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<meta name="robots" content="INDEX,FOLLOW,NOARCHIVE" /><meta name="citation_inbook_title" content="LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]" /><meta name="citation_title" content="Tadalafil" /><meta name="citation_publisher" content="National Institute of Diabetes and Digestive and Kidney Diseases" /><meta name="citation_date" content="2017/08/02" /><meta name="citation_pmid" content="31643246" /><meta name="citation_fulltext_html_url" content="https://www.ncbi.nlm.nih.gov/books/NBK547910/" /><link rel="schema.DC" href="http://purl.org/DC/elements/1.0/" /><meta name="DC.Title" content="Tadalafil" /><meta name="DC.Type" content="Text" /><meta name="DC.Publisher" content="National Institute of Diabetes and Digestive and Kidney Diseases" /><meta name="DC.Date" content="2017/08/02" /><meta name="DC.Identifier" content="https://www.ncbi.nlm.nih.gov/books/NBK547910/" /><meta name="description" content="Tadalafil (ta da' la fil) is a selective inhibitor of phosphodiesterase type 5 (PDE5), which mediates the breakdown of cyclic guanosine monophosphate (cGMP) inducing smooth muscle relaxation in the corpus cavernosum of the penis and in the pulmonary vasculature where this specific phosphodiesterase is found. Tadalafil is effective in prolonging erection and was approved for treatment of erectile dysfunction in the United States in 2003 and for the treatment of pulmonary hypertension and symptoms of benign prostatic hypertrophy in 2011. Tadalafil is available in tablets of 2.5, 5, 10 and 20 mg under the brand name of Cialis for erectile dysfunction and benign prostatic hyperplasia, and in 20 mg tablets under the brand name Adcirca for pulmonary hypertension. The recommended dose for erectile dysfunction is 10 mg as a single dose as needed approximately one hour before sexual activity. The dose can be increased or decreased based upon effect and tolerance, with a recommended maximum frequency of once daily and maximum dosage of 20 mg. The approved dose for pulmonary hypertension is 40 mg once daily. Common side effects include dizziness, headache, flushing, hypotension, rhinitis and dyspepsia. 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Tadalafil is available in tablets of 2.5, 5, 10 and 20 mg under the brand name of Cialis for erectile dysfunction and benign prostatic hyperplasia, and in 20 mg tablets under the brand name Adcirca for pulmonary hypertension. The recommended dose for erectile dysfunction is 10 mg as a single dose as needed approximately one hour before sexual activity. The dose can be increased or decreased based upon effect and tolerance, with a recommended maximum frequency of once daily and maximum dosage of 20 mg. The approved dose for pulmonary hypertension is 40 mg once daily. Common side effects include dizziness, headache, flushing, hypotension, rhinitis and dyspepsia. 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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>LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012-. </p></div><div class="iconblock clearfix whole_rhythm no_top_margin bk_noprnt"><a class="img_link icnblk_img" title="All Drug Records" href="/books/n/livertox/"><img class="source-thumb" src="/corehtml/pmc/pmcgifs/bookshelf/thumbs/th-livertox-lrg.png" alt="Cover of LiverTox" height="100px" width="80px" /></a><div class="icnblk_cntnt eight_col"><h2>LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet].</h2><a data-jig="ncbitoggler" href="#__NBK547910_dtls__">Show details</a><div style="display:none" class="ui-widget" id="__NBK547910_dtls__"><div>Bethesda (MD): <a href="https://www.niddk.nih.gov/" ref="pagearea=page-banner&targetsite=external&targetcat=link&targettype=publisher">National Institute of Diabetes and Digestive and Kidney Diseases</a>; 2012-.