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<title>4-(2´-Methoxyphenyl)-1-[2´-(N-2´´-1,3 pyrimidino)-p-[18F]fluorobenzamido]ethylpiperazine - Molecular Imaging and Contrast Agent Database (MICAD) - NCBI Bookshelf</title>
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<meta name="robots" content="INDEX,FOLLOW,NOARCHIVE" /><meta name="citation_inbook_title" content="Molecular Imaging and Contrast Agent Database (MICAD) [Internet]" /><meta name="citation_title" content="4-(2´-Methoxyphenyl)-1-[2´-(N-2´´-1,3 pyrimidino)-p-[18F]fluorobenzamido]ethylpiperazine" /><meta name="citation_publisher" content="National Center for Biotechnology Information (US)" /><meta name="citation_date" content="2008/06/30" /><meta name="citation_author" content="Kenneth T. Cheng" /><meta name="citation_pmid" content="20641340" /><meta name="citation_fulltext_html_url" content="https://www.ncbi.nlm.nih.gov/books/NBK23137/" /><link rel="schema.DC" href="http://purl.org/DC/elements/1.0/" /><meta name="DC.Title" content="4-(2´-Methoxyphenyl)-1-[2´-(N-2´´-1,3 pyrimidino)-p-[18F]fluorobenzamido]ethylpiperazine" /><meta name="DC.Type" content="Text" /><meta name="DC.Publisher" content="National Center for Biotechnology Information (US)" /><meta name="DC.Contributor" content="Kenneth T. Cheng" /><meta name="DC.Date" content="2008/06/30" /><meta name="DC.Identifier" content="https://www.ncbi.nlm.nih.gov/books/NBK23137/" /><meta name="description" content="4-(2´-Methoxyphenyl)-1-[2´-(N-2´´-1,3 pyrimidino)-p-[18F]fluorobenzamido]ethylpiperazine ([18F]FPWAY) is a radioligand developed for positron emission tomography (PET) imaging of serotonin-1A (5-HT1A) receptors in the central nervous system (1, 2). It is a selective 5-HT1A antagonist labeled with 18F, a positron emitter with a physical t½ of 109.7 min (3, 4)." /><meta name="og:title" content="4-(2´-Methoxyphenyl)-1-[2´-(N-2´´-1,3 pyrimidino)-p-[18F]fluorobenzamido]ethylpiperazine" /><meta name="og:type" content="book" /><meta name="og:description" content="4-(2´-Methoxyphenyl)-1-[2´-(N-2´´-1,3 pyrimidino)-p-[18F]fluorobenzamido]ethylpiperazine ([18F]FPWAY) is a radioligand developed for positron emission tomography (PET) imaging of serotonin-1A (5-HT1A) receptors in the central nervous system (1, 2). It is a selective 5-HT1A antagonist labeled with 18F, a positron emitter with a physical t½ of 109.7 min (3, 4)." /><meta name="og:url" content="https://www.ncbi.nlm.nih.gov/books/NBK23137/" /><meta name="og:site_name" content="NCBI Bookshelf" /><meta name="og:image" content="https://www.ncbi.nlm.nih.gov/corehtml/pmc/pmcgifs/bookshelf/thumbs/th-micad-lrg.png" /><meta name="twitter:card" content="summary" /><meta name="twitter:site" content="@ncbibooks" /><meta name="bk-non-canon-loc" content="/books/n/micad/FPWAY18F/" /><link rel="canonical" href="https://www.ncbi.nlm.nih.gov/books/NBK23137/" /><link rel="stylesheet" href="/corehtml/pmc/css/figpopup.css" type="text/css" media="screen" /><link rel="stylesheet" href="/corehtml/pmc/css/bookshelf/2.26/css/books.min.css" type="text/css" /><link rel="stylesheet" href="/corehtml/pmc/css/bookshelf/2.26/css/books_print.min.css" type="text/css" media="print" /><style type="text/css">p a.figpopup{display:inline !important} .bk_tt {font-family: monospace} .first-line-outdent .bk_ref {display: inline} .body-content h2, .body-content .h2 {border-bottom: 1px solid #97B0C8} .body-content h2.inline {border-bottom: none} a.page-toc-label , .jig-ncbismoothscroll a {text-decoration:none;border:0 !important} .temp-labeled-list .graphic {display:inline-block !important} .temp-labeled-list img{width:100%}</style><script type="text/javascript" src="/corehtml/pmc/js/jquery.hoverIntent.min.js"> </script><script type="text/javascript" src="/corehtml/pmc/js/common.min.js?_=3.18"> </script><script type="text/javascript" src="/corehtml/pmc/js/large-obj-scrollbars.min.js"> </script><script type="text/javascript">window.name="mainwindow";</script><script type="text/javascript" src="/corehtml/pmc/js/bookshelf/2.26/book-toc.min.js"> </script><script type="text/javascript" src="/corehtml/pmc/js/bookshelf/2.26/books.min.js"> </script><meta name="book-collection" content="NONE" />
