sparrow, Konstantin Petrukhin. A1120, a nonretinoid RBP4 antagonist, inhibits formation of cytotoxic bisretinoids in the animal model of enhanced retinal lipofuscinogenesis.
Investigative ophthalmology & visual science.
2013 Jan; 54(1):85-95. doi:
10.1167/iovs.12-10050. [PMID: 23211825] - Hong Yu, Michael Valerio, Jacek Bielawski. Fenretinide inhibited de novo ceramide synthesis and proinflammatory cytokines induced by Aggregatibacter actinomycetemcomitans.
Journal of lipid research.
2013 Jan; 54(1):189-201. doi:
10.1194/jlr.m031427. [PMID: 23139430] - Benjamin T Bikman, Yuguang Guan, Guanghou Shui, M Mobin Siddique, William L Holland, Ji Yun Kim, Gemma Fabriàs, Markus R Wenk, Scott A Summers. Fenretinide prevents lipid-induced insulin resistance by blocking ceramide biosynthesis.
The Journal of biological chemistry.
2012 May; 287(21):17426-17437. doi:
10.1074/jbc.m112.359950. [PMID: 22474281] - Aintzane Apraiz, Jolanta Idkowiak-Baldys, Naiara Nieto-Rementería, María Dolores Boyano, Yusuf A Hannun, Aintzane Asumendi. Dihydroceramide accumulation and reactive oxygen species are distinct and nonessential events in 4-HPR-mediated leukemia cell death.
Biochemistry and cell biology = Biochimie et biologie cellulaire.
2012 Apr; 90(2):209-23. doi:
10.1139/o2012-001. [PMID: 22428532] - E A Roundhill, S A Burchill. Detection and characterisation of multi-drug resistance protein 1 (MRP-1) in human mitochondria.
British journal of cancer.
2012 Mar; 106(6):1224-33. doi:
10.1038/bjc.2012.40. [PMID: 22353810] - Roberta Carosio, Vito Pistoia, Isabella Orienti, Franca Formelli, Elena Cavadini, Salvatore Mangraviti, Paolo G Montaldo, Emanuela Ognio, Laura Emionite, Guendalina Zuccari. Enhanced anti-neuroblastoma activity of a fenretinide complexed form after intravenous administration.
The Journal of pharmacy and pharmacology.
2012 Feb; 64(2):228-36. doi:
10.1111/j.2042-7158.2011.01403.x. [PMID: 22221098] - Justyna Szumiło, Justyna Podlodowska, Wiktor Podlodowski, Elzbieta Starosławska, Franciszek Burdan. [Chemoprevention of oral cancer--clinical and experimental studies].
Polski merkuriusz lekarski : organ Polskiego Towarzystwa Lekarskiego.
2012 Feb; 32(188):138-42. doi:
". [PMID: 22590920] - Debora Macis, Sara Gandini, Aliana Guerrieri-Gonzaga, Harriet Johansson, Paolo Magni, Massimiliano Ruscica, Matteo Lazzeroni, Davide Serrano, Massimiliano Cazzaniga, Serena Mora, Irene Feroce, Maria Pizzamiglio, Maria Teresa Sandri, Marcella Gulisano, Bernardo Bonanni, Andrea Decensi. Prognostic effect of circulating adiponectin in a randomized 2 x 2 trial of low-dose tamoxifen and fenretinide in premenopausal women at risk for breast cancer.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology.
2012 Jan; 30(2):151-7. doi:
10.1200/jco.2011.35.2237. [PMID: 22162577] - In-uk Koh, Hye-Seung Jun, Joo Sun Choi, Joo Hyun Lim, Won Ho Kim, Jong Bok Yoon, Jihyun Song. Fenretinide ameliorates insulin resistance and fatty liver in obese mice.
Biological & pharmaceutical bulletin.
2012; 35(3):369-75. doi:
10.1248/bpb.35.369. [PMID: 22382323] - Eugenia Poliakov, Alexander Gubin, James Laird, Susan Gentleman, Robert G Salomon, T Michael Redmond. The mechanism of fenretinide (4-HPR) inhibition of β-carotene monooxygenase 1. New suspect for the visual side effects of fenretinide.
Advances in experimental medicine and biology.
