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<title>99mTc-Labeled 1-hydroxy-2-(2-isopropyl-1H-imidazole-1-yl)ethylidene-1,1-bisphosphonic acid - 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="99mTc-Labeled 1-hydroxy-2-(2-isopropyl-1H-imidazole-1-yl)ethylidene-1,1-bisphosphonic acid" /><meta name="citation_publisher" content="National Center for Biotechnology Information (US)" /><meta name="citation_date" content="2011/11/01" /><meta name="citation_author" content="Arvind Chopra" /><meta name="citation_pmid" content="22171391" /><meta name="citation_fulltext_html_url" content="https://www.ncbi.nlm.nih.gov/books/NBK82382/" /><link rel="schema.DC" href="http://purl.org/DC/elements/1.0/" /><meta name="DC.Title" content="99mTc-Labeled 1-hydroxy-2-(2-isopropyl-1H-imidazole-1-yl)ethylidene-1,1-bisphosphonic acid" /><meta name="DC.Type" content="Text" /><meta name="DC.Publisher" content="National Center for Biotechnology Information (US)" /><meta name="DC.Contributor" content="Arvind Chopra" /><meta name="DC.Date" content="2011/11/01" /><meta name="DC.Identifier" content="https://www.ncbi.nlm.nih.gov/books/NBK82382/" /><meta name="description" content="Bisphosphonates (BPs; also known as diphosphonates) labeled with technetium ([99mTc]-BPs) are often used in bone scintigraphy to detect osteoporosis and other skeletal-related events (SREs), including bone metastases (1). 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Bone scintigraphy is usually performed 2–6 h after intravenous injection of a [99mTc]-BP, resulting in exposure of the patient to radiation for an extended time (due to slow clearance from circulation). To develop BPs that are more efficient and require only a short waiting time before bone scintigraphy, investigators generated various BPs, such as zoledronic acid (ZL), which contains an imidazole group in its structure, and evaluated their efficacy for the treatment of various bone-related diseases (5, 6). 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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="#__NBK82382_dtls__">Show details</a><div style="display:none" class="ui-widget" id="__NBK82382_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/EMIDP99mTc/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/IPrDP99mTc/" 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="_NBK82382_"><span class="title" itemprop="name"><sup>99m</sup>Tc-Labeled 1-hydroxy-2-(2-isopropyl-1H-imidazole-1-yl)ethylidene-1,1-bisphosphonic acid</span></h1><div itemprop="alternativeHeadline" class="subtitle whole_rhythm"> [<sup>99m</sup>Tc]-iPIDP</div><p class="contrib-group"><span itemprop="author">Arvind Chopra</span>, PhD.</p><a data-jig="ncbitoggler" href="#__NBK82382_ai__" style="border:0;text-decoration:none">Author Information and Affiliations</a><div style="display:none" class="ui-widget" id="__NBK82382_ai__"><div class="contrib half_rhythm"><span itemprop="author">Arvind Chopra</span>, PhD<div class="affiliation small">National Center for Biotechnology Information, NLM, Bethesda, MD 20894<div><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></div></div></div></div><p class="small">Created: <span itemprop="datePublished">October 24, 2011</span>; Last Update: <span itemprop="dateModified">November 1, 2011</span>.</p></div><div class="jig-ncbiinpagenav body-content whole_rhythm" data-jigconfig="allHeadingLevels: ['h2'],smoothScroll: false" itemprop="text"><div id="iPIDP99mTc.T.nc_chemical_name99mtclabele" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK82382/table/iPIDP99mTc.T.nc_chemical_name99mtclabele/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__iPIDP99mTc.T.nc_chemical_name99mtclabele_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;"><sup>99m</sup>Tc-Labeled 1-hydroxy-2-(2-isopropyl-1H-imidazole-1-yl)ethylidene-1,1-bisphosphonic acid</td><td rowspan="9" colspan="1" style="text-align:center;vertical-align:middle;">