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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="#__NBK23137_dtls__">Show details</a><div style="display:none" class="ui-widget" id="__NBK23137_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/FES-M-4F-18F/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/p-MPPF18F/" 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="_NBK23137_"><span class="title" itemprop="name">4-(2´-Methoxyphenyl)-1-[2´-(<i>N</i>-2´´-1,3 pyrimidino)-<i>p</i>-[<sup>18</sup>F]fluorobenzamido]ethylpiperazine</span></h1><div itemprop="alternativeHeadline" class="subtitle whole_rhythm">[<sup>18</sup>F]FPWAY</div><p class="contrib-group"><span itemprop="author">Kenneth T. Cheng</span>, PhD.</p><a data-jig="ncbitoggler" href="#__NBK23137_ai__" style="border:0;text-decoration:none">Author Information and Affiliations</a><div style="display:none" class="ui-widget" id="__NBK23137_ai__"><div class="contrib half_rhythm"><span itemprop="author">Kenneth T. Cheng</span>, PhD<div class="affiliation small">
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National Center for Biotechnology Information, NLM, NIH, Bethesda, MD,
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<span class="before-email-separator"></span><span class="email-label">Email: </span><a href="mailto:dev@null" data-email="vog.hin.mln.ibcn@dacim" class="oemail">vog.hin.mln.ibcn@dacim</a>
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</div></div></div><p class="small">Created: <span itemprop="datePublished">February 1, 2005</span>; Last Update: <span itemprop="dateModified">June 30, 2008</span>.</p></div><div class="jig-ncbiinpagenav body-content whole_rhythm" data-jigconfig="allHeadingLevels: ['h2'],smoothScroll: false" itemprop="text"><div id="FPWAY18F.T1" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK23137/table/FPWAY18F.T1/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__FPWAY18F.T1_lrgtbl__"><table><tbody><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Chemical name:</b>
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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">4-(2´-Methoxyphenyl)-1-[2´-(<i>N</i>-2´´-1,3 pyrimidino)-<i>p</i>-[<sup>18</sup>F]fluorobenzamido]ethylpiperazine</td><td rowspan="9" colspan="1" style="text-align:left;vertical-align:middle;"></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]FPWAY</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]FBWAY 1,3 N<br />4-[<sup>18</sup>F]-Fluoro-<i>N</i>-{2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl}-<i>N</i>-(2-pyrimidinyl)benzamide</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;">5-HT<sub>1A</sub> receptors</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;">Receptor-ligand 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;">Positron emission tomography (PET)</td></tr><tr><td rowspan="1" colspan="1" style="text-align:right;vertical-align:top;">
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<b>Source of signal/contrast:</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 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></ul>
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<ul class="simple-list"><li 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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<ul class="simple-list"><li class="half_rhythm"><div>
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<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" /> Non-primate non-rodent mammals
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</div></li></ul>
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<ul class="simple-list"><li class="half_rhythm"><div>
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<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" /> Non-human primates
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</div></li></ul>
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<ul class="simple-list"><li class="half_rhythm"><div>
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<img alt="Checkbox" src="/corehtml/pmc/css/bookshelf/2.26/img/studies.checkbox.png" /> Humans