2012; 723(?):167-74. doi:
10.1007/978-1-4614-0631-0_23. [PMID: 22183330] - Judith G Villablanca, Wendy B London, Arlene Naranjo, Patrick McGrady, Matthew M Ames, Joel M Reid, Renee M McGovern, Sarah A Buhrow, Hollie Jackson, Enno Stranzinger, Brenda J Kitchen, Paul M Sondel, Marguerite T Parisi, Barry Shulkin, Gregory A Yanik, Susan L Cohn, C Patrick Reynolds. Phase II study of oral capsular 4-hydroxyphenylretinamide (4-HPR/fenretinide) in pediatric patients with refractory or recurrent neuroblastoma: a report from the Children's Oncology Group.
Clinical cancer research : an official journal of the American Association for Cancer Research.
2011 Nov; 17(21):6858-66. doi:
10.1158/1078-0432.ccr-11-0995. [PMID: 21908574] - Nishant Mohan, Naren L Banik, Swapan K Ray. Combination of N-(4-hydroxyphenyl) retinamide and apigenin suppressed starvation-induced autophagy and promoted apoptosis in malignant neuroblastoma cells.
Neuroscience letters.
2011 Sep; 502(1):24-9. doi:
10.1016/j.neulet.2011.07.016. [PMID: 21801811] - José Angel Campos-Sandoval, Clara Redondo, Gemma K Kinsella, Akos Pal, Geraint Jones, Gwen S Eyre, Simon C Hirst, John B C Findlay. Fenretinide derivatives act as disrupters of interactions of serum retinol binding protein (sRBP) with transthyretin and the sRBP receptor.
Journal of medicinal chemistry.
2011 Jul; 54(13):4378-87. doi:
10.1021/jm200256g. [PMID: 21591606] - Jason P Cooper, Kyunghwa Hwang, Hardeep Singh, Dong Wang, C Patrick Reynolds, Robert W Curley, Simon C Williams, Barry J Maurer, Min H Kang. Fenretinide metabolism in humans and mice: utilizing pharmacological modulation of its metabolic pathway to increase systemic exposure.
British journal of pharmacology.
2011 Jul; 163(6):1263-75. doi:
10.1111/j.1476-5381.2011.01310.x. [PMID: 21391977] - Shivaani Kummar, Martin E Gutierrez, Barry J Maurer, C Patrick Reynolds, Min Kang, Hardeep Singh, Sonja Crandon, Anthony J Murgo, James H Doroshow. Phase I trial of fenretinide lym-x-sorb oral powder in adults with solid tumors and lymphomas.
Anticancer research.
2011 Mar; 31(3):961-6. doi:
NULL. [PMID: 21498721] - N A Illingworth, A V Boddy, A K Daly, G J Veal. Characterization of the metabolism of fenretinide by human liver microsomes, cytochrome P450 enzymes and UDP-glucuronosyltransferases.
British journal of pharmacology.
2011 Feb; 162(4):989-99. doi:
10.1111/j.1476-5381.2010.01104.x. [PMID: 21054342] - Franca Formelli, Elena Cavadini, Roberto Luksch, Alberto Garaventa, Valentina Appierto, Stefano Persiani. Relationship among pharmacokinetics and pharmacodynamics of fenretinide and plasma retinol reduction in neuroblastoma patients.
Cancer chemotherapy and pharmacology.
2010 Oct; 66(5):993-8. doi:
10.1007/s00280-010-1370-5. [PMID: 20532509] - Manuela Valsecchi, Massimo Aureli, Laura Mauri, Giuditta Illuzzi, Vanna Chigorno, Alessandro Prinetti, Sandro Sonnino. Sphingolipidomics of A2780 human ovarian carcinoma cells treated with synthetic retinoids.
Journal of lipid research.
2010 Jul; 51(7):1832-40. doi:
10.1194/jlr.m004010. [PMID: 20194109] - Numsen Hail, Ping Chen, Jadwiga J Kepa, Lane R Bushman, Colin Shearn. Dihydroorotate dehydrogenase is required for N-(4-hydroxyphenyl)retinamide-induced reactive oxygen species production and apoptosis.
Free radical biology & medicine.
