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Regrelor - Wikipedia

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.infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Regrelor">Regrelor</span></caption><tbody><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><span class="mw-default-size" typeof="mw:File/Frameless"><a href="/wiki/File:Regrelor_in_ChemDraw_16.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/36/Regrelor_in_ChemDraw_16.svg/220px-Regrelor_in_ChemDraw_16.svg.png" decoding="async" width="220" height="180" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/36/Regrelor_in_ChemDraw_16.svg/330px-Regrelor_in_ChemDraw_16.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/36/Regrelor_in_ChemDraw_16.svg/440px-Regrelor_in_ChemDraw_16.svg.png 2x" data-file-width="512" data-file-height="418" /></a></span></td></tr><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><span class="mw-default-size" typeof="mw:File/Frameless"><a href="/wiki/File:RegrelorSpin.gif" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/RegrelorSpin.gif/220px-RegrelorSpin.gif" decoding="async" width="220" height="154" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/RegrelorSpin.gif/330px-RegrelorSpin.gif 1.5x, //upload.wikimedia.org/wikipedia/commons/5/58/RegrelorSpin.gif 2x" data-file-width="370" data-file-height="259" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_class" title="Drug class">Drug class</a></th><td class="infobox-data"><a href="/wiki/Antiplatelet_drug" title="Antiplatelet drug">antiplatelet drug</a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">[(2S,3aR,4R,6R,6aR)-6-[6-(ethylcarbamoylamino)purin-9-yl]-2-[(E)-2-phenylethenyl]-3a,4,6,6a-tetrahydrofuro[4,3-d][1,3]dioxol-4-yl]methyl dihydrogen phosphate</div></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></th><td class="infobox-data"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=787548-03-2">787548-03-2</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <span style="font-weight:normal"><abbr title="Compound ID">CID</abbr></span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/11273179">11273179</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.9448187.html">9448187</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/Q6C8TY6SW1">Q6C8TY6SW1</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/KEGG" title="KEGG">KEGG</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D08983">D08983</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL261244">ChEMBL261244</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID80229272">DTXSID80229272</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q27088528#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data"><span title="Carbon">C</span><sub>22</sub><span title="Hydrogen">H</span><sub>25</sub><span title="Nitrogen">N</span><sub>6</sub><span title="Oxygen">O</span><sub>8</sub><span title="Phosphorus">P</span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data"><span class="nowrap"><span data-sort-value="7002532450000000000♠"></span>532.450</span>&#160;g·mol<sup>−1</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CCNC%28%3DO%29NC1%3DNC%3DNC2%3DC1N%3DCN2C3C4C%28C%28O3%29COP%28%3DO%29%28O%29O%29OC%28O4%29C%3DCC5%3DCC%3DCC%3DC5">Interactive image</a></span></li></ul></div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">CCNC(=O)NC1=NC=NC2=C1N=CN2C3C4C(C(O3)COP(=O)(O)O)OC(O4)C=CC5=CC=CC=C5</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/C22H25N6O8P/c1-2-23-22(29)27-19-16-20(25-11-24-19)28(12-26-16)21-18-17(14(34-21)10-33-37(30,31)32)35-15(36-18)9-8-13-6-4-3-5-7-13/h3-9,11-12,14-15,17-18,21H,2,10H2,1H3,(H2,30,31,32)(H2,23,24,25,27,29)/b9-8+/t14-,15+,17-,18-,21-/m1/s1</div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:NXHAXEBZOXCDKD-XIXRRVGJSA-N</div></li></ul> </div></td></tr></tbody></table> <p><b>Regrelor</b> (also known as <b>INS50589</b>) is an experimental <a href="/wiki/Antiplatelet_drug" title="Antiplatelet drug">antiplatelet drug</a> that was under investigation by <a href="/wiki/Merck_%26_Co." title="Merck &amp; Co.">Merck Sharp and Dohme</a> in human <a href="/wiki/Clinical_trials" class="mw-redirect" title="Clinical trials">clinical trials</a>. Although it was initially found to be well tolerated in healthy subjects, safety concerns led to cessation of clinical trials. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Medical_uses">Medical uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Regrelor&amp;action=edit&amp;section=1" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Regrelor is an experimental drug. It is classified as an antiplatelet medication.