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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="FPWAY18F.Background"><h2 id="_FPWAY18F_Background_">Background</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=FBWAY%201%2C3N%20OR%20FPWAY" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>4-(2´-Methoxyphenyl)-1-[2´-(<i>N</i>-2´´-1,3 pyrimidino)-<i>p</i>-[<sup>18</sup>F]fluorobenzamido]ethylpiperazine ([<sup>18</sup>F]FPWAY) is a radioligand developed for positron emission tomography (PET) imaging of serotonin-1A (5-HT<sub>1A</sub>) receptors in the central nervous system (<a class="bk_pop" href="#FPWAY18F.REF.1">1</a>, <a class="bk_pop" href="#FPWAY18F.REF.2">2</a>). It is a selective 5-HT<sub>1A</sub> antagonist labeled with <sup>18</sup>F, a positron emitter with a physical <i>t</i><sub>½</sub> of 109.7 min (<a class="bk_pop" href="#FPWAY18F.REF.3">3</a>, <a class="bk_pop" href="#FPWAY18F.REF.4">4</a>).</p><p>The serotonin (5-hydroxytryptamine (5-HT)) neurotransmission system consists mainly of neurons in the brainstem, with nerve tracts extending from these neurons to many areas of the brain and spinal cord. During firing, the neurons release 5-HT, a neurotransmitter that is involved in the modulation of various important physiologic functions and behavior, such as thermoregulation, cardiovascular function, aggressive and sexual behavior, mood, appetite, and the sleep–wake cycle. The effects of 5-HT are mediated by as many as seven classes of receptor populations (5-HT<sub>1</sub> to 5-HT<sub>7</sub>), many of which also contain several subtypes. There are five receptor subtypes within the G protein-coupled 5-HT<sub>1</sub> receptor family, with the 5-HT<sub>1A</sub> subtype located primarily in the limbic forebrain (the hippocampus, entorhinal cortex and septum). 5-HT<sub>1A</sub> receptors appear to function both as presynaptic (somatodendritic) autoreceptors in the raphe nuclei and as postsynaptic receptors in the terminal fields. This receptor subtype is involved in the modulation of emotion and the function of the hypothalamus, and is implicated in the pathogenesis of anxiety, depression, hallucinogenic behavior, motion sickness, dementia, schizophrenia, and eating disorders. A radioligand that can be used to assess the <i>in vivo</i> densities of 5-HT<sub>1A</sub> receptors and their changes may facilitate investigation of the relationship of these receptors to various neuropsychiatric diseases and aid in the design of novel drugs for their treatment.</p><p>Many psychiatric drugs modulate serotonergic transmission or specifically target the 5-HT<sub>1A</sub> receptors. Various compounds have been radiolabeled for visualization and quantification of these receptors. WAY 100635 was developed as a highly selective, silent antagonist (possessing no intrinsic agonist activity) of 5HT<sub>1A</sub> receptors at both pre- and postsynaptic sites. <a href="/books/n/micad/Carbonyl11C-WAY/">WAY 100635</a> radiolabeled with <sup>11</sup>C at the carbonyl position is an effective radioligand but it is rapidly cleared and metabolized. The short <i>t</i><sub>½</sub> of <sup>11</sup>C also presents some challenges in clinical application of the radiotracer. A radioligand with slower metabolism and labeled with a longer-lived radioisotope would be a better agent for quantitative PET studies. A number of fluorinated derivatives of WAY 100635 have been developed. In 2000, Lang et al. (<a class="bk_pop" href="#FPWAY18F.REF.5">5</a>) synthesized [<sup>18</sup>F]FPWAY with labeling at the carboxamide moiety to minimize metabolites that cross the blood-brain barrier (BBB). [<sup>18</sup>F]FPWAY appears to be an intermediate-affinity antagonist of the 5-HT<sub>1A</sub> receptors and may be more sensitive to transient changes in endogenous 5-HT<sub>1A</sub> levels than high-affinity analogs (<a class="bk_pop" href="#FPWAY18F.REF.6">6</a>). In this WAY 100635 analog, the pyridine ring is replaced by pyrimidine and the cyclohexane ring is replaced by fluorobenzyl. With <sup>18</sup>F in the 4 position of the benzamide, [<sup>18</sup>F]FPWAY is a very different compound from another WAY 100635 analog with a similar abbreviation, <a href="/books/n/micad/F6PWAY18F/">[<sup>18</sup>F]6FPWAY</a>, which was synthesized by Marchais et al. (<a class="bk_pop" href="#FPWAY18F.REF.7">7</a>). [<sup>18</sup>F]6FPWAY contains a N-pyridine with <sup>18</sup>F in the 6 position of the pyridine moiety.</p></div><div id="FPWAY18F.Synthesis"><h2 id="_FPWAY18F_Synthesis_">Synthesis</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%28FBWAY%201%2C3N%20OR%20FPWAY%29%20AND%20synthesis" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Lang et al. (<a class="bk_pop" href="#FPWAY18F.REF.5">5</a>, <a class="bk_pop" href="#FPWAY18F.REF.8">8</a>) first reported the synthesis of FPWAY based on FBWAY (or <i>p</i>-MPPF). FPWAY was synthesized as an FBWAY analog (FBWAY 1,3 N) with a 1,3 pyrimidine substituent. FBWAY was prepared by reacting WAY 100634 with the corresponding acid chloride in methylene chloride. Radiolabeling involved labeling the 4-trimethylamino precursor with <sup>18</sup>F to produce the radiolabeled 4-fluorobenzoyl chloride. The product was purified by high-performance liquid chromatography (HPLC). The radiochemical yield ranged between 10 and 20%, and the total synthesis time was between 80 and 90 min. The specific activity was 37,000 GBq (1,000 Ci)/mmol at the end of bombardment (EOB).