2010 Jul; 49(1):109-16. doi:
10.1016/j.freeradbiomed.2010.04.006. [PMID: 20399851] - Rubèn López-Vales, Adriana Redensek, Thomas A A Skinner, Khizr I Rathore, Nader Ghasemlou, Gabriella Wojewodka, Juan DeSanctis, Danuta Radzioch, Samuel David. Fenretinide promotes functional recovery and tissue protection after spinal cord contusion injury in mice.
The Journal of neuroscience : the official journal of the Society for Neuroscience.
2010 Mar; 30(9):3220-6. doi:
10.1523/jneurosci.5770-09.2010. [PMID: 20203181] - Bryan J Schneider, Francis P Worden, Shirish M Gadgeel, Ralph E Parchment, Collette M Hodges, James Zwiebel, Rodney L Dunn, Antoinette J Wozniak, Michael J Kraut, Gregory P Kalemkerian. Phase II trial of fenretinide (NSC 374551) in patients with recurrent small cell lung cancer.
Investigational new drugs.
2009 Dec; 27(6):571-8. doi:
10.1007/s10637-009-9228-6. [PMID: 19225720] - Valentina Appierto, Paola Tiberio, Elena Cavadini, Patrizia Casalini, Graziella Cappelletti, Franca Formelli. Antimitotic effect of the retinoid 4-oxo-fenretinide through inhibition of tubulin polymerization: a novel mechanism of retinoid growth-inhibitory activity.
Molecular cancer therapeutics.
2009 Dec; 8(12):3360-8. doi:
10.1158/1535-7163.mct-09-0798. [PMID: 19996280] - Frederic Preitner, Nimesh Mody, Timothy E Graham, Odile D Peroni, Barbara B Kahn. Long-term Fenretinide treatment prevents high-fat diet-induced obesity, insulin resistance, and hepatic steatosis.
American journal of physiology. Endocrinology and metabolism.
2009 Dec; 297(6):E1420-9. doi:
10.1152/ajpendo.00362.2009. [PMID: 19826103] - Xin Li, Wen Ling, Angela Pennisi, Sharmin Khan, Shmuel Yaccoby. Fenretinide inhibits myeloma cell growth, osteoclastogenesis and osteoclast viability.
Cancer letters.
2009 Nov; 284(2):175-81. doi:
10.1016/j.canlet.2009.04.022. [PMID: 19446953] - Andrea Decensi, Chris Robertson, Aliana Guerrieri-Gonzaga, Davide Serrano, Massimiliano Cazzaniga, Serena Mora, Marcella Gulisano, Harriet Johansson, Viviana Galimberti, Enrico Cassano, Simona M Moroni, Franca Formelli, Ernst A Lien, Giuseppe Pelosi, Karen A Johnson, Bernardo Bonanni. Randomized double-blind 2 x 2 trial of low-dose tamoxifen and fenretinide for breast cancer prevention in high-risk premenopausal women.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology.
2009 Aug; 27(23):3749-56. doi:
10.1200/jco.2008.19.3797. [PMID: 19597031] - Claudine Guilbault, Gabriella Wojewodka, Zienab Saeed, Marian Hajduch, Elias Matouk, Juan B De Sanctis, Danuta Radzioch. Cystic fibrosis fatty acid imbalance is linked to ceramide deficiency and corrected by fenretinide.
American journal of respiratory cell and molecular biology.
2009 Jul; 41(1):100-6. doi:
10.1165/rcmb.2008-0279oc. [PMID: 19059886] - Peter Coward, Marion Conn, Jie Tang, Fei Xiong, Anthony Menjares, Jeff D Reagan. Application of an allosteric model to describe the interactions among retinol binding protein 4, transthyretin, and small molecule retinol binding protein 4 ligands.
Analytical biochemistry.
2009 Jan; 384(2):312-20. doi:
10.1016/j.ab.2008.09.051. [PMID: 18952041] - Franca Formelli, Elisabetta Meneghini, Elena Cavadini, Tiziana Camerini, Maria G Di Mauro, Giuseppe De Palo, Umberto Veronesi, Franco Berrino, Andrea Micheli. Plasma retinol and prognosis of postmenopausal breast cancer patients.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2009 Jan; 18(1):42-8. doi:
10.1158/1055-9965.epi-08-0496. [PMID: 19124479] - William N William, J Jack Lee, Scott M Lippman, Jack W Martin, Nitin Chakravarti, Hai T Tran, Anita L Sabichi, Edward S Kim, Lei Feng, Reuben Lotan, Vassiliki A Papadimitrakopoulou. High-dose fenretinide in oral leukoplakia.