<sup id="cite_ref-Moliterno_Lit_Review_1-0" class="reference"><a href="#cite_note-Moliterno_Lit_Review-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup> It was under investigation for use in <a href="/wiki/Thrombosis" title="Thrombosis">blood clotting</a> problems,<sup id="cite_ref-AdisInsight_2-0" class="reference"><a href="#cite_note-AdisInsight-2"><span class="cite-bracket">&#91;</span>2<span class="cite-bracket">&#93;</span></a></sup> as well as during <a href="/wiki/Coronary_artery_bypass_surgery" title="Coronary artery bypass surgery">coronary artery bypass surgery</a>.<sup id="cite_ref-MedChem_III_3-0" class="reference"><a href="#cite_note-MedChem_III-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Available_forms">Available forms</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Regrelor&amp;action=edit&amp;section=2" title="Edit section: Available forms"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Regrelor is available in an <a href="/wiki/Intravenous" class="mw-redirect" title="Intravenous">intravenous</a> formulation.<sup id="cite_ref-Moliterno_Lit_Review_1-1" class="reference"><a href="#cite_note-Moliterno_Lit_Review-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Regrelor&amp;action=edit&amp;section=3" title="Edit section: Pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Regrelor is classified as a <a href="/wiki/P2Y12" title="P2Y12">purinergic P2 receptor</a> (P2Y<sub>12</sub>) <a href="/wiki/Adenosine_diphosphate_receptor_inhibitor" title="Adenosine diphosphate receptor inhibitor">antagonist</a>.<sup id="cite_ref-PubChem_4-0" class="reference"><a href="#cite_note-PubChem-4"><span class="cite-bracket">&#91;</span>4<span class="cite-bracket">&#93;</span></a></sup> Other compounds in the same mechanistic class include <a href="/wiki/Clopidogrel" title="Clopidogrel">clopidogrel</a> and <a href="/wiki/Ticagrelor" title="Ticagrelor">ticagrelor</a>. It is characterized as a <a href="/wiki/Receptor_antagonist#Reversibility" title="Receptor antagonist">reversible</a>, <a href="/wiki/Competitive_antagonist" class="mw-redirect" title="Competitive antagonist">competitive</a> receptor antagonist.<sup id="cite_ref-Johnson_et_al_Phase1_5-0" class="reference"><a href="#cite_note-Johnson_et_al_Phase1-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> The <a href="/wiki/IC50" title="IC50">IC50</a> for antagonism of ADP-induced (P2Y<sub>12</sub>-mediated) platelet aggregation was 16 nM <i>in vitro</i>.<sup id="cite_ref-MedChem_III_3-1" class="reference"><a href="#cite_note-MedChem_III-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup> </p><p>Regrelor's <a href="/wiki/Primary_metabolite" title="Primary metabolite">primary metabolite</a> is called INS51088.<sup id="cite_ref-Johnson_et_al_Phase1_5-1" class="reference"><a href="#cite_note-Johnson_et_al_Phase1-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Regrelor&amp;action=edit&amp;section=4" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Regrelor is structurally similar to <a href="/wiki/Adenosine_monophosphate" title="Adenosine monophosphate">AMP</a>, just like <a href="/wiki/Ticagrelor" title="Ticagrelor">ticagrelor</a>.<sup id="cite_ref-MedChem_III_3-2" class="reference"><a href="#cite_note-MedChem_III-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup> Regrelor has 4 <a href="/wiki/Hydrogen_bond" title="Hydrogen bond">hydrogen bond</a> donors and 11 acceptors.<sup id="cite_ref-PubChem_4-1" class="reference"><a href="#cite_note-PubChem-4"><span class="cite-bracket">&#91;</span>4<span class="cite-bracket">&#93;</span></a></sup> It is produced as a di<a href="/wiki/Sodium" title="Sodium">sodium</a> salt.<sup id="cite_ref-pharmacodia_6-0" class="reference"><a href="#cite_note-pharmacodia-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup> The two <a href="/wiki/Sodium" title="Sodium">sodium</a> atoms bind the negatively charged <a href="/wiki/Phosphate" title="Phosphate">phosphate</a> moiety in solution.<sup id="cite_ref-MedChem_III_3-3" class="reference"><a href="#cite_note-MedChem_III-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Synthesis">Synthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Regrelor&amp;action=edit&amp;section=5" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Regrelor was synthesized from <a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">adenosine diphosphate</a> (ADP), an endogenous chemical involved in <a href="/wiki/Metabolism" title="Metabolism">metabolism</a>.<sup id="cite_ref-hyperphysics.phy-astr.gsu.edu_7-0" class="reference"><a href="#cite_note-hyperphysics.phy-astr.gsu.edu-7"><span class="cite-bracket">&#91;</span>7<span class="cite-bracket">&#93;</span></a></sup> The authors noted that the addition of a lipophilic moiety like <a href="/wiki/Cinnamaldehyde" title="Cinnamaldehyde">cinnamaldehyde</a> at the C-2' and C-3' positions, combined with ethylurea at N-6 on the <a href="/wiki/Adenine" title="Adenine">adenine</a> base, yielded regrelor.