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<a href="https://pubchem.ncbi.nlm.nih.gov/substance/126920289" 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=126920289" alt="image 126920289 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>99m</sup>Tc]-iPIDP</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;"></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;">Bone (hydroxyapatite) at low concentration; farnesyl disphosphate (pyrophosphate) synthase (molecular target) at high concentration</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;">Other (Tissue); enzyme</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;">Single-photon emission computed tomography (SPECT); gamma planar imaging</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>99m</sup>Tc</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><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><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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</td><td rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Click on above structure of iPIDP for 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="iPIDP99mTc.Background"><h2 id="_iPIDP99mTc_Background_">Background</h2><p>[<a href="/pubmed?term=Bisphosphonates&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Bisphosphonates (BPs; also known as diphosphonates) labeled with technetium ([<sup>99m</sup>Tc]-BPs) are often used in bone scintigraphy to detect osteoporosis and other skeletal-related events (SREs), including bone metastases (<a class="bk_pop" href="#iPIDP99mTc.REF.1">1</a>). These chemicals are known to promote osteoclast apoptosis and have a strong affinity for hydroxyapatite, a component of the bone matrix. The mechanism of action of these bone-seeking compounds is described in detail elsewhere (<a class="bk_pop" href="#iPIDP99mTc.REF.2" data-bk-pop-others="iPIDP99mTc.REF.3 iPIDP99mTc.REF.4">2-4</a>). Bone scintigraphy is usually performed 2–6 h after intravenous injection of a [<sup>99m</sup>Tc]-BP, resulting in exposure of the patient to radiation for an extended time (due to slow clearance from circulation). To develop BPs that are more efficient and require only a short waiting time before bone scintigraphy, investigators generated various BPs, such as <a href="http://www.pharma.us.novartis.com/product/pi/pdf/Zometa.pdf" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">zoledronic acid</a> (ZL), which contains an imidazole group in its structure, and evaluated their efficacy for the treatment of various bone-related diseases (<a class="bk_pop" href="#iPIDP99mTc.REF.5" data-bk-pop-others="iPIDP99mTc.REF.6">5, 6</a>). ZL was determined to be the most potent BP available for treating bone resorption and is approved by the United States Food and Drug Administration for the treatment of various tumor-induced SREs (<a class="bk_pop" href="#iPIDP99mTc.REF.7">7</a>).</p><p>In an earlier study to further improve the potency of ZL, the imidazole group of the compound was modified to obtain 1-hydroxy-2-(2-ethyl-4-methyl-1H-imidazole-1-yl)ethane-1,1-diyldiphosphonic acid (EMIDP), and the chemical was labeled with <sup>99m</sup>Tc to produce [<sup>99m</sup>Tc]-EMIDP (<a class="bk_pop" href="#iPIDP99mTc.REF.1">1</a>). The biodistribution of [<sup>99m</sup>Tc]-EMIDP was investigated in normal mice, and the radiochemical was evaluated as a bone-imaging agent in rabbits. From these studies, the investigators concluded that [<sup>99m</sup>Tc]-EMIDP bound selectively to the skeletal tissue in rabbits with superior selectivity compared to that of <sup>99m</sup>Tc-labeled methylene diphosphonate ([<sup>99m</sup>Tc]-MDP), another BP that is commonly used in the clinic. In a effort to further explore the possibility of generating a high-potency ZL derivative similar to EMIDP, Lin et al. investigated optimization of the linker chain between the imidazolyl and the germinal BP group in the structure of ZL (<a class="bk_pop" href="#iPIDP99mTc.REF.8">8</a>). For this, a ZL derivative, 1-hydroxy-3-(1H-imidazol-1-yl)propane-1,1-diyldiphosphonic acid was synthesized and labeled with <sup>99m</sup>Tc, and its biodistribution and bone-imaging properties (with single-photon emission computed tomography (SPECT) imaging) were investigated in normal mice and rabbits, respectively (<a class="bk_pop" href="#iPIDP99mTc.REF.8">8</a>). As a continuation of this work, another ZL derivative with 2-isopropyl on the imidazole ring, 1-hydroxy-2-(2-isopropyl-1H-imidazole-1-yl)ethylidene-1,1-bisphosphonic acid (iPIDP), was prepared and labeled with <sup>99m</sup>Tc (to produce [<sup>99m</sup>Tc]-iPIDP), and the biodistribution of the labeled compound was investigated in mice (<a class="bk_pop" href="#iPIDP99mTc.REF.9">9</a>). In addition, the investigators used SPECT to study the bone-imaging characteristics of [<sup>99m</sup>Tc]-iPIDP in rabbits.