Cancer prevention research (Philadelphia, Pa.).
2009 Jan; 2(1):22-6. doi:
10.1158/1940-6207.capr-08-0100. [PMID: 19139014] - Eric Cheung, Jacek Pinski, Tanya Dorff, Susan Groshen, David I Quinn, C Patrick Reynolds, Barry J Maurer, Primo N Lara, Denice D Tsao-Wei, Przemyslaw Twardowski, Gurkamal Chatta, Mark McNamara, David R Gandara. Oral fenretinide in biochemically recurrent prostate cancer: a California cancer consortium phase II trial.
Clinical genitourinary cancer.
2009 Jan; 7(1):43-50. doi:
10.3816/cgc.2009.n.008. [PMID: 19213668] - Daniela Di Paolo, Monica Loi, Fabio Pastorino, Chiara Brignole, Danilo Marimpietri, Pamela Becherini, Irene Caffa, Alessia Zorzoli, Renato Longhi, Cristina Gagliani, Carlo Tacchetti, Angelo Corti, Theresa M Allen, Mirco Ponzoni, Gabriella Pagnan. Liposome-mediated therapy of neuroblastoma.
Methods in enzymology.
2009; 465(?):225-49. doi:
10.1016/s0076-6879(09)65012-6. [PMID: 19913170] - Harriet Johansson, Sara Gandini, Aliana Guerrieri-Gonzaga, Simona Iodice, Massimiliano Ruscica, Bernardo Bonanni, Marcella Gulisano, Paolo Magni, Franca Formelli, Andrea Decensi. Effect of fenretinide and low-dose tamoxifen on insulin sensitivity in premenopausal women at high risk for breast cancer.
Cancer research.
2008 Nov; 68(22):9512-8. doi:
10.1158/0008-5472.can-08-0553. [PMID: 19010927] - Michael F Marmor, Atul Jain, Darius Moshfeghi. Total rod ERG suppression with high dose compassionate Fenretinide usage.
Documenta ophthalmologica. Advances in ophthalmology.
2008 Nov; 117(3):257-61. doi:
10.1007/s10633-008-9132-y. [PMID: 18523815] - Franca Formelli, Elena Cavadini, Roberto Luksch, Alberto Garaventa, Maria Grazia Villani, Valentina Appierto, Stefano Persiani. Pharmacokinetics of oral fenretinide in neuroblastoma patients: indications for optimal dose and dosing schedule also with respect to the active metabolite 4-oxo-fenretinide.
Cancer chemotherapy and pharmacology.
2008 Sep; 62(4):655-65. doi:
10.1007/s00280-007-0649-7. [PMID: 18066548] - Zienab Saeed, Claudine Guilbault, Juan B De Sanctis, Jennifer Henri, Dominique Marion, René St-Arnaud, Danuta Radzioch. Fenretinide prevents the development of osteoporosis in Cftr-KO mice.
Journal of cystic fibrosis : official journal of the European Cystic Fibrosis Society.
2008 May; 7(3):222-30. doi:
10.1016/j.jcf.2007.09.001. [PMID: 17988958] - Parameswaran G Sreekumar, Jiehao Zhou, Joonhong Sohn, Christine Spee, Stephen J Ryan, Barry J Maurer, Ram Kannan, David R Hinton. N-(4-hydroxyphenyl) retinamide augments laser-induced choroidal neovascularization in mice.
Investigative ophthalmology & visual science.
2008 Mar; 49(3):1210-20. doi:
10.1167/iovs.07-0667. [PMID: 18326751] - James I Lee, Vu T Nguyen, Mei-Ling Chen, Peter C Adamson. A rapid, sensitive and selective liquid chromatography/atmospheric pressure chemical ionization tandem mass spectrometry method for determination of fenretinide (4-HPR) in plasma.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2008 Feb; 862(1-2):64-71. doi:
10.1016/j.jchromb.2007.10.044. [PMID: 18032119] - Claudine Guilbault, Juan B De Sanctis, Gabriella Wojewodka, Zienab Saeed, Claude Lachance, Thomas A A Skinner, Regina M Vilela, Stan Kubow, Larry C Lands, Marian Hajduch, Elias Matouk, Danuta Radzioch. Fenretinide corrects newly found ceramide deficiency in cystic fibrosis.