</div></div><div class="half_rhythm"><ul class="inline_list"><li style="margin-right:1em"><a class="bk_cntns" href="/books/n/livertox/">Drug Records</a></li></ul></div><div class="bk_noprnt"><form method="get" action="/books/n/livertox/" 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/livertox/Tacrolimus/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/livertox/Tafamidis/" 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="_NBK547910_"><span class="title" itemprop="name">Tadalafil</span></h1><p class="small">Last Update: <span itemprop="dateModified">August 2, 2017</span>.</p></div><div class="body-content whole_rhythm" itemprop="text"><div id="Tadalafil.OVERVIEW"><h2 id="_Tadalafil_OVERVIEW_">OVERVIEW</h2><div id="Tadalafil.Introcuction"><h3>Introcuction</h3><p>Tadalafil is a selective inhibitor of phosphodiesterase type 5 (PDE5) and is used as therapy of erectile dysfunction and pulmonary hypertension. Tadalafil therapy has not been associated with serum aminotransferase elevations, but has been linked to at least one published case of clinically apparent liver injury.</p></div><div id="Tadalafil.Background"><h3>Background</h3><p>Tadalafil (ta da' la fil) is a selective inhibitor of phosphodiesterase type 5 (PDE5), which mediates the breakdown of cyclic guanosine monophosphate (cGMP) inducing smooth muscle relaxation in the corpus cavernosum of the penis and in the pulmonary vasculature where this specific phosphodiesterase is found. Tadalafil is effective in prolonging erection and was approved for treatment of erectile dysfunction in the United States in 2003 and for the treatment of pulmonary hypertension and symptoms of benign prostatic hypertrophy in 2011. Tadalafil is available in tablets of 2.5, 5, 10 and 20 mg under the brand name of Cialis for erectile dysfunction and benign prostatic hyperplasia, and in 20 mg tablets under the brand name Adcirca for pulmonary hypertension. The recommended dose for erectile dysfunction is 10 mg as a single dose as needed approximately one hour before sexual activity. The dose can be increased or decreased based upon effect and tolerance, with a recommended maximum frequency of once daily and maximum dosage of 20 mg. The approved dose for pulmonary hypertension is 40 mg once daily. Common side effects include dizziness, headache, flushing, hypotension, rhinitis and dyspepsia. Rare, but potentially serious adverse events inlucding vision and hearing loss, hypotension, cardiovascular events and priapism.</p></div><div id="Tadalafil.Hepatotoxicity"><h3>Hepatotoxicity</h3><p>Despite fairly extensive use, tadalafil has been linked to only rare reports of serum aminotransferase elevations and clinically apparent liver injury. In a single case report, tadalafil was linked to cholestatic hepatitis arising within a few days of starting the medication. Immunoallergic features and autoantibodies were not present. The injury was self-limiting without residual evidence of bile duct injury. The related PDE5 inhibitor, sildenafil, has also been associated with rare cases of acute cholestatic liver injury with jaundice.</p><p><a class="def" href="/books/n/livertox/glossary/def-item/glossary.likelihood-score/">Likelihood score</a>: D (possible rare cause of clinically apparent liver injury).</p></div><div id="Tadalafil.Mechanism_of_Injury"><h3>Mechanism of Injury</h3><p>The mechanism of liver injury from tadalafil is unknown, but it is metabolized in the liver via the cytochrome P450 system (CYP 3A4) and a toxic or immunogenic intermediate may account for the rare instances of hepatic injury linked to its use.</p></div><div id="Tadalafil.Outcome_and_Management"><h3>Outcome and Management</h3><p>The liver injury linked to tadalafil has been self-limited and resolving within 2 to 3 months. Tadalafil has not been linked to cases of acute liver failure, chronic hepatitis or vanishing bile duct syndrome. There is no known cross sensitivity between tadalafil and the other PDE5 inhibitors currently in use in the United States, but switching to another PDE5 inhibitor should be done with caution.