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<title>2-(2-Nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-[18F]pentafluoropropyl)-acetamide - Molecular Imaging and Contrast Agent Database (MICAD) - NCBI Bookshelf</title>
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<div class="pre-content"><div><div class="bk_prnt"><p class="small">NCBI Bookshelf. A service of the National Library of Medicine, National Institutes of Health.</p><p>Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. </p></div><div class="iconblock clearfix whole_rhythm no_top_margin bk_noprnt"><a class="img_link icnblk_img" title="Table of Contents Page" href="/books/n/micad/"><img class="source-thumb" src="/corehtml/pmc/pmcgifs/bookshelf/thumbs/th-micad-lrg.png" alt="Cover of Molecular Imaging and Contrast Agent Database (MICAD)" height="100px" width="80px" /></a><div class="icnblk_cntnt eight_col"><h2>Molecular Imaging and Contrast Agent Database (MICAD) [Internet].</h2><a data-jig="ncbitoggler" href="#__NBK23004_dtls__">Show details</a><div style="display:none" class="ui-widget" id="__NBK23004_dtls__"><div>Bethesda (MD): <a href="https://www.ncbi.nlm.nih.gov/" ref="pagearea=page-banner&targetsite=external&targetcat=link&targettype=publisher">National Center for Biotechnology Information (US)</a>; 2004-2013.</div></div><div class="half_rhythm"><ul class="inline_list"><li style="margin-right:1em"><a class="bk_cntns" href="/books/n/micad/">Contents</a></li></ul></div><div class="bk_noprnt"><form method="get" action="/books/n/micad/" id="bk_srch"><div class="bk_search"><label for="bk_term" class="offscreen_noflow">Search term</label><input type="text" title="Search this book" id="bk_term" name="term" value="" data-jig="ncbiclearbutton" /> <input type="submit" class="jig-ncbibutton" value="Search this book" submit="false" style="padding: 0.1em 0.4em;" /></div></form></div></div><div class="icnblk_cntnt two_col"><div class="pagination bk_noprnt"><a class="active page_link prev" href="/books/n/micad/NEFT18F/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/EF-mono/" title="Next page in this title">Next ></a></div></div></div></div></div>
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<div class="main-content lit-style" itemscope="itemscope" itemtype="http://schema.org/CreativeWork"><div class="meta-content fm-sec"><h1 id="_NBK23004_"><span class="title" itemprop="name">2-(2-Nitro-1<i>H</i>-imidazol-1-yl)-<i>N</i>-(2,2,3,3,3-[<sup>18</sup>F]pentafluoropropyl)-acetamide</span></h1><div itemprop="alternativeHeadline" class="subtitle whole_rhythm">[<sup>18</sup>F]EF5</div><p class="contrib-group"><span itemprop="author">The MICAD Research Team</span>.</p><p class="small">Created: <span itemprop="datePublished">November 8, 2005</span>; Last Update: <span itemprop="dateModified">December 31, 2005</span>.</p></div><div class="jig-ncbiinpagenav body-content whole_rhythm" data-jigconfig="allHeadingLevels: ['h2'],smoothScroll: false" itemprop="text"><div id="EF5.T1" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK23004/table/EF5.T1/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__EF5.T1_lrgtbl__"><table><tbody><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
|
||
<b>Chemical name:</b>
|
||
</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">2-(2-nitro-1<i>H</i>-imidazol-1-yl)-<i>N</i>-(2,2,3,3,3-[<sup>18</sup>F]pentafluoropropyl)-acetamide</td><td rowspan="9" colspan="1" style="text-align:left;vertical-align:middle;">
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||
<a href="https://pubchem.ncbi.nlm.nih.gov/substance/7978460" title="View this structure in PubChem" class="img_link" ref="pagearea=body&targetsite=entrez&targetcat=link&targettype=pubchem"><img src="https://pubchem.ncbi.nlm.nih.gov/image/imgsrv.fcgi?t=l&sid=7978460" alt="image 7978460 in the ncbi pubchem database" /></a>
