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Revision as of 18:06, 8 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per [[Misplaced Pages:WikiProject Chemicals/Chembox validation|Chem/Drugbox validati← Previous edit Latest revision as of 10:03, 3 June 2024 edit undoAdam Harangozó (talk | contribs)Extended confirmed users1,659 editsm added wikilinkTag: Visual edit 
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{{Other uses|EF-5 (disambiguation){{!}}EF-5}} {{Other uses|EF-5 (disambiguation){{!}}EF-5}}
{{Chembox {{Chembox
| Watchedfields = changed
| verifiedrevid = 443716950 | verifiedrevid = 443718730
| ImageFile = EF5 structure.svg | ImageFile = EF5 structure.svg
| ImageSize = 200px | ImageSize = 200px
| ImageAlt = | ImageAlt =
| IUPACName = 2-(2-Nitro-1''H''-imidazol-1-yl)-''N''-(2,2,3,3,3-pentafluoropropyl)acetamide | PIN = 2-(2-Nitro-1''H''-imidazol-1-yl)-''N''-(2,2,3,3,3-pentafluoropropyl)acetamide
| OtherNames = NSC-684681; EF-5 | OtherNames = NSC-684681; EF-5
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo = 152721-37-4 | CASNo = 152721-37-4
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 389053 | PubChem = 389053
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 344807 | ChemSpiderID = 344807
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 383HJ2T87O | UNII = 383HJ2T87O
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = JGGDSDPOPRWSCX-UHFFFAOYSA-N | StdInChIKey = JGGDSDPOPRWSCX-UHFFFAOYSA-N
| SMILES = O=()c1nccn1CC(=O)NCC(F)(F)C(F)(F)F | SMILES = O=()c1nccn1CC(=O)NCC(F)(F)C(F)(F)F
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI=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) | StdInChI=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)
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=8|H=7|F=5|N=4|O=3 | C=8 | H=7 | F=5 | N=4 | O=3
| Appearance = | Appearance =
| Density = | Density =
| MeltingPt = | MeltingPt =
| BoilingPt = | BoilingPt =
| Solubility = }} | Solubility = }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = }} | AutoignitionPt = }}
}} }}


'''EF5''' is a ] used in oncology research.<ref>{{cite journal | doi = 10.1016/j.ijrobp.2005.05.068 | author = Evans, Sydney M.; Fraker, Douglas; Hahn, Stephen M.; Gleason, Kristen; Jenkins, W. Timothy; Jenkins, Kevin; Hwang, Wei-Ting; Zhang, Paul; Mick, Rosemarie; Koch, Cameron J | title = EF5 binding and clinical outcome in human soft tissue sarcomas | journal = International Journal of Radiation Oncology, Biology, Physics | year = 2006 | volume = 64 | issue = 3 | pages = 922–927}}</ref> Due to its similarity in chemical structure to ], EF5 binds in cells displaying hypoxia.<ref>{{cite journal | title = Detection of hypoxic cells by monoclonal antibody recognizing 2-nitroimidazole adducts | author = Lord, Edith M.; Harwell, Lee; Koch, Cameron J. | journal = Cancer Research | year = 1993 | volume = 53 | issue = 23 | pages = 5721–5726 | pmid = 8242628}}</ref> '''EF5''' is a ] derivative used in oncology research.<ref>{{cite journal | vauthors = Evans SM, Fraker D, Hahn SM, Gleason K, Jenkins WT, Jenkins K, Hwang WT, Zhang P, Mick R, Koch CJ | display-authors = 6 | title = EF5 binding and clinical outcome in human soft tissue sarcomas | journal = International Journal of Radiation Oncology, Biology, Physics | volume = 64 | issue = 3 | pages = 922–7 | date = March 2006 | pmid = 16458778 | doi = 10.1016/j.ijrobp.2005.05.068 }}</ref> Due to its similarity in chemical structure to ], EF5 binds in cells displaying hypoxia.<ref>{{cite journal | vauthors = Lord EM, Harwell L, Koch CJ | title = Detection of hypoxic cells by monoclonal antibody recognizing 2-nitroimidazole adducts | journal = Cancer Research | volume = 53 | issue = 23 | pages = 5721–6 | date = December 1993 | pmid = 8242628 }}</ref>


The ]-] ] of EF5 is being studied for its possibility to be used in ] (PET) to detect low levels of oxygen in ].<ref>{{cite journal | doi = 10.1007/s00259-002-1037-5 | author = Ziemer, L. S.; Evans, S. M.; Kachur, A. V.; Shuman, A. L.; Cardi, C. A.; Jenkins, W. T.; Karp, J. S.; Alavi, A.; Dolbier, W. R.; Koch, C. J. | title = Noninvasive imaging of tumor hypoxia in rats using the 2-nitroimidazole 18F-EF5 | journal = European Journal of Nuclear Medicine and Molecular Imaging | year = 2003 | volume = 30 | issue = 2 | pages = 259–266 | pmid = 12552344}}</ref> This can help show how a tumor will respond to ]. Non-labeled EF5 has been extensively used in immunohistochemical studies for several years and its hypoxia specificity has been comprehensively evaluated<ref>{{cite journal | vauthors = Koch CJ, Evans SM | title = Optimizing hypoxia detection and treatment strategies | journal = Seminars in Nuclear Medicine | volume = 45 | issue = 2 | pages = 163–76 | date = March 2015 | pmid = 25704388 | doi = 10.1053/j.semnuclmed.2014.10.004 | pmc = 4365940 }}</ref><ref>{{cite book | vauthors = Koch CJ | title = Measurement of absolute oxygen levels in cells and tissues using oxygen sensors and 2-nitroimidazole EF5 | chapter = &#91;1&#93; Measurement of absolute oxygen levels in cells and tissues using oxygen sensors and 2-nitroimidazole EF5 | series = Methods in Enzymology | volume = 352 | pages = 3–31 | date = 2002 | pmid = 12125356 | doi = 10.1016/s0076-6879(02)52003-6 | publisher = Elsevier | isbn = 978-0-12-182255-2 }}</ref> The ]-] ] of EF5 is being studied for its possibility to be used in ] (PET) to detect low levels of oxygen in ] and several other malignant tumors.<ref>{{cite journal | vauthors = Ziemer LS, Evans SM, Kachur AV, Shuman AL, Cardi CA, Jenkins WT, Karp JS, Alavi A, Dolbier WR, Koch CJ | display-authors = 6 | title = Noninvasive imaging of tumor hypoxia in rats using the 2-nitroimidazole 18F-EF5 | journal = European Journal of Nuclear Medicine and Molecular Imaging | volume = 30 | issue = 2 | pages = 259–66 | date = February 2003 | pmid = 12552344 | doi = 10.1007/s00259-002-1037-5 | s2cid = 22002592 }}</ref> This can help show how a tumor will respond to ].