</p><p>Ma et al. (<a class="bk_pop" href="#FPWAY18F.REF.9">9</a>) described a similar synthesis of FPWAY from {2-[4-(2-methoxyphenyl)-1-piperazinyl]-ethyl}-<i>N</i>-(2-pyrimidinyl)amine which was prepared from 2-[4-(2-methoxyphenyl)-1-piperazinyl]ethylamine (obtained commercially) by reaction with 2-chloropyrimidine in ethanol and sodium carbonate overnight. The yield was 79%. The final compound was reacted with 4-fluorobenzoyl chloride in triethylamine and 1,2-dichloroethane overnight to give a final yield of 96%. This precursor was reacted with [<sup>18</sup>F]− Kryptofix in dimethyl sulfoxide and heated in a microwave oven for 2 min. The product was purified by reverse-phase HPLC and a C-18 Sep-Pak to give a final yield of 25-35% EOB and radiochemical purity of 99.0%.</p></div><div id="FPWAY18F.In_Vitro_Studies_Tes"><h2 id="_FPWAY18F_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=%28FBWAY%201%2C3N%20OR%20FPWAY%29%20AND%20in%20vitro%20studies" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p><i>In vitro</i> affinity of [<sup>18</sup>F]FPWAY was studied by Lang et al. (<a class="bk_pop" href="#FPWAY18F.REF.5">5</a>), and the inhibition constant, <i>K</i><sub>i</sub>, was determined to be <1 nM against [<sup>18</sup>H]8-hydroxy-2-dipropylaminotetralin ([<sup>3</sup>H]8-OH-DPAT) binding to a cloned cell line containing 5-HT<sub>1A</sub> receptors. This was relatively weak when compared with other high affinity WAY analogs (MeFWAY and Trans-FCWAY). The antagonist inhibition concentration (IC<sub>50</sub>)was determined to be 340 nM based on the compound’s ability to inhibit relaxation induced by 0.3 µM 8-OH-DPAT. On the basis of the compound’s ability to relax guinea pig field-stimulated ileum, the authors concluded that [<sup>18</sup>F]FPWAY showed no agonist activity.</p><p><i>In vitro</i> metabolism studies of FPWAY and [<sup>18</sup>F]FPWAY were performed by Ma et al. (<a class="bk_pop" href="#FPWAY18F.REF.9">9</a>) in cryopreserved hepatocytes of rat and human liver tissue. Metabolites were identified by liquid chromatography−tandem mass spectrometry. In rat hepatocytes, aromatic-ring oxidation was the major metabolism pathway for FPWAY, but there was also amide hydrolysis. Amide hydrolysis products were the major metabolites of FPWAY in human hepatocytes, and the metabolic rate appeared to be higher than for other fluorinated analogs of WAY 100635 (FBWAY and MeFBWAY). The study suggested that the pyrimidyl for pyridyl substitution in FPWAY made the amide more labile to metabolic hydrolysis. In a [<sup>18</sup>F]FPWAY imaging study using monkey blood, it was shown that pure [<sup>18</sup>F]FPWAY could be readily extracted by an organic phase (hexane−etyhl acetate 4:1) from its metabolites in a basic aqueous phase (125 mM KCl-NaOH, pH 12.5). This simplified the determination of the input function.</p></div><div id="FPWAY18F.Animal_Studies"><h2 id="_FPWAY18F_Animal_Studies_">Animal Studies</h2><div id="FPWAY18F.Rodents"><h3>Rodents</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%28FBWAY%201%2C3N%20OR%20FPWAY%29%20AND%20rodentia" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Lang et al. (<a class="bk_pop" href="#FPWAY18F.REF.5">5</a>) studied the clearance of [<sup>18</sup>F]FPWAY from the rat brain by injecting the compound into rats. [<sup>18</sup>F]FPWAY appeared to have a two-component net efflux curve. Brain distribution and binding saturability were also determined in rats. The differential uptake ratios (DURs, calculated as % of injected dose x animal weight (g)/100) of [<sup>18</sup>F]FPWAY at 30 min were 0.403 ± 0.056 (<i>n</i> ≥ 4), 0.918 ± 0.107, and 0.141 ± 0.019 for the cortex, hippocampus, and cerebellum, respectively. When 200 nmol of WAY 100635 was co-injected along with [<sup>18</sup>F]FPWAY, the DURs decreased to 0.153 ± 0.040, 0.145 ± 0.040, and 0.131 ± 0.033 for the cortex, hippocampus, and cerebellum, respectively. The hippocampus/cerebellum ratios were 5.5 and 0.1 with and without 200 nM WAY 100635, respectively. The kinetic sensitivity (change in DUR per change in receptor concentration) of this compound appeared to be intermediate between FCWAY and FBWAY.