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</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Abbreviated name:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">[<sup>18</sup>F]EF5</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Synonym:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">[<sup>18</sup>F]-2-(2-nitro-1<i>H</i>-imidazol-1-yl)-<i>N</i>-(2,2,3,3,3-[<sup>18</sup>F]pentafluoropropyl)-acetamide</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Agent Category:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Compound</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Target:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Hypoxic cells</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Target Category:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Intracellular reduction and binding</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Method of detection:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">PET</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Source of signal:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;"><sup>18</sup>F</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Activation:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">No</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Studies:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">
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<ul class="simple-list"><li id="A809" class="half_rhythm"><div>
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<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" />
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<i>In vitro</i>
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</div></li><li id="A810" class="half_rhythm"><div>
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<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" /> Rodents
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</div></li></ul>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Click on the above structure for additional information in <a href="http://pubchem.ncbi.nlm.nih.gov" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubChem</a>.</td></tr></tbody></table></div></div><div id="EF5.Background"><h2 id="_EF5_Background_">Background</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=18F%5BAll%20Fields%5D%20AND%20EF5%5BAll%20Fields%5D" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Hypoxia in malignant tumors is thought to be a major factor limiting the efficacy of chemotherapy and radiotherapy, and its accurate diagnosis is considered a very important and urgent problem to address. This has led to the search for and development of hypoxia-targeted imaging techniques and non-invasive markers of tumor hypoxia. Among those, <sup>18</sup>F-labeled nitroimidazoles - used in conjunction with positron emission tomography (PET) – offer a alternative that is less invasive and less prone to sampling errors than the Eppendorf (oxygen) electrode method (<a class="bk_pop" href="#EF5.EXTYLES.1">1</a>, <a class="bk_pop" href="#EF5.EXTYLES.2"> 2</a>).</p><p>Fluoromisonidazole (<a href="/books/n/micad/FMISO/"><u>[</u><sup><u>18</u></sup><u>F]FMISO</u></a>) is the nitroimidazole derivative most widely used with PET. Novel 2-nitroimidazoles, such as <sup>18</sup>F-labeled fluoroetanidazole (<a href="/books/n/micad/FETA/"><u>[</u><sup><u>18</u></sup><u>F]FETA</u></a>) (<a class="bk_pop" href="#EF5.EXTYLES.3">3</a>), fluoroerythronitroimidazole (<a href="/books/n/micad/FETNIM/"><u>[</u><sup><u>18</u></sup><u>F]FETNIM</u></a>) (<a class="bk_pop" href="#EF5.EXTYLES.4">4</a>), 4-bromo-1-(3-fluoropropyl)-2-nitroimidazole (<a href="/books/n/micad/BrFPN/"><u>4-Br[</u><sup><u>18</u></sup><u>F]FPN</u></a>) (<a class="bk_pop" href="#EF5.EXTYLES.5">5</a>), and 2-(2-nitroimidazol-1<i>H</i>-yl)-<i>N</i>-(3-fluoropropyl)acetamide (<a href="/books/n/micad/EF-mono/"><u>[</u><sup><u>18</u></sup><u>F]EF1</u></a>) (<a class="bk_pop" href="#EF5.EXTYLES.6">6</a>), are currently under investigation as PET markers for hypoxia.</p><p>The pentafluorinated molecule EF5 (2-(2-nitro-1<i>H</i>-imidazol-1-yl)-<i>N</i>-(2,2,3,3,3-pentafluoropropyl)-acetamide), previously used for measurement of hypoxia by immunohistochemistry (<a class="bk_pop" href="#EF5.EXTYLES.7">7</a>) and flow cytometry (<a class="bk_pop" href="#EF5.EXTYLES.8">8</a>), is currently being investigated as a PET agent for hypoxia. [<sup>18</sup>F]EF5 has the advantage of being more lipophilic than [<sup>18</sup>F]EF1 (octanol-water partition coefficient of 5.7 for [<sup>18</sup>F]EF5 <i>versus</i> 0.35 for [<sup>18</sup>F]EF1) because of its multiple fluorine atoms. [<sup>18</sup>F]EF5 can easily access all tissues, including those in the nervous system.