American journal of respiratory cell and molecular biology.
2008 Jan; 38(1):47-56. doi:
10.1165/rcmb.2007-0036oc. [PMID: 17656682] - Amit Kokate, Xiaoling Li, Bhaskara Jasti. Transport of a novel anti-cancer agent, fenretinide across Caco-2 monolayers.
Investigational new drugs.
2007 Jun; 25(3):197-203. doi:
10.1007/s10637-006-9026-3. [PMID: 17146731] - Barry J Maurer, Ondrej Kalous, David W Yesair, Xiaqin Wu, Jitka Janeba, Vanessa Maldonado, Vazgen Khankaldyyan, Tomas Frgala, Bee-Chun Sun, R Travis McKee, Stephen W Burgess, Walter A Shaw, C Patrick Reynolds. Improved oral delivery of N-(4-hydroxyphenyl)retinamide with a novel LYM-X-SORB organized lipid complex.
Clinical cancer research : an official journal of the American Association for Cancer Research.
2007 May; 13(10):3079-86. doi:
10.1158/1078-0432.ccr-06-1889. [PMID: 17505011] - Rainer Kuefer, Felicitas Genze, Waltraud Zugmaier, Richard E Hautmann, Ludwig Rinnab, Juergen E Gschwend, Marina Angelmeier, Aidee Estrada, Berthold Buechele. Antagonistic effects of sodium butyrate and N-(4-hydroxyphenyl)-retinamide on prostate cancer.
Neoplasia (New York, N.Y.).
2007 Mar; 9(3):246-53. doi:
10.1593/neo.06766. [PMID: 17401464] - Suryakant K Niture, Chinavenmani S Velu, Quentin R Smith, G Jayarama Bhat, Kalkunte S Srivenugopal. Increased expression of the MGMT repair protein mediated by cysteine prodrugs and chemopreventative natural products in human lymphocytes and tumor cell lines.
Carcinogenesis.
2007 Feb; 28(2):378-89. doi:
10.1093/carcin/bgl155. [PMID: 16950796] - Nicoletta Colombo, Franca Formelli, Maria Grazia Cantù, Gabriella Parma, Milena Gasco, Alessandra Argusti, Alfredo Santinelli, Rodolfo Montironi, Elena Cavadini, Laura Baglietto, Aliana Guerrieri-Gonzaga, Giuseppe Viale, Andrea Decensi. A phase I-II preoperative biomarker trial of fenretinide in ascitic ovarian cancer.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2006 Oct; 15(10):1914-9. doi:
10.1158/1055-9965.epi-06-0183. [PMID: 17035399] - Judith G Villablanca, Mark D Krailo, Matthew M Ames, Joel M Reid, Gregory H Reaman, C Patrick Reynolds, Patrick C Reynolds. Phase I trial of oral fenretinide in children with high-risk solid tumors: a report from the Children's Oncology Group (CCG 09709).
Journal of clinical oncology : official journal of the American Society of Clinical Oncology.
2006 Jul; 24(21):3423-30. doi:
10.1200/jco.2005.03.9271. [PMID: 16849757] - Catherine M Finnegan, Robert Blumenthal. Fenretinide inhibits HIV infection by promoting viral endocytosis.
Antiviral research.
2006 Feb; 69(2):116-23. doi:
10.1016/j.antiviral.2005.11.002. [PMID: 16375981] - Roxana A Radu, Yun Han, Tam V Bui, Steven Nusinowitz, Dean Bok, Jay Lichter, Ken Widder, Gabriel H Travis, Nathan L Mata. 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.
2005 Dec; 46(12):4393-401. doi:
10.1167/iovs.05-0820. [PMID: 16303925] - Doris M Benbrook, Scott A Kamelle, Suresh B Guruswamy, Stan A Lightfoot, Teresa L Rutledge, Natalie S Gould, Bethany N Hannafon, S Terence Dunn, K Darrell Berlin. Flexible heteroarotinoids (Flex-Hets) exhibit improved therapeutic ratios as anti-cancer agents over retinoic acid receptor agonists.