</p><p>References to the safety and potential hepatotoxicity of tadalafil are provided in the Overview section on PDE5 Inhibitors.</p><p>Drug Class: <a href="/books/n/livertox/PDE5Inhibitors/">PDE5 Inhibitors</a></p><p>Other Drugs in the Class: <a href="/books/n/livertox/Avanafil/">Avanafil</a>, <a href="/books/n/livertox/Sildenafil/">Sildenafil</a>, <a href="/books/n/livertox/Vardenafil/">Vardenafil</a></p></div></div><div id="Tadalafil.PRODUCT_INFORMATION"><h2 id="_Tadalafil_PRODUCT_INFORMATION_">PRODUCT INFORMATION</h2><div id="Tadalafil.BPI" class="box"><p>
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<b>REPRESENTATIVE TRADE NAMES</b>
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</p><p>Tadalafil – Cialis®</p><p>
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<b>DRUG CLASS</b>
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</p><p>PDE5 Inhibitors</p><p>
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<a href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=all&query=tadalafil" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">COMPLETE LABELING</a>
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</p><p>Product labeling at DailyMed, National Library of Medicine, NIH</p></div></div><div id="Tadalafil.CHEMICAL_FORMULA_AND_STRUCTURE"><h2 id="_Tadalafil_CHEMICAL_FORMULA_AND_STRUCTURE_">CHEMICAL FORMULA AND STRUCTURE</h2><div id="Tadalafil.T1" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK547910/table/Tadalafil.T1/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__Tadalafil.T1_lrgtbl__"><table><thead><tr><th id="hd_h_Tadalafil.T1_1_1_1_1" rowspan="1" colspan="1" style="vertical-align:top;">DRUG</th><th id="hd_h_Tadalafil.T1_1_1_1_2" rowspan="1" colspan="1" style="vertical-align:top;">CAS REGISTRY NO</th><th id="hd_h_Tadalafil.T1_1_1_1_3" rowspan="1" colspan="1" style="vertical-align:top;">MOLECULAR FORMULA</th><th id="hd_h_Tadalafil.T1_1_1_1_4" rowspan="1" colspan="1" style="vertical-align:top;">STRUCTURE</th></tr></thead><tbody><tr><td headers="hd_h_Tadalafil.T1_1_1_1_1" rowspan="1" colspan="1" style="vertical-align:top;">Tadalafil</td><td headers="hd_h_Tadalafil.T1_1_1_1_2" rowspan="1" colspan="1" style="vertical-align:top;">
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<a href="https://pubchem.ncbi.nlm.nih.gov/substance/135067956" ref="pagearea=body&targetsite=entrez&targetcat=link&targettype=pubchem">171596-29-5</a>
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</td><td headers="hd_h_Tadalafil.T1_1_1_1_3" rowspan="1" colspan="1" style="vertical-align:top;">C22-H19-N3-O4</td><td headers="hd_h_Tadalafil.T1_1_1_1_4" rowspan="1" colspan="1" style="vertical-align:top;">
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<div class="graphic"><img src="/books/NBK547910/bin/Tadalafil_Structure.jpg" alt="Tadalafil chemical structure" /></div>
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</td></tr></tbody></table></div></div></div><div id="bk_toc_contnr"></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/NBK547910/?report=reader">PubReader</a></li><li><a href="/books/NBK547910/?report=printable">Print View</a></li><li><a data-jig="ncbidialog" href="#_ncbi_dlg_citbx_NBK547910" data-jigconfig="width:400,modal:true">Cite this Page</a><div id="_ncbi_dlg_citbx_NBK547910" style="display:none" title="Cite this Page"><div class="bk_tt">LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012-. Tadalafil. 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<a href="https://www.ncbi.nlm.nih.gov/sites/entrez?cmd=search&db=pubmed&pubmedfilters=true&term=tadalafil+AND+Human%5BMH%5D+AND+(jaundice/CI+OR+bile+duct+diseases/CI+OR+liver/DE+OR+liver+diseases/CI)+AND+(%221900/1/1%22%5BEDat%5D%3A%222999/12/31%22%5BEDat%5D)" ref="pagearea=document-links&targetsite=external&targetcat=link&targettype=uri">Recent References on Tadalafil: from PubMed.gov</a>