</p><p>The oxygen-dependent metabolism of [<sup>18</sup>F]EF5 is an intracellular process consisting of a series of one-electron reductions. The nitro-radical anion produced in the first reduction step is very reactive toward oxygen, leaving no substrate for the second step of the reduction process. In contrast, a low-oxygen environment induces further reductive reactions that ultimately lead either to the formation of reactive products that can covalently bind to cell components or to charged species that diffuse slowly out of the tissues (<a class="bk_pop" href="#EF5.EXTYLES.1">1</a>). The reactive products observed during this multistep process include nitroso (2e<sup>-</sup>), hydroxylamine (4e<sup>-</sup>), and amine (6e<sup>-</sup>) derivatives. When fragmentation of the imidazole ring occurs, reactive portions of the molecule, such as glyoxal, bind to macromolecular components of cells in tissues and tumors (<a class="bk_pop" href="#EF5.EXTYLES.2">2</a>).</p></div><div id="EF5.Synthesis"><h2 id="_EF5_Synthesis_">Synthesis</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=18F%5BAll%20Fields%5D%20AND%20EF5%5BAll%20Fields%5D%20AND%20synthesis%5BAll%20Fields%5D" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>[<sup>18</sup>F]EF5 can be produced by direct fluorination of the precursor 2-(2-nitro-1<i>H</i>-imidazol-1-yl)-<i>N</i>-(2,3,3-trifluoroallyl)-acetamide by [<sup>18</sup>F]F<sub>2</sub> in trifluoroacetic acid, as described by Dolbier et al. (<a class="bk_pop" href="#EF5.EXTYLES.9">9</a>). The yield obtained by this method is greater than 10%.</p><p>Synthesis details have also been reported by Ziemer et al. (<a class="bk_pop" href="#EF5.EXTYLES.10">10</a>). Their described procedure also involves adding fluorine gas across the double bond of an allyl precursor in trifluoroacetic acid at 0 °C. After evaporation under vacuum, the products are purified by high-performance liquid chromatography (HPLC). After dissolution in physiologic saline, the purified radioactive drug is added to unlabeled EF5. The maximum specific activity for [<sup>18</sup>F]EF5 synthesis is about 37 × 10<sup>3</sup> MBq (1,000 mCi)/mmol (when using 7400 MBq (200 mCi) of radioactivity in 70 µmol of fluorine carrier, and assuming a 30% labeling efficiency).</p></div><div id="EF5.In_Vitro_Studies_Tes"><h2 id="_EF5_In_Vitro_Studies_Tes_"><i>In Vitro</i> Studies: Testing in Cells and Tissues</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%2818F%29EF5%20AND%20PET%20AND%20in%20vitro" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No <i>in vitro</i> study using the PET agent [<sup>18</sup>F]EF5 has been reported in the literature to date. Nevertheless, data on the distribution and levels of EF5 binding using fluorescence immunohistochemical techniques have been reported for human head-and-neck and cervical squamous cancer cells (<a class="bk_pop" href="#EF5.EXTYLES.11">11</a>). In those studies, the maximum rate of <i>in situ</i> binding varied by a factor of 6.7 between the lowest (24.8) and the highest (160.3) on an absolute fluorescence scale. Intratumoral heterogeneity was observed for tumors with high binding regions. In contrast, this heterogeneity was minimal for tumors with minimal binding.</p></div><div id="EF5.Animal_Studies"><h2 id="_EF5_Animal_Studies_">Animal Studies</h2><div id="EF5.Rodents"><h3>Rodents</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%2818F%29EF5%20AND%20rodentia%5BMeSH%5D" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Biodistribution studies using male Fischer rats bearing Morris 7777 (Q7) tumors and 9L glioma were performed by Ziemer et al. (<a class="bk_pop" href="#EF5.EXTYLES.10">10</a>). The rats were injected with approximately 50-100 μCi of [<sup>18</sup>F]EF5 and 100 μmol/kg of nonradioactive EF5 (used as added carrier). Images were taken at 10, 60, 120, and 180 min post injection through the femoral vein. [<sup>18</sup>F]EF5 was shown to be distributed fairly uniformly, with activity uptake increasing over time in the kidneys and gastrointestinal (GI) tract. This increase suggests that [<sup>18</sup>F]EF5 is excreted via the urinary system, consistent with prior research studies of EF5 in rodents (<a class="bk_pop" href="#EF5.EXTYLES.12">12</a>). In contrast, the activity in the liver appeared to be roughly constant and decreasing slowly over time.</p><p>At 60 min post injection, the values for the ratio of activity in organs to activity in muscle were as follows: 2.0 (liver), 2.5 (kidney), and 2.7 (GI tract). At 120 min post injection, those ratios were 1.9 (liver), 2.8 (kidney), and 3.9 (GI tract) (as reported in figure 2 of Ziemer et al. (<a class="bk_pop" href="#EF5.EXTYLES.10">10</a>)). For Q7 tumor -bearing rats, the following tumor/muscle activity ratios (TMR) were obtained: 1.5 (kidney), 1.4 (liver), and 1.3 (GI tract) at 60 min post injection; and 1.2 (kidney), 1.7 (liver), and 1.6 (GI tract) at 120 min post injection (as reported in figure 3 of Ziemer et al. (<a class="bk_pop" href="#EF5.EXTYLES.10">10</a>)).