</p><p>Jagoda et al. (<a class="bk_pop" href="#FPWAY18F.REF.10">10</a>) conducted autoradiography, biodistribution, and metabolite studies of [<sup>18</sup>F]FPWAY and other analogs ([<sup>18</sup>F]FCWAY and [<sup>18</sup>F]FBWAY) in rats and mice. The DURs (dose = 1850 kBq (50 µCi); <i>n</i> = 5) in rats at 30 min after injection for the hippocampus and cerebellum were 0.92 ± 0.11 and 0.14 ± 0.02, respectively. Their (hippocampus DUR/cerebellum DUR) − 1 ratio ((H/Cb) − 1) was 5.5. With the administration of WAY 100635 (200 nmol), the DURs for the hippocampus and cerebellum decreased to 0.14 ± 0.04 and 0.13 ± 0.03, respectively. The specific binding ratios (hippocampus/cerebellum) were 9, 4.6, and 0.1 for the mice of wildtype, heterozygotes, and receptor knockout mice, respectively. This showed that [<sup>18</sup>F]FPWAY bound specifically to the 5-HT<sub>1A</sub> receptors and was sensitive to changes in receptor density. Similar differences in localization patterns were observed in [<sup>18</sup>F]FPWAY autoradiography studies. The results from the blocking studies with WAY 100635 in rat and mouse brains were consistent with the fact that [<sup>18</sup>F]FPWAY possesses a lower 5HT<sub>1A</sub> receptor affinity than do high-affinity analogs. [<sup>18</sup>F]FPWAY regional bindings in the brains of “awake” mice showed no significant changes in response to treatments with paroxetine (a selective serotonin reuptake inhibitor) or fenfluramine (a serotonin transporter substrate and releasing agent). With use of the “chase” paradigm, a consistent pattern of changes of [<sup>18</sup>F]FPWAY regional brain binding in awake rats treated with fenfluramine or paroxetine was not observed. Urethane-anesthetized rats treated with fenfluramine also showed no significant changes in the specific binding ratios in the hippocampus. The study suggested that the <i>in vivo</i> serotonin system is tightly controlled so that changes in radioligand affinity alone might not produce significant changes in detection sensitivity for changes in endogenous 5-HT.</p></div><div id="FPWAY18F.Other_NonPrimate_Mam"><h3>Other Non-Primate Mammals</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%28FBWAY%201%2C3N%20OR%20FPWAY%29%20AND%20%28dog%20OR%20rabbit%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="FPWAY18F.NonHuman_Primates"><h3>Non-Human Primates</h3><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%28FBWAY%201%2C3N%20OR%20FPWAY%29%20AND%20%28primate%20NOT%20human%29" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Carson et al. (<a class="bk_pop" href="#FPWAY18F.REF.11">11</a>) studied the brain penetration of [<sup>18</sup>F]fluorobenzoic acid ([<sup>18</sup>F]FB), a major acid metabolite of [<sup>18</sup>F]FPWAY, in rhesus monkeys. PET imaging showed that [<sup>18</sup>F]FB crossed the BBB, but it did not have a significant effect on 5-HT<sub>1A</sub> receptor quantification of [<sup>18</sup>F]FPWAY. HPLC analysis of arterial blood samples also showed no metabolites when [<sup>18</sup>F]FB was injected.</p><p>Giovacchini et al. (<a class="bk_pop" href="#FPWAY18F.REF.6">6</a>) used PET imaging (10-40 min after injection) in rhesus monkeys to assess the response of [<sup>18</sup>F]FPWAY to dynamic <i>in vivo</i> changes in serotonergic neurotransmission caused by systemic administration of paroxetine. A dose of 259-518 MBq (7-14 mCi) of [<sup>18</sup>F]FPWAY (specific activity was 111 GBq (3 Ci/µmol) at time of administration), TOA) was given with a bolus-plus-infusion technique to achieve constant radioactivity in all brain regions. The distribution of radioactivity in the brain was consistent with the known concentrations of 5-HT<sub>1A</sub> receptors. The baseline binding potential (BP<sub>2</sub>) values of the raphe region, anterior cingulated, and frontal lobe were 0.53 ± 0.06, 1.90 ± 0.08, and 0.93 ± 0.08, respectively. Paroxetine administration (5 mg/kg) caused decreases of raphe BP<sub>2</sub>s ranging from 8 ± 6% during the first 30 min period to 27 ± 10% during the sixth 30-min period (180-240 min). On the other hand, cortical BP<sub>2</sub> values increased by 7 ± 3% during the first 30-min period and by 13 ± 5% during the second 30-min period, and then progressively decreased. The study suggested that dynamic changes in 5-HT<sub>1A</sub> neurotransmission could be quantified by [<sup>18</sup>F]FPWAY PET imaging.