Targeting tumor hypoxia in cancer treatment aims to overcome radiotherapy resistance of hypoxic tumors. Thus, a major clinical implication for <sup>18</sup>F-EF5-PET imaging is expected to be guiding of radiotherapy dose modulation. Clinical studies on <sup>18</sup>F-EF5-PET/CT imaging have indicated clinically acceptable biodistribution and dosimetric profile,<ref>{{cite journal | vauthors = 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 | display-authors = 6 | title = Radiation dosimetry and biodistribution of the hypoxia tracer (18)F-EF5 in oncologic patients | journal = Cancer Biotherapy & Radiopharmaceuticals | volume = 27 | issue = 7 | pages = 412–9 | date = September 2012 | pmid = 22897720 | doi = 10.1089/cbr.2011.1130 }}</ref> and in ] also favorable imaging characteristics,<ref>{{cite journal | vauthors = Komar G, Seppänen M, Eskola O, Lindholm P, Grönroos TJ, Forsback S, Sipilä H, Evans SM, Solin O, Minn H | display-authors = 6 | title = 18F-EF5: a new PET tracer for imaging hypoxia in head and neck cancer | journal = Journal of Nuclear Medicine | volume = 49 | issue = 12 | pages = 1944–51 | date = December 2008 | pmid = 18997048 | doi = 10.2967/jnumed.108.053785 | s2cid = 16561341 | doi-access = free }}</ref> prognostic value<ref>{{cite journal | vauthors = Komar G, Lehtiö K, Seppänen M, Eskola O, Levola H, Lindholm P, Sipilä H, Seppälä J, Grénman R, Solin O, Minn H | display-authors = 6 | title = Prognostic value of tumour blood flow, EF5 and FDG PET/CT imaging in patients with head and neck cancer treated with radiochemotherapy | journal = European Journal of Nuclear Medicine and Molecular Imaging | volume = 41 | issue = 11 | pages = 2042–50 | date = November 2014 | pmid = 24898846 | doi = 10.1007/s00259-014-2818-3 | s2cid = 6276936 }}</ref> and repeatability.<ref>{{cite journal | vauthors = Silvoniemi A, Suilamo S, Laitinen T, Forsback S, Löyttyniemi E, Vaittinen S, Saunavaara V, Solin O, Grönroos TJ, Minn H | display-authors = 6 | title = Repeatability of tumour hypoxia imaging using EF5 PET/CT in head and neck cancer | journal = European Journal of Nuclear Medicine and Molecular Imaging | volume = 45 | issue = 2 | pages = 161–169 | date = February 2018 | pmid = 29075831 | pmc = 5745570 | doi = 10.1007/s00259-017-3857-3 }}</ref> A recent 18F-EF5-PET/MR study showed promising potential in detecting tumor hypoxia in cervical cancer.<ref>{{Cite journal|last1=Narva|first1=Sara I.|last2=Seppänen|first2=Marko P.|last3=Raiko|first3=Juho R.H.|last4=Forsback|first4=Sarita J.|last5=Orte|first5=Katri J.|last6=Virtanen|first6=Johanna M.|last7=Hynninen|first7=Johanna|last8=Hietanen|first8=Sakari|date=December 2021|title=Imaging of Tumor Hypoxia With 18F-EF5 PET/MRI in Cervical Cancer|journal=Clinical Nuclear Medicine|language=en|volume=46|issue=12|pages=952–957|doi=10.1097/RLU.0000000000003914|pmid=34619699 |issn=1536-0229|doi-access=free}}</ref> However, <sup>18</sup>F-EF5-PET/CT is not feasible in imaging of ovarian cancer due to physiological intra-abdominal <sup>18</sup>F-EF5-accumulation.<ref>{{cite journal | vauthors = Laasik M, Hynninen J, Forsback S, Noponen T, Seppänen M, Hietanen S | title = The feasibility of EF5-PET/CT to image hypoxia in ovarian tumors: a clinical study | journal = EJNMMI Research | volume = 10 | issue = 1 | pages = 103 | date = September 2020 | pmid = 32910291 | pmc = 7483702 | doi = 10.1186/s13550-020-00689-z | doi-access = free }}</ref> Further studies evaluating the clinical use of <sup>18</sup>F-EF5 PET imaging in head and neck cancer are ongoing.
⚫ ==References==

⚫ == References ==
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