</p><p>Additional measurements of TMR values based on gamma counts led to consistently higher values than those obtained with PET imaging. As an example, the TMR value obtained for a Q7 tumor of size 14 × 14 × 14 = 2,744 mm<sup>3</sup> was 1.73 with PET imaging but 2.43 when gamma-counted. This difference was thought to be likely due to the small tumor size and the partial volume effect.</p></div><div id="EF5.Other_NonPrimate_Mam"><h3>Other Non-Primate Mammals</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%2818F%29EF5%20AND%20%28dog%20OR%20pig%20OR%20sheep%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div><div id="EF5.NonHuman_Primates"><h3>Non-Human Primates</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%2818F%29EF5%20AND%20%28primate%20NOT%20human%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div></div><div id="EF5.Human_Studies"><h2 id="_EF5_Human_Studies_">Human Studies</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%2818F%29EF5%20AND%20human" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication reporting on [<sup>18</sup>F]EF5 as a PET agent in human studies is currently available. Nevertheless, EF5 is approved for use in humans and is currently in phase II clinical trials using antibody techniques for the detection of hypoxic cells (<a class="bk_pop" href="#EF5.EXTYLES.13">13</a>).</p></div><div id="EF5.references"><h2 id="_EF5_references_">References</h2><dl class="temp-labeled-list"><dt>1.</dt><dd><div class="bk_ref" id="EF5.EXTYLES.1">Nunn A , Linder K , Strauss HW . Nitroimidazoles and imaging hypoxia. <span><span class="ref-journal">Eur J Nucl Med. </span>1995;<span class="ref-vol">22</span>(3):265–280.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/7789400" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 7789400</span></a>]</div></dd><dt>2.</dt><dd><div class="bk_ref" id="EF5.EXTYLES.2">Hodgkiss RJ . Use of 2-nitroimidazoles as bioreductive markers for tumour hypoxia. <span><span class="ref-journal">Anticancer Drug Des. </span>1998;<span class="ref-vol">13</span>(6):687–702.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/9755725" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 9755725</span></a>]</div></dd><dt>3.</dt><dd><div class="bk_ref" id="EF5.EXTYLES.3">Rasey JS , Hofstrand PD , Chin LK , Tewson TJ . Characterization of [18F]fluoroetanidazole, a new radiopharmaceutical for detecting tumor hypoxia. <span><span class="ref-journal">J Nucl Med. </span>1999;<span class="ref-vol">40</span>(6):1072–1079.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/10452326" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 10452326</span></a>]</div></dd><dt>4.</dt><dd><div class="bk_ref" id="EF5.EXTYLES.4">Yang DJ , Wallace S , Cherif A , Li C , Gretzer MB , Kim EE , Podoloff DA . Development of F-18-labeled fluoroerythronitroimidazole as a PET agent for imaging tumor hypoxia. <span><span class="ref-journal">Radiology. </span>1995;<span class="ref-vol">194</span>(3):795–800.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/7862981" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 7862981</span></a>]</div></dd><dt>5.</dt><dd><div class="bk_ref" id="EF5.EXTYLES.5">Yamamoto F , Aoki M , Furusawa Y , Ando K , Kuwabara Y , Masuda K , Sasaki S , Maeda M . Synthesis and evaluation of 4-bromo-1-(3-[18F]fluoropropyl)-2-nitroimidazole with a low energy LUMO orbital designed as brain hypoxia-targeting imaging agent. <span><span class="ref-journal">Biol Pharm Bull. </span>2002;<span class="ref-vol">25</span>(5):616–621.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12033502" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12033502</span></a>]</div></dd><dt>6.</dt><dd><div class="bk_ref" id="EF5.EXTYLES.6">Kachur AV , Dolbier WR , Evans SM , Shiue CY , Shiue GG , Skov KA , Baird IR , James BR , Li AR , Roche A , Koch CJ . Synthesis of new hypoxia markers EF1 and [18F]-EF1. <span><span class="ref-journal">Appl Radiat Isot. </span>1999;<span class="ref-vol">51</span>(6):643–650.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/10581679" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 10581679</span></a>]</div></dd><dt>7.