</p></div></div><div id="FPWAY18F.Human_Studies"><h2 id="_FPWAY18F_Human_Studies_">Human Studies</h2><p>[<a href="/entrez/query.fcgi?cmd=PureSearch&db=pubmed&details_term=%28FBWAY%201%2C3N%20OR%20FPWAY%29%20AND%20human" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div><div id="FPWAY18F.NIH_Support"><h2 id="_FPWAY18F_NIH_Support_">NIH Support</h2><p>NIH Intramural Support. NIH Contract NO1MH2003.</p></div><div id="FPWAY18F.references"><h2 id="_FPWAY18F_references_">References</h2><dl class="temp-labeled-list"><dt>1.</dt><dd><div class="bk_ref" id="FPWAY18F.REF.1">Passchier J. , van Waarde A. Visualisation of serotonin-1A (5-HT1A) receptors in the central nervous system. <span><span class="ref-journal">Eur J Nucl Med. </span>2001;<span class="ref-vol">
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<strong>28</strong>
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</span>(1):113–29.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/11202445" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 11202445</span></a>]</div></dd><dt>2.</dt><dd><div class="bk_ref" id="FPWAY18F.REF.2">McCarron J.A. , Pike V.W. , Halldin C. , Sandell J. , Sovago J. , Gulyas B. , Cselenyi Z. , Wikstrom H.V. , Marchais-Oberwinkler S. , Nowicki B. , Dolle F. , Farde L. The pyridinyl-6 position of WAY-100635 as a site for radiofluorination--effect on 5-HT1A receptor radioligand behavior in vivo. <span><span class="ref-journal">Mol Imaging Biol. </span>2004;<span class="ref-vol">
|
||
<strong>6</strong>
|
||
</span>(1):17–26.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15018825" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15018825</span></a>]</div></dd><dt>3.</dt><dd><div class="bk_ref" id="FPWAY18F.REF.3">Bantick R.A. , Rabiner E.A. , Hirani E. , de Vries M.H. , Hume S.P. , Grasby P.M. Occupancy of agonist drugs at the 5-HT1A receptor. <span><span class="ref-journal">Neuropsychopharmacology. </span>2004;<span class="ref-vol">
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||
<strong>29</strong>
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||
</span>(5):847–59.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/14985704" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 14985704</span></a>]</div></dd><dt>4.</dt><dd><div class="bk_ref" id="FPWAY18F.REF.4">Karramkam M. , Hinnen F. , Berrehouma M. , Hlavacek C. , Vaufrey F. , Halldin C. , McCarron J.A. , Pike V.W. , Dolle F. Synthesis of a [6-pyridinyl-18F]-labelled fluoro derivative of WAY-100635 as a candidate radioligand for brain 5-HT1A receptor imaging with PET. <span><span class="ref-journal">Bioorg Med Chem. </span>2003;<span class="ref-vol">
|
||
<strong>11</strong>
|
||
</span>(13):2769–82.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12788351" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12788351</span></a>]</div></dd><dt>5.</dt><dd><div class="bk_ref" id="FPWAY18F.REF.5">Lang L. , Jagoda E. , Schmall B. , Sassaman M. , Ma Y. , Eckelman W.C. Fluoro analogs of WAY-100635 with varying pharmacokinetics properties. <span><span class="ref-journal">Nucl Med Biol. </span>2000;<span class="ref-vol">
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||
<strong>27</strong>
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||
</span>(5):457–62.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/10962250" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 10962250</span></a>]</div></dd><dt>6.</dt><dd><div class="bk_ref" id="FPWAY18F.REF.6">Giovacchini G. , Lang L. , Ma Y. , Herscovitch P. , Eckelman W.C. , Carson R.E. Differential effects of paroxetine on raphe and cortical 5-HT1A binding: a PET study in monkeys. <span><span class="ref-journal">Neuroimage. </span>2005;<span class="ref-vol">
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||
<strong>28</strong>
|
||
</span>(1):238–48.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/15993625" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15993625</span></a>]</div></dd><dt>7.</dt><dd><div class="bk_ref" id="FPWAY18F.REF.7">Marchais S. , Nowicki B. , Wikstrom H. , Brennum L.T. , Halldin C. , Pike V.W. Short and efficient syntheses of analogues of WAY-100635: new and potent 5-HT1A receptor antagonists. <span><span class="ref-journal">Bioorg Med Chem. </span>2001;<span class="ref-vol">
|
||
<strong>9</strong>
|
||
