18F-EF5

EF-5 (disambiguation)EF-5 changed 443718730 EF5 structure.svg skin-invert-image 200px 2-(2-Nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide NSC-684681; EF-5 152721-37-4 correct CAS 389053 correct chemspider 344807 correct FDA 383HJ2T87O correct chemspider JGGDSDPOPRWSCX-UHFFFAOYSA-N O=[N+]([O-])c1nccn1CC(=O)NCC(F)(F)C(F)(F)F correct chemspider 1S/C8H7F5N4O3/c9-7(10,8(11,12)13)4-15-5(18)3-16-2-1-14-6(16)17(19)20/h1-2H,3-4H2,(H,15,18) 8 7 5 4 3 EF5 is a nitroimidazole derivative used in oncology research. Evans SM, Fraker D, Hahn SM, Gleason K, Jenkins WT, Jenkins K, Hwang WT, Zhang P, Mick R, Koch CJ 6 EF5 binding and clinical outcome in human soft tissue sarcomas International Journal of Radiation Oncology, Biology, Physics 64 3 922–7 March 2006 16458778 10.1016/j.ijrobp.2005.05.068 Due to its similarity in chemical structure to etanidazole, EF5 binds in cells displaying hypoxia. Lord EM, Harwell L, Koch CJ Detection of hypoxic cells by monoclonal antibody recognizing 2-nitroimidazole adducts Cancer Research 53 23 5721–6 December 1993 8242628 Non-labeled EF5 has been extensively used in immunohistochemical studies for several years and its hypoxia specificity has been comprehensively evaluated Koch CJ, Evans SM Optimizing hypoxia detection and treatment strategies Seminars in Nuclear Medicine 45 2 163–76 March 2015 25704388 10.1053/j.semnuclmed.2014.10.004 4365940 Koch CJ Measurement of absolute oxygen levels in cells and tissues using oxygen sensors and 2-nitroimidazole EF5 [1] Measurement of absolute oxygen levels in cells and tissues using oxygen sensors and 2-nitroimidazole EF5 Methods in Enzymology 352 3–31 2002 12125356 10.1016/s0076-6879(02)52003-6 Elsevier 978-0-12-182255-2 The 18F-radiolabeled derivative of EF5 is being studied for its possibility to be used in positron emission tomography (PET) to detect low levels of oxygen in brain tumors and several other malignant tumors. Ziemer LS, Evans SM, Kachur AV, Shuman AL, Cardi CA, Jenkins WT, Karp JS, Alavi A, Dolbier WR, Koch CJ 6 Noninvasive imaging of tumor hypoxia in rats using the 2-nitroimidazole 18F-EF5 European Journal of Nuclear Medicine and Molecular Imaging 30 2 259–66 February 2003 12552344 10.1007/s00259-002-1037-5 22002592 This can help show how a tumor will respond to treatment. Targeting tumor hypoxia in cancer treatment aims to overcome radiotherapy resistance of hypoxic tumors. Thus, a major clinical implication for 18F-EF5-PET imaging is expected to be guiding of radiotherapy dose modulation. Clinical studies on 18F-EF5-PET/CT imaging have indicated clinically acceptable biodistribution and dosimetric profile, Lin LL, Silvoniemi A, Stubbs JB, Rengan R, Suilamo S, Solin O, Divgi C, Eskola O, Sorger JM, Stabin MG, Kachur A, Hahn SM, Grönroos TJ, Forsback S, Evans SM, Koch CJ, Minn H 6 Radiation dosimetry and biodistribution of the hypoxia tracer (18)F-EF5 in oncologic patients Cancer Biotherapy & Radiopharmaceuticals 27 7 412–9 September 2012 22897720 10.1089/cbr.2011.1130 and in head and neck cancer also favorable imaging characteristics, Komar G, Seppänen M, Eskola O, Lindholm P, Grönroos TJ, Forsback S, Sipilä H, Evans SM, Solin O, Minn H 6 18F-EF5: a new PET tracer for imaging hypoxia in head and neck cancer Journal of Nuclear Medicine 49 12 1944–51 December 2008 18997048 10.2967/jnumed.108.053785 16561341 free prognostic value Komar G, Lehtiö K, Seppänen M, Eskola O, Levola H, Lindholm P, Sipilä H, Seppälä J, Grénman R, Solin O, Minn H 6 Prognostic value of tumour blood flow, [18F]EF5 and [18F]FDG PET/CT imaging in patients with head and neck cancer treated with radiochemotherapy European Journal of Nuclear Medicine and Molecular Imaging 41 11 2042–50 November 2014 24898846 10.1007/s00259-014-2818-3 6276936 and repeatability. Silvoniemi A, Suilamo S, Laitinen T, Forsback S, Löyttyniemi E, Vaittinen S, Saunavaara V, Solin O, Grönroos TJ, Minn H 6 Repeatability of tumour hypoxia imaging using [18F]EF5 PET/CT in head and neck cancer European Journal of Nuclear Medicine and Molecular Imaging 45 2 161–169 February 2018 29075831 5745570 10.1007/s00259-017-3857-3 A recent 18F-EF5-PET/MR study showed promising potential in detecting tumor hypoxia in cervical cancer.Narva Sara I. Seppänen Marko P. Raiko Juho R.H. Forsback Sarita J. Orte Katri J. Virtanen Johanna M. Hynninen Johanna Hietanen Sakari December 2021 Imaging of Tumor Hypoxia With 18F-EF5 PET/MRI in Cervical Cancer Clinical Nuclear Medicine en 46 12 952–957 10.1097/RLU.0000000000003914 34619699 1536-0229 free However, 18F-EF5-PET/CT is not feasible in imaging of ovarian cancer due to physiological intra-abdominal 18F-EF5-accumulation. Laasik M, Hynninen J, Forsback S, Noponen T, Seppänen M, Hietanen S The feasibility of [18F]EF5-PET/CT to image hypoxia in ovarian tumors: a clinical study EJNMMI Research 10 1 103 September 2020 32910291 7483702 10.1186/s13550-020-00689-z free Further studies evaluating the clinical use of 18F-EF5 PET imaging in head and neck cancer are ongoing. References Category:Diagnostic medical imaging Category:Nitroimidazoles Category:Pentafluoroethyl compounds