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<a href="https://clinicaltrials.gov/ct2/results?term=tadalafil" ref="pagearea=document-links&targetsite=external&targetcat=link&targettype=uri">Trials on Tadalafil: from ClinicalTrials.gov</a>
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</li></ul></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=pcsubstance&DbFrom=books&Cmd=Link&LinkName=books_pcsubstance&IdsFromResult=4857830" ref="log$=recordlinks">PubChem Substance</a><div class="brieflinkpop offscreen_noflow">Related PubChem Substances</div></li></ul></div></div><div class="portlet"><div class="portlet_head"><div class="portlet_title"><h3><span>Similar articles in PubMed</span></h3></div><a name="Shutter" sid="1" href="#" class="portlet_shutter" title="Show/hide content" remembercollapsed="true" pgsec_name="PBooksDiscovery_RA" id="Shutter"></a></div><div class="portlet_content"><ul><li class="brieflinkpopper two_line"><a class="brieflinkpopperctrl" href="/pubmed/18614424" ref="ordinalpos=1&linkpos=1&log$=relatedarticles&logdbfrom=pubmed">Effectiveness of sildenafil citrate (Viagra) and tadalafil (Cialis) on sexual responses in Saudi men with erectile dysfunction in routine clinical practice.</a><span class="source">[Pak J Pharm Sci. 2008]</span><div class="brieflinkpop offscreen_noflow">Effectiveness of sildenafil citrate (Viagra) and tadalafil (Cialis) on sexual responses in Saudi men with erectile dysfunction in routine clinical practice.<div class="brieflinkpopdesc"><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="author">Ali ST. </em><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="cit">Pak J Pharm Sci. 2008 Jul; 21(3):275-81. </em></div></div></li><li class="brieflinkpopper two_line"><a class="brieflinkpopperctrl" href="/pubmed/9916601" ref="ordinalpos=1&linkpos=2&log$=relatedreviews&logdbfrom=pubmed"><span xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="invert">Review</span> Safety and efficacy of sildenafil citrate in the treatment of male erectile dysfunction.</a><span class="source">[Clin Ther. 1998]</span><div class="brieflinkpop offscreen_noflow"><span xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="invert">Review</span> Safety and efficacy of sildenafil citrate in the treatment of male erectile dysfunction.<div class="brieflinkpopdesc"><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="author">Goldenberg MM. </em><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="cit">Clin Ther. 1998 Nov-Dec; 20(6):1033-48. </em></div></div></li><li class="brieflinkpopper two_line"><a class="brieflinkpopperctrl" href="/pubmed/31643519" ref="ordinalpos=1&linkpos=3&log$=relatedreviews&logdbfrom=pubmed"><span xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="invert">Review</span> Phosphodiesterase Type 5 (PDE5) Inhibitors.</a><span class="source">[LiverTox: Clinical and Researc...]</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> Phosphodiesterase Type 5 (PDE5) Inhibitors.<div class="brieflinkpopdesc"><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="author">. </em><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="cit">LiverTox: Clinical and Research Information on Drug-Induced Liver Injury. 2012</em></div></div></li><li class="brieflinkpopper two_line"><a class="brieflinkpopperctrl" href="/pubmed/15115191" ref="ordinalpos=1&linkpos=4&log$=relatedreviews&logdbfrom=pubmed"><span xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="invert">Review</span> Phosphodiesterase type 5 inhibitor differentiation based on selectivity, pharmacokinetic, and efficacy profiles.</a><span class="source">[Clin Cardiol. 2004]</span><div class="brieflinkpop offscreen_noflow"><span xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="invert">Review</span> Phosphodiesterase type 5 inhibitor differentiation based on selectivity, pharmacokinetic, and efficacy profiles.