</span>(3):695–702.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/11310604" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 11310604</span></a>]</div></dd><dt>8.</dt><dd><div class="bk_ref" id="FPWAY18F.REF.8">Lang L. , Jagoda E. , Schmall B. , Vuong B.K. , Adams H.R. , Nelson D.L. , Carson R.E. , Eckelman W.C. Development of fluorine-18-labeled 5-HT1A antagonists. <span><span class="ref-journal">J Med Chem. </span>1999;<span class="ref-vol">
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||
<strong>42</strong>
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</span>(9):1576–86.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/10229627" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 10229627</span></a>]</div></dd><dt>9.</dt><dd><div class="bk_ref" id="FPWAY18F.REF.9">Ma Y. , Lang L. , Kiesewetter D.O. , Eckelman W.C. Liquid chromatography-tandem mass spectrometry identification of metabolites of three phenylcarboxyl derivatives of the 5-HT(1A) antagonist, N-(2-(4-(2-methoxyphenyl)-1-piperazinyl)ethyl)-N-(2-pyridyl) trans-4-fluorocyclohexanecarboxamide (FCWAY), produced by human and rat hepatocytes. <span><span class="ref-journal">J Chromatogr B Analyt Technol Biomed Life Sci. </span>2002;<span class="ref-vol">
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<strong>780</strong>
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</span>(1):99–110.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12383485" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12383485</span></a>]</div></dd><dt>10.</dt><dd><div class="bk_ref" id="FPWAY18F.REF.10">Jagoda E.M. , Lang L. , Tokugawa J. , Simmons A. , Ma Y. , Contoreggi C. , Kiesewetter D. , Eckelman W.C. Development of 5-HT(1A) receptor radioligands to determine receptor density and changes in endogenous 5-HT. <span><span class="ref-journal">Synapse. </span>2006;<span class="ref-vol">
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<strong>59</strong>
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</span>(6):330–341.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/16440292" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16440292</span></a>]</div></dd><dt>11.</dt><dd><div class="bk_ref" id="FPWAY18F.REF.11">Carson R.E. , Wu Y. , Lang L. , Ma Y. , Der M.G. , Herscovitch P. , Eckelman W.C. Brain uptake of the acid metabolites of F-18-labeled WAY 100635 analogs. <span><span class="ref-journal">J Cereb Blood Flow Metab. </span>2003;<span class="ref-vol">
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<strong>23</strong>
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</span>(2):249–60.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12571456" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12571456</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: NBK23137</span><span class="label">PMID: <a href="https://pubmed.ncbi.nlm.nih.gov/20641340" title="PubMed record of this page" ref="pagearea=meta&targetsite=entrez&targetcat=link&targettype=pubmed">20641340</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/FES-M-4F-18F/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/p-MPPF18F/" title="Next page in this title">Next ></a></div></div></div></div>
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<div xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance"></div><div class="portlet"><div class="portlet_head"><div class="portlet_title"><h3><span>Views</span></h3></div><a name="Shutter" sid="1" href="#" class="portlet_shutter" title="Show/hide content" remembercollapsed="true" pgsec_name="PDF_download" id="Shutter"></a></div><div class="portlet_content"><ul xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="simple-list"><li><a href="/books/NBK23137/?report=reader">PubReader</a></li><li><a href="/books/NBK23137/?report=printable">Print View</a></li><li><a data-jig="ncbidialog" href="#_ncbi_dlg_citbx_NBK23137" data-jigconfig="width:400,modal:true">Cite this Page</a><div id="_ncbi_dlg_citbx_NBK23137" style="display:none" title="Cite this Page"><div class="bk_tt">Cheng KT. 4-(2´-Methoxyphenyl)-1-[2´-(N-2´´-1,3 pyrimidino)-p-[18F]fluorobenzamido]ethylpiperazine. 