Investigational new drugs.
2005 Oct; 23(5):417-28. doi:
10.1007/s10637-005-2901-5. [PMID: 16133793] - Ulka Vaishampayan, Lance K Heilbrun, Ralph E Parchment, Vikash Jain, James Zwiebel, Ramesh R Boinpally, Patricia LoRusso, Maha Hussain. Phase II trial of fenretinide in advanced renal carcinoma.
Investigational new drugs.
2005 Mar; 23(2):179-85. doi:
10.1007/s10637-005-5864-7. [PMID: 15744595] - Vinay K Puduvalli, W K Alfred Yung, Kenneth R Hess, John G Kuhn, Morris D Groves, Victor A Levin, James Zwiebel, Susan M Chang, Timothy F Cloughesy, Larry Junck, Patrick Wen, Frank Lieberman, Charles A Conrad, Mark R Gilbert, Christina A Meyers, Vivien Liu, Minesh P Mehta, M Kelly Nicholas, Michael Prados. Phase II study of fenretinide (NSC 374551) in adults with recurrent malignant gliomas: A North American Brain Tumor Consortium study.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology.
2004 Nov; 22(21):4282-9. doi:
10.1200/jco.2004.09.096. [PMID: 15514370] - Catherine M Finnegan, Satinder S Rawat, Anu Puri, Ji Ming Wang, Francis W Ruscetti, Robert Blumenthal. Ceramide, a target for antiretroviral therapy.
Proceedings of the National Academy of Sciences of the United States of America.
2004 Oct; 101(43):15452-7. doi:
10.1073/pnas.0402874101. [PMID: 15489273] - Maria Grazia Villani, Valentina Appierto, Elena Cavadini, Manuela Valsecchi, Sandro Sonnino, Robert W Curley, Franca Formelli. Identification of the fenretinide metabolite 4-oxo-fenretinide present in human plasma and formed in human ovarian carcinoma cells through induction of cytochrome P450 26A1.
Clinical cancer research : an official journal of the American Association for Cancer Research.
2004 Sep; 10(18 Pt 1):6265-75. doi:
10.1158/1078-0432.ccr-04-0655. [PMID: 15448016] - Penny E Lovat, Federica Di Sano, Marco Corazzari, Barbara Fazi, Raffaele Perrone Donnorso, Andy D J Pearson, Andrew G Hall, Christopher P F Redfern, Mauro Piacentini. Gangliosides link the acidic sphingomyelinase-mediated induction of ceramide to 12-lipoxygenase-dependent apoptosis of neuroblastoma in response to fenretinide.
Journal of the National Cancer Institute.
2004 Sep; 96(17):1288-99. doi:
10.1093/jnci/djh254. [PMID: 15339967] - Hye-Sook Han, Youn-Ja Kwon, Si-Ho Park, Eun-Joo Kim, Young-Soy Rho, Hong-Sig Sin, Soo-Jong Um. Potent effect of 5-HPBR, a butanoate derivative of 4-HPR, on cell growth and apoptosis in cancer cells.
International journal of cancer.
2004 Mar; 109(1):58-64. doi:
10.1002/ijc.11643. [PMID: 14735468] - Jason S Chapman, Kevin L Weiss, Robert W Curley, Margaret A Highland, Margaret Clagett-Dame. Hydrolysis of 4-HPR to atRA occurs in vivo but is not required for retinamide-induced apoptosis.
Archives of biochemistry and biophysics.
2003 Nov; 419(2):234-43. doi:
10.1016/j.abb.2003.09.001. [PMID: 14592467] - Andrea Decensi, Umberto Veronesi, Rosalba Miceli, Harriet Johansson, Luigi Mariani, Tiziana Camerini, Maria Gaetana Di Mauro, Elena Cavadini, Giuseppe De Palo, Alberto Costa, Marjorie Perloff, Winfred F Malone, Franca Formelli. Relationships between plasma insulin-like growth factor-I and insulin-like growth factor binding protein-3 and second breast cancer risk in a prevention trial of fenretinide.
Clinical cancer research : an official journal of the American Association for Cancer Research.