<div class="brieflinkpopdesc"><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="author">Seftel AD. </em><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="cit">Clin Cardiol. 2004 Apr; 27(4 Suppl 1):I14-19. </em></div></div></li><li class="brieflinkpopper two_line"><a class="brieflinkpopperctrl" href="/pubmed/30548639" ref="ordinalpos=1&linkpos=5&log$=relatedarticles&logdbfrom=pubmed">Tadalafil: 15 years' journey in male erectile dysfunction and beyond.</a><span class="source">[Drug Dev Res. 2018]</span><div class="brieflinkpop offscreen_noflow">Tadalafil: 15 years' journey in male erectile dysfunction and beyond.<div class="brieflinkpopdesc"><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="author">Ahmed NS. </em><em xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" class="cit">Drug Dev Res. 2018 Dec 13; . Epub 2018 Dec 13.</em></div></div></li></ul><a class="seemore" href="/sites/entrez?db=pubmed&cmd=link&linkname=pubmed_pubmed_reviews&uid=31643246" ref="ordinalpos=1&log$=relatedreviews_seeall&logdbfrom=pubmed">See reviews...</a><a class="seemore" href="/sites/entrez?db=pubmed&cmd=link&linkname=pubmed_pubmed&uid=31643246" ref="ordinalpos=1&log$=relatedarticles_seeall&logdbfrom=pubmed">See all...</a></div></div><div class="portlet"><div class="portlet_head"><div class="portlet_title"><h3><span>Recent Activity</span></h3></div><a name="Shutter" sid="1" href="#" class="portlet_shutter" title="Show/hide content" remembercollapsed="true" pgsec_name="recent_activity" id="Shutter"></a></div><div class="portlet_content"><div xmlns:np="http://ncbi.gov/portal/XSLT/namespace" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" id="HTDisplay" class=""><div class="action"><a href="javascript:historyDisplayState('ClearHT')">Clear</a><a href="javascript:historyDisplayState('HTOff')" class="HTOn">Turn Off</a><a href="javascript:historyDisplayState('HTOn')" class="HTOff">Turn On</a></div><ul id="activity"><li class="ra_rcd ralinkpopper two_line"><a class="htb ralinkpopperctrl" ref="log$=activity&linkpos=1" href="/portal/utils/pageresolver.fcgi?recordid=67c8e1caab82281a804286a5">Tadalafil - LiverTox</a><div class="ralinkpop offscreen_noflow">Tadalafil - LiverTox<div class="brieflinkpopdesc"></div></div><div class="tertiary"></div></li><li class="ra_rcd ralinkpopper two_line"><a class="htb ralinkpopperctrl" ref="log$=activity&linkpos=2" href="/portal/utils/pageresolver.fcgi?recordid=67c8e1c9f4a390645e37a6ee">Tacrolimus - LiverTox</a><div class="ralinkpop offscreen_noflow">Tacrolimus - LiverTox<div class="brieflinkpopdesc"></div></div><div class="tertiary"></div></li><li class="ra_rcd ralinkpopper two_line"><a class="htb ralinkpopperctrl" ref="log$=activity&linkpos=3" href="/portal/utils/pageresolver.fcgi?recordid=67c8e1c8a68b6b5afc7a421f">Tacrine - LiverTox</a><div class="ralinkpop offscreen_noflow">Tacrine - LiverTox<div class="brieflinkpopdesc"></div></div><div class="tertiary"></div></li><li class="ra_rcd ralinkpopper two_line"><a class="htb ralinkpopperctrl" ref="log$=activity&linkpos=4" href="/portal/utils/pageresolver.fcgi?recordid=67c8e1c7f4a390645e379e13">Suvorexant - LiverTox</a><div class="ralinkpop offscreen_noflow">Suvorexant - LiverTox<div class="brieflinkpopdesc"></div></div><div class="tertiary"></div></li><li class="ra_rcd ralinkpopper two_line"><a class="htb ralinkpopperctrl" ref="log$=activity&linkpos=5" href="/portal/utils/pageresolver.fcgi?recordid=67c8e1c6b15b832ebc15a859">Sunitinib - LiverTox</a><div class="ralinkpop offscreen_noflow">Sunitinib - LiverTox<div class="brieflinkpopdesc"></div></div><div class="tertiary"></div></li></ul><p class="HTOn">Your browsing activity is empty.</p><p class="HTOff">Activity recording is turned off.</p><p id="turnOn" class="HTOff"><a href="javascript:historyDisplayState('HTOn')">Turn recording back on</a></p><a class="seemore" href="/sites/myncbi/recentactivity">See more...</a></div></div></div>
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