2005 Feb 1 [Updated 2008 Jun 30]. In: Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. <span class="bk_cite_avail"></span></div></div></li><li><a href="/books/NBK23137/pdf/Bookshelf_NBK23137.pdf">PDF version of this page</a> (146K)</li><li><a href="/books/n/micad/toc/bin/micad.csv">MICAD summary (CSV file)</a></li></ul></div></div><div class="portlet"><div class="portlet_head"><div class="portlet_title"><h3><span>In this page</span></h3></div><a name="Shutter" sid="1" href="#" class="portlet_shutter" title="Show/hide content" remembercollapsed="true" pgsec_name="page-toc" id="Shutter"></a></div><div class="portlet_content"><ul xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="simple-list"><li><a href="#FPWAY18F.Background" ref="log$=inpage&link_id=inpage">Background</a></li><li><a href="#FPWAY18F.Synthesis" ref="log$=inpage&link_id=inpage">Synthesis</a></li><li><a href="#FPWAY18F.In_Vitro_Studies_Tes" ref="log$=inpage&link_id=inpage"><i>In Vitro</i> Studies: Testing in Cells and Tissues</a></li><li><a href="#FPWAY18F.Animal_Studies" ref="log$=inpage&link_id=inpage">Animal Studies</a></li><li><a href="#FPWAY18F.Human_Studies" ref="log$=inpage&link_id=inpage">Human Studies</a></li><li><a href="#FPWAY18F.NIH_Support" ref="log$=inpage&link_id=inpage">NIH Support</a></li><li><a href="#FPWAY18F.references" ref="log$=inpage&link_id=inpage">References</a></li></ul></div></div><div class="portlet"><div class="portlet_head"><div class="portlet_title"><h3><span>Search MICAD</span></h3></div><a name="Shutter" sid="1" href="#" class="portlet_shutter" title="Show/hide content" remembercollapsed="true" pgsec_name="source-application" id="Shutter"></a></div><div class="portlet_content"><form xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" name="frmSearch" method="get" action="/books/NBK5330/" id="frmSearch"><script type="text/javascript" src="/corehtml/pmc//js/bookshelf/micad.js">/**/</script><label class="offscreen_noflow" for="txtfield">Search term</label><input id="txtfield" type="text" name="f1_term" size="22" onKeyPress="KeyPress('micad',event,'/books/NBK5330/','')" /><button name="f1_search" type="submit">Go</button><button onclick="this.form.reset();" type="reset">Clear</button><p><b>Limit my Search:</b></p><div class="clearfix"><label for="detection">Method of detection:</label><div class="right"><select name="detection" id="detection" style="width:200px"><option value="" selected="selected">Any</option><option value="(MRI OR "Magnetic resonance imaging" OR MRS)">MRI</option><option value="Multimodal">Multimodal imaging</option><option value="Optical">Optical imaging</option><option value="PET">PET</option><option value="Photoacoustic">Photoacoustic imaging</option><option value="(SPECT OR planar)">SPECT</option><option value="Ultrasound">Ultrasound</option><option value="(x-ray OR ct)">X-ray, CT</option></select></div></div><div class="clearfix"><label for="signal">Source of signal/contrast:</label><div class="right"><select name="signal" id="signal" style="width:200px"><option value="" selected="selected">Any</option><optgroup label="MRI agents"><option value="(Copper OR Cu)">Copper</option><option value="(Europium OR Eu3+)">Europium</option><option value="(Fluorine OR 19F)">Fluorine</option><option value="(Gadolinium OR Gd3+)">Gadolinium</option><option value=""Hyperpolarized 13C"">Hyperpolarized 13C</option><option value=""Iron oxide"">Iron oxide</option><option value=""Nitroxide radicals"">Nitroxide radicals</option><option value="(Oxygen OR 17O)">Oxygen</option><option value="Thulium">Thulium</option></optgroup><optgroup label="Multimodal agents"><option value="((Gadolinium OR Gd3+) AND Optical)">Gadolinium and optical</option><option value="((Gadolinium OR Gd3+) AND (Gold OR Au))">Gadolinium and Gold</option><option value="("Iron oxide" AND (64Cu OR 124I OR 111In))">Iron oxide and
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/><label for="__micad_btn_6">Any</label></div></form><form xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" name="frmGo" method="get" action="javascript:alert('frmGo:_@action_was_not_set')" id="frmGo"><input name="term" value="." type="hidden" /></form></div></div><div class="portlet"><div class="portlet_head"><div class="portlet_title"><h3><span>Related information</span></h3></div><a name="Shutter" sid="1" href="#" class="portlet_shutter" title="Show/hide content" remembercollapsed="true" pgsec_name="discovery_db_links" id="Shutter"></a></div><div class="portlet_content"><ul><li class="brieflinkpopper"><a class="brieflinkpopperctrl" href="/books/?Db=pubmed&DbFrom=books&Cmd=Link&LinkName=books_pubmed_refs&IdsFromResult=1503416" ref="log$=recordlinks">PubMed</a><div class="brieflinkpop offscreen_noflow">Links to PubMed</div></li></ul></div></div><div class="portlet"><div class="portlet_head"><div 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