2003 Oct; 9(13):4722-9. doi:
NULL. [PMID: 14581342] - Anita L Sabichi, Manual R Modiano, J Jack Lee, Yei-Mei Peng, Ming-Jing Xu, Hugo Villar, William S Dalton, Scott M Lippman. Breast tissue accumulation of retinamides in a randomized short-term study of fenretinide.
Clinical cancer research : an official journal of the American Association for Cancer Research.
2003 Jul; 9(7):2400-5. doi:
NULL. [PMID: 12855611] - Alberto Garaventa, Roberto Luksch, Maria Serena Lo Piccolo, Elena Cavadini, Paolo G Montaldo, Maria Rosa Pizzitola, Luca Boni, Mirco Ponzoni, Andrea Decensi, Bruno De Bernardi, Franca Fossati Bellani, Franca Formelli. Phase I trial and pharmacokinetics of fenretinide in children with neuroblastoma.
Clinical cancer research : an official journal of the American Association for Cancer Research.
2003 Jun; 9(6):2032-9. doi:
NULL. [PMID: 12796365] - Franca Formelli, Tiziana Camerini, Elena Cavadini, Valentina Appierto, Maria Grazia Villani, Alberto Costa, Giuseppe De Palo, Maria Gaetana Di Mauro, Umberto Veronesi. Fenretinide breast cancer prevention trial: drug and retinol plasma levels in relation to age and disease outcome.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2003 Jan; 12(1):34-41. doi:
NULL. [PMID: 12540501] - Anat Erdreich-Epstein, Linda B Tran, Nina N Bowman, Hongtao Wang, Myles C Cabot, Donald L Durden, Jitka Vlckova, C Patrick Reynolds, Monique F Stins, Susan Groshen, Melissa Millard. Ceramide signaling in fenretinide-induced endothelial cell apoptosis.
The Journal of biological chemistry.
2002 Dec; 277(51):49531-7. doi:
10.1074/jbc.m209962200. [PMID: 12388538] - Noriko Takahashi, Toshihiro Ohba, Shin-ichi Togashi, Tetsuya Fukui. Biological activity of p-methylaminophenol, an essential structural component of N-(4-hydroxyphenyl)retinamide, fenretinide.
Journal of biochemistry.
2002 Nov; 132(5):767-74. doi:
10.1093/oxfordjournals.jbchem.a003285. [PMID: 12417027] - A Asumendi, M C Morales, A Alvarez, J Aréchaga, G Pérez-Yarza. Implication of mitochondria-derived ROS and cardiolipin peroxidation in N-(4-hydroxyphenyl)retinamide-induced apoptosis.
British journal of cancer.
2002 Jun; 86(12):1951-6. doi:
10.1038/sj.bjc.6600356. [PMID: 12085192] - Amanda H Prowse, Lisa Vanderveer, Simon W F Milling, Zhong-Zong Pan, Roland L Dunbrack, Xiang-Xi Xu, Andrew K Godwin. OVCA2 is downregulated and degraded during retinoid-induced apoptosis.
International journal of cancer.
2002 May; 99(2):185-92. doi:
10.1002/ijc.10334. [PMID: 11979432] - Cristina Rodríguez-Burford, Vernon E Steele, Amy S Anderson, Cecil R Stockard, Heidi L Weiss, Isao Eto, Gary L Johanning, William E Grizzle, Clinton J Grubbs. Effects of body weight gain reduction resulting from chemopreventive agent treatment on mammary gland morphology.
Nutrition and cancer.
2002; 43(1):67-75. doi:
10.1207/s15327914nc431_8. [PMID: 12467137] - H Abou-Issa, R W Curley, G A Alshafie, K L Weiss, M Clagett-Dame, J S Chapman, S M Mershon. Chemotherapeutic evaluation of 4-hydroxybenzylretinone (4-HBR), a nonhydrolyzable C-linked analog of N-(4-hydroxyphenyl) retinamide (4-HPR) against mammary carcinogenesis.
Anticancer research.
2001 Nov; 21(6A):3839-44. doi:
NULL. [PMID: 11911255] - C P Reynolds, R S Lemons. Retinoid therapy of childhood cancer.
Hematology/oncology clinics of North America.
2001 Oct; 15(5):867-910. doi:
10.1016/s0889-8588(05)70256-2. [PMID: 11765378]