</dt><dd><div class="bk_ref" id="EF5.EXTYLES.7">Evans SM , Joiner B , Jenkins WT , Laughlin KM , Lord EM , Koch CJ . Identification of hypoxia in cells and tissues of epigastric 9L rat glioma using EF5. <span><span class="ref-journal">Br J Cancer. </span>1995;<span class="ref-vol">72</span>(4):875–882.</span> [<a href="/pmc/articles/PMC2034029/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC2034029</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/7547234" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 7547234</span></a>]</div></dd><dt>8.</dt><dd><div class="bk_ref" id="EF5.EXTYLES.8">Evans SM , Jenkins WT , Joiner B , Lord EM , Koch CJ . 2-Nitroimidazole (EF5) binding predicts radiation resistance in individual 9L s.c. tumors. <span><span class="ref-journal">Cancer Res. </span>1996;<span class="ref-vol">56</span>(2):405–411.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/8542599" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 8542599</span></a>]</div></dd><dt>9.</dt><dd><div class="bk_ref" id="EF5.EXTYLES.9">Dolbier WR , Li AR , Koch CJ , Shiue CY , Kachur AV . [18F]-EF5, a marker for PET detection of hypoxia: synthesis of precursor and a new fluorination procedure. <span><span class="ref-journal">Appl Radiat Isot. </span>2001;<span class="ref-vol">54</span>(1):73–80.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/11144255" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 11144255</span></a>]</div></dd><dt>10.</dt><dd><div class="bk_ref" id="EF5.EXTYLES.10">Ziemer LS , Evans SM , Kachur AV , Shuman AL , Cardi CA , Jenkins WT , Karp JS , Alavi A , Dolbier WR , Koch CJ . Noninvasive imaging of tumor hypoxia in rats using the 2-nitroimidazole 18F-EF5. <span><span class="ref-journal">Eur J Nucl Med Mol Imaging. </span>2003;<span class="ref-vol">30</span>(2):259–266.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12552344" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12552344</span></a>]</div></dd><dt>11.</dt><dd><div class="bk_ref" id="EF5.EXTYLES.11">Evans SM , Hahn S , Pook DR , Jenkins WT , Chalian AA , Zhang P , Stevens C , Weber R , Weinstein G , Benjamin I , Mirza N , Morgan M , Rubin S , McKenna WG , Lord EM , Koch CJ . Detection of hypoxia in human squamous cell carcinoma by EF5 binding. <span><span class="ref-journal">Cancer Res. </span>2000;<span class="ref-vol">60</span>(7):2018–2024.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/10766193" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 10766193</span></a>]</div></dd><dt>12.</dt><dd><div class="bk_ref" id="EF5.EXTYLES.12">Laughlin KM , Evans SM , Jenkins WT , Tracy M , Chan CY , Lord EM , Koch CJ . Biodistribution of the nitroimidazole EF5 (2-[2-nitro-1H-imidazol-1-yl]-N-(2,2,3,3,3-pentafluoropropyl) acetamide) in mice bearing subcutaneous EMT6 tumors. <span><span class="ref-journal">J Pharmacol Exp Ther. </span>1996;<span class="ref-vol">277</span>(2):1049–1057.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/8627516" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 8627516</span></a>]</div></dd><dt>13.</dt><dd><div class="bk_ref" id="EF5.EXTYLES.13">Koch CJ , Hahn SM , Rockwell K , Covey JM , McKenna WG , Evans SM . Pharmacokinetics of EF5 [2-(2-nitro-1-H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl) acetamide] in human patients: implications for hypoxia measurements in vivo by 2-nitroimidazoles. <span><span class="ref-journal">Cancer Chemother Pharmacol. </span>2001;<span class="ref-vol">48</span>(3):177–187.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/11592338" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 11592338</span></a>]</div></dd></dl></div><div id="bk_toc_contnr"></div></div></div>
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<div class="post-content"><div><div class="half_rhythm"><a href="/books/about/copyright/">Copyright Notice</a></div><div class="small"><span class="label">Bookshelf ID: NBK23004</span><span class="label">PMID: <a href="https://pubmed.ncbi.nlm.nih.gov/20641211" title="PubMed record of this page" ref="pagearea=meta&targetsite=entrez&targetcat=link&targettype=pubmed">20641211</a></span></div><div style="margin-top:2em" class="bk_noprnt"><a class="bk_cntns" href="/books/n/micad/">Contents</a><div class="pagination bk_noprnt"><a class="active page_link prev" href="/books/n/micad/NEFT18F/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/EF-mono/" title="Next page in this title">Next ></a></div></div></div></div>
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