</p><div id="iPIDP99mTc.Related_Resource_Links"><h3>Related Resource Links</h3><p><a href="/books/?term=MDP+AND+micad%5Bbook%5D&view=chapter&p%24a=&p%24l=PBooksLayout&p%24st=books" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Related chapters</a> in MICAD</p><p><a href="/nuccore/NM_001037277.1" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Protein and mRNA sequence</a> of human farnesyl diphosphate synthase</p><p><a href="/gene/2224" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Gene information</a> regarding human farnesyl diphosphate synthase (GeneID: 2224)</p><p>Farnesyl diphosphate synthase in <a href="/omim/134629" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Online Mendelian Inheritance in Man (OMIM)</a></p><p><a href="/Structure/mmdb/mmdbsrv.cgi?uid=59201" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Structure of farnesyl diphosphate synthase</a> complexed with a bisphosphonate</p><p>Farnesyl diphosphate synthase in <a href="http://www.genome.jp/dbget-bin/www_bget?pathway+hsa00900" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Kyoto Encyclopedia of Genes and Genomes (KEGG) Pathways</a></p><p><a href="http://clinicaltrials.gov/ct2/results?term=bisphosphonates" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">Clinical trials</a> with bisphosphonates (or diphosphonates)</p></div></div><div id="iPIDP99mTc.Synthesis"><h2 id="_iPIDP99mTc_Synthesis_">Synthesis</h2><p>[<a href="/pubmed?term=1-hydroxy-2-%282-isopropyl-1H-imidazole-1-yl%29%20ethylidene-1%2C1-bisphosphonic%20synthesis&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>The synthesis and <sup>99m</sup>Tc labeling of iPIDP has been described by Wang et al. (<a class="bk_pop" href="#iPIDP99mTc.REF.9">9</a>). The radiochemical purity (RCP) of [<sup>99m</sup>Tc]-iPIDP was reported to be >95%. The radiochemical yield (RCY) and specific activity of the labeled compound was not reported.</p><p>In one of the studies, <sup>99m</sup>Tc-labeled ZL ([<sup>99m</sup>Tc]-ZL) was also used for comparison purposes, but the RCY, RCP, and specific activity of this labeled compound were not reported (<a class="bk_pop" href="#iPIDP99mTc.REF.9">9</a>).</p></div><div id="iPIDP99mTc.In_Vitro_Studies_Testing_in_C"><h2 id="_iPIDP99mTc_In_Vitro_Studies_Testing_in_C_"><i>In Vitro</i> Studies: Testing in Cells and Tissues</h2><p>[<a href="/pubmed?term=iPIDP%20in%20vitro%20studies%5ball%5d&cmd=correctspelling" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>The <i>in vitro</i> stability of [<sup>99m</sup>Tc]-iPIDP was investigated by incubating the radiolabeled compound for 6 h at room temperature in phosphate buffered saline (pH 4.0-6.0), and the RCP of the tracer was evaluated every 0.5 h with paper chromatography (<a class="bk_pop" href="#iPIDP99mTc.REF.9">9</a>). At the end of the 6-h incubation, the RCP of [<sup>99m</sup>Tc]-iPIDP was reported to be 96.6 ± 0.3%. This indicated that the tracer was stable at room temperature for at least 6 h.</p></div><div id="iPIDP99mTc.Animal_Studies"><h2 id="_iPIDP99mTc_Animal_Studies_">Animal Studies</h2><div id="iPIDP99mTc.Rodents"><h3>Rodents</h3><p>[<a href="/pubmed?term=99mTc-iPIDP%20rodentia&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>Wang et al. investigated the biodistribution of [<sup>99m</sup>Tc]-iPIDP in Institute of Cancer Research mice (<a class="bk_pop" href="#iPIDP99mTc.REF.9">9</a>). The animals (<i>n</i> = 5 mice/group) were injected with freshly prepared [<sup>99m</sup>Tc]-iPIDP through the lateral tail vein, and the mice were euthanized at predetermined time points from 5 min to 240 min (4 h) postinjection (p.i.) to determine the amount of radioactivity accumulated in the major organs, including bone. Data from the study were presented as percent uptake of injected dose per gram tissue (% ID/g). The bone showed an accumulation of 3.96 ± 0.37% ID/g at 5 min p.i., which increased to 9.63 ± 0.64% ID/g at 60 min p.i. and decreased to 4.57 ± 0.14% ID/g at 240 min p.i. Among the other organs, the kidneys showed the highest uptake with 10.01 ± 0.68% ID/g at 5 min p.i., which decreased to 1.39 ± 0.01% ID/g at 240 min p.i. A similar trend in the uptake of radioactivity was observed in the other non-target organs. The bone/organ uptake ratios for muscle, spleen, brain, lung, heart, and liver were 12.19, 15.32, 95.55, 3.32, 8.78, and 11.22, respectively, at 15 min p.i. and increased to 67.83, 73.91, 429.06, 24.02, 66.00, and 37.45, respectively, at 60 min p.i. This indicated that accumulation of radioactivity in the soft tissue was low compared to the bone and that it was cleared rapidly from the soft tissues. No blocking studies were reported.</p></div><div id="iPIDP99mTc.Other_NonPrimate_Mammals"><h3>Other Non-Primate Mammals</h3><p>[<a href="/pubmed?term=99mTc-iPIDP%20rabbit&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>For bone imaging, a New Zealand white rabbit (under anesthesia) was injected with [<sup>99m</sup>Tc]-iPIDP through the marginal ear vein, and dynamic images of the animal were acquired every 5 min for the next 60 min. This was followed by the acquisition of static images every hour for 4 h (<a class="bk_pop" href="#iPIDP99mTc.REF.9">9</a>). From the images it was clear that radioactivity in the animals was present selectively in the bones, and a low amount of the tracer was present in the various soft tissues, except in the kidneys and the bladder. These results were consistent with observations made during the biodistribution studies and showed that the radioactivity was cleared from circulation primarily through the urinary route.</p><p>For comparison with [<sup>99m</sup>Tc]-iPIPD, dynamic bone images were also acquired from a New Zealand white rabbit injected with [<sup>99m</sup>Tc]-ZL as described above (<a class="bk_pop" href="#iPIDP99mTc.REF.9">9</a>). Images obtained with [<sup>99m</sup>Tc]-ZL showed that both tracers had similar biodistribution patterns in the bones and the soft tissues. However, compared to [<sup>99m</sup>Tc]-iPIPD, with [<sup>99m</sup>Tc]-ZL there was a significantly higher (<i>P</i> value not reported) accumulation of radioactivity in the liver at the various time points.</p><p>Static images acquired from the animals with the two tracers showed that the rabbit skeleton was clearly visible with both [<sup>99m</sup>Tc]-iPIPD and [<sup>99m</sup>Tc]-ZL at 1 h p.i (<a class="bk_pop" href="#iPIDP99mTc.REF.9">9</a>). A comparison of the images obtained with the two radiochemicals showed that with [<sup>99m</sup>Tc]-iPIPDuptake of radioactivity by the liver was significantly lower than that with [<sup>99m</sup>Tc]-ZL. Even at 4 h p.i., the liver was clearly visible with [<sup>99m</sup>Tc]-ZL, indicating that the clearance of this tracer from the organ was more gradual than that of [<sup>99m</sup>Tc]-iPIPD.</p><p>From these studies, the investigators concluded that [<sup>99m</sup>Tc]-iPIPD was a promising agent for bone imaging in animals; however, further studies are necessary before it can be used in the clinic (<a class="bk_pop" href="#iPIDP99mTc.REF.9">9</a>).</p></div><div id="iPIDP99mTc.NonHuman_Primates"><h3>Non-Human Primates</h3><p>[<a href="/pubmed?term=99mTc-iPIDP%20Non-Human%20Primates&cmd=DetailsSearch" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div></div><div id="iPIDP99mTc.Human_Studies"><h2 id="_iPIDP99mTc_Human_Studies_">Human Studies</h2><p>[<a href="/pubmed?term=99mTc-iPIDP%20Human%20Studies" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">PubMed</a>]</p><p>No publication is currently available.</p></div><div id="iPIDP99mTc.Supplemental_Information"><h2 id="_iPIDP99mTc_Supplemental_Information_">Supplemental Information</h2><p>[<a href="/books/n/micad/disclaimer/">Disclaimers</a>]</p><p>No information is currently available.</p></div><div id="iPIDP99mTc.References"><h2 id="_iPIDP99mTc_References_">References</h2><dl class="temp-labeled-list"><dt>1.</dt><dd><div class="bk_ref" id="iPIDP99mTc.REF.1">Lin J., Luo S., Chen C., Qiu L., Wang Y., Cheng W., Ye W., Xia Y.
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<em>Preparation and preclinical pharmacological study on a novel bone imaging agent (99m)Tc-EMIDP.</em>
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<span><span class="ref-journal">Appl Radiat Isot. </span>2010;<span class="ref-vol">68</span>(9):1616–22.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/20363146" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 20363146</span></a>]</div></dd><dt>2.</dt><dd><div class="bk_ref" id="iPIDP99mTc.REF.2">Kimmel D.B.
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<em>Mechanism of action, pharmacokinetic and pharmacodynamic profile, and clinical applications of nitrogen-containing bisphosphonates.</em>
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||
<span><span class="ref-journal">J Dent Res. </span>2007;<span class="ref-vol">86</span>(11):1022–33.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/17959891" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 17959891</span></a>]</div></dd><dt>3.</dt><dd><div class="bk_ref" id="iPIDP99mTc.REF.3">Zhang Y., Cao R., Yin F., Hudock M.P., Guo R.T., Krysiak K., Mukherjee S., Gao Y.G., Robinson H., Song Y., No J.H., Bergan K., Leon A., Cass L., Goddard A., Chang T.K., Lin F.Y., Van Beek E., Papapoulos S., Wang A.H., Kubo T., Ochi M., Mukkamala D., Oldfield E.
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||
<em>Lipophilic bisphosphonates as dual farnesyl/geranylgeranyl diphosphate synthase inhibitors: an X-ray and NMR investigation.</em>
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||
<span><span class="ref-journal">J Am Chem Soc. </span>2009;<span class="ref-vol">131</span>(14):5153–62.</span> [<a href="/pmc/articles/PMC2753403/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC2753403</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/19309137" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 19309137</span></a>]</div></dd><dt>4.</dt><dd><div class="bk_ref" id="iPIDP99mTc.REF.4">Mitterhauser M., Toegel S.
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<em>Radiopharmaceutical considerations on bone seeker uptake: should we learn from therapeutical targets of bisphosphonates?</em>
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<span><span class="ref-journal">Nucl Med Biol. </span>2011;<span class="ref-vol">38</span>(5):617–8.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/21718935" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 21718935</span></a>]</div></dd><dt>5.</dt><dd><div class="bk_ref" id="iPIDP99mTc.REF.5">Widler L., Jaeggi K.A., Glatt M., Muller K., Bachmann R., Bisping M., Born A.R., Cortesi R., Guiglia G., Jeker H., Klein R., Ramseier U., Schmid J., Schreiber G., Seltenmeyer Y., Green J.R.
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<em>Highly potent geminal bisphosphonates. From pamidronate disodium (Aredia) to zoledronic acid (Zometa).</em>
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<span><span class="ref-journal">J Med Chem. </span>2002;<span class="ref-vol">45</span>(17):3721–38.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12166945" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12166945</span></a>]</div></dd><dt>6.</dt><dd><div class="bk_ref" id="iPIDP99mTc.REF.6">Asikoglu M., Durak F.G.
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<em>The rabbit biodistribution of a therapeutic dose of zoledronic acid labeled with Tc-99m.</em>
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<span><span class="ref-journal">Appl Radiat Isot. </span>2009;<span class="ref-vol">67</span>(9):1616–21.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/19457677" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 19457677</span></a>]</div></dd><dt>7.</dt><dd><div class="bk_ref" id="iPIDP99mTc.REF.7">Smith M.R.
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<em>Osteoclast targeted therapy for prostate cancer: bisphosphonates and beyond.</em>
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||
<span><span class="ref-journal">Urol Oncol. </span>2008;<span class="ref-vol">26</span>(4):420–5.</span> [<a href="/pmc/articles/PMC3090666/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC3090666</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/18593621" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 18593621</span></a>]</div></dd><dt>8.</dt><dd><div class="bk_ref" id="iPIDP99mTc.REF.8">Lin J., Qiu L., Cheng W., Luo S., Ye W.
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<em>Preparation and in vivo biological investigations on a novel radioligand for bone scanning: technetium-99m-labeled zoledronic acid derivative.</em>
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<span><span class="ref-journal">Nucl Med Biol. </span>2011;<span class="ref-vol">38</span>(5):619–29.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/21718936" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 21718936</span></a>]</div></dd><dt>9.</dt><dd><div class="bk_ref" id="iPIDP99mTc.REF.9">Wang Y., Luo S., Lin J., Qiu L., Cheng W., Zhai H., Nan B., Ye W., Xia Y.
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<em>Animal studies of 99mTc-i-PIDP: a new bone imaging agent.</em>
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<span><span class="ref-journal">Appl Radiat Isot. </span>2011;<span class="ref-vol">69</span>(9):1169–75.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/21507669" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 21507669</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: NBK82382</span><span class="label">PMID: <a href="https://pubmed.ncbi.nlm.nih.gov/22171391" title="PubMed record of this page" ref="pagearea=meta&targetsite=entrez&targetcat=link&targettype=pubmed">22171391</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/EMIDP99mTc/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/micad/IPrDP99mTc/" 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/NBK82382/?report=reader">PubReader</a></li><li><a href="/books/NBK82382/?report=printable">Print View</a></li><li><a data-jig="ncbidialog" href="#_ncbi_dlg_citbx_NBK82382" data-jigconfig="width:400,modal:true">Cite this Page</a><div id="_ncbi_dlg_citbx_NBK82382" style="display:none" title="Cite this Page"><div class="bk_tt">Chopra A. 99mTc-Labeled 1-hydroxy-2-(2-isopropyl-1H-imidazole-1-yl)ethylidene-1,1-bisphosphonic acid. 2011 Oct 24 [Updated 2011 Nov 1]. 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/NBK82382/pdf/Bookshelf_NBK82382.pdf">PDF version of this page</a> (141K)</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="#iPIDP99mTc.Background" ref="log$=inpage&link_id=inpage">Background</a></li><li><a href="#iPIDP99mTc.Synthesis" ref="log$=inpage&link_id=inpage">Synthesis</a></li><li><a href="#iPIDP99mTc.In_Vitro_Studies_Testing_in_C" ref="log$=inpage&link_id=inpage"><i>In Vitro</i> Studies: Testing in Cells and Tissues</a></li><li><a href="#iPIDP99mTc.Animal_Studies" ref="log$=inpage&link_id=inpage">Animal Studies</a></li><li><a href="#iPIDP99mTc.Human_Studies" ref="log$=inpage&link_id=inpage">Human Studies</a></li><li><a href="#iPIDP99mTc.Supplemental_Information" ref="log$=inpage&link_id=inpage">Supplemental Information</a></li><li><a href="#iPIDP99mTc.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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xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="invert">Review</span> (99m)Tc-Labeled 1-hydroxy-3-(1H-imidazol-1-yl)propane-1,1-diyldiphosphonic acid (IPrDP).</a><span class="source">[Molecular Imaging and Contrast...]</span><div class="brieflinkpop offscreen_noflow"><span xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="invert">Review</span> (99m)Tc-Labeled 1-hydroxy-3-(1H-imidazol-1-yl)propane-1,1-diyldiphosphonic acid (IPrDP).<div class="brieflinkpopdesc"><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="author">Chopra A. </em><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="cit">Molecular Imaging and Contrast Agent Database (MICAD). 2004</em></div></div></li><li class="brieflinkpopper two_line"><a class="brieflinkpopperctrl" 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