<sup id="cite_ref-Douglass_et_al_Synthesis_8-0" class="reference"><a href="#cite_note-Douglass_et_al_Synthesis-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Regrelor&amp;action=edit&amp;section=6" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Regrelor was developed around the same time as <a href="/wiki/Prasugrel" title="Prasugrel">prasugrel</a> and <a href="/wiki/Cangrelor" title="Cangrelor">cangrelor</a>.<sup id="cite_ref-Moliterno_Lit_Review_1-2" class="reference"><a href="#cite_note-Moliterno_Lit_Review-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup> After Inspire Pharmaceuticals initially developed the drug, it was purchased by Merck Sharp and Dohme.<sup id="cite_ref-pharmacodia_6-1" class="reference"><a href="#cite_note-pharmacodia-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Regrelor&amp;action=edit&amp;section=7" title="Edit section: Research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Pre-clinical_development" class="mw-redirect" title="Pre-clinical development">Pre-clinical experiments</a> in <a href="/wiki/Laboratory_rat" title="Laboratory rat">rats</a>, dogs, and <a href="/wiki/Animal_testing_on_non-human_primates" title="Animal testing on non-human primates">monkeys</a> found that the drug acted quickly to inhibit platelet aggregation, and that baseline function was restored quickly after discontinuation of treatment.<sup id="cite_ref-Johnson_et_al_Phase1_5-2" class="reference"><a href="#cite_note-Johnson_et_al_Phase1-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> </p><p>In a <a href="/wiki/Phase_1_clinical_trial" class="mw-redirect" title="Phase 1 clinical trial">phase 1 clinical trial</a> sponsored by Merck Sharp and Dohme Corporation, regrelor was well tolerated in healthy volunteers.<sup id="cite_ref-Phase1_clinicaltrials.gov_9-0" class="reference"><a href="#cite_note-Phase1_clinicaltrials.gov-9"><span class="cite-bracket">&#91;</span>9<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Johnson_et_al_Phase1_5-3" class="reference"><a href="#cite_note-Johnson_et_al_Phase1-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> In 2008, phase 2 trials were discontinued.<sup id="cite_ref-AdisInsight_2-1" class="reference"><a href="#cite_note-AdisInsight-2"><span class="cite-bracket">&#91;</span>2<span class="cite-bracket">&#93;</span></a></sup> It is believed that further development of the drug was ceased due to safety reasons.<sup id="cite_ref-pharmacodia_6-2" class="reference"><a href="#cite_note-pharmacodia-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup> In the trial, there was an increased risk of <a href="/wiki/Bleeding" title="Bleeding">bleeding</a> for patients on regrelor.<sup id="cite_ref-MedChem_III_3-4" class="reference"><a href="#cite_note-MedChem_III-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Regrelor&amp;action=edit&amp;section=8" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-Moliterno_Lit_Review-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Moliterno_Lit_Review_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Moliterno_Lit_Review_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Moliterno_Lit_Review_1-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFMoliterno2008" class="citation journal cs1 cs1-prop-long-vol">Moliterno DJ (December 2008). <a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1540-8183.2008.00409.x">"Advances in antiplatelet therapy for ACS and PCI"</a>. <i>Journal of Interventional Cardiology</i>. 21 Suppl 1 (Suppl 1): S18-24. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1540-8183.2008.00409.x">10.1111/j.1540-8183.2008.00409.x</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/19090933">19090933</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Journal+of+Interventional+Cardiology&amp;rft.atitle=Advances+in+antiplatelet+therapy+for+ACS+and+PCI&amp;rft.volume=21+Suppl+1&amp;rft.issue=Suppl+1&amp;rft.pages=S18-24&amp;rft.date=2008-12&amp;rft_id=info%3Adoi%2F10.1111%2Fj.1540-8183.2008.00409.x&amp;rft_id=info%3Apmid%2F19090933&amp;rft.aulast=Moliterno&amp;rft.aufirst=DJ&amp;rft_id=https%3A%2F%2Fdoi.org%2F10.1111%252Fj.1540-8183.2008.00409.x&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ARegrelor" class="Z3988"></span></span> </li> <li id="cite_note-AdisInsight-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-AdisInsight_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-AdisInsight_2-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://adisinsight.springer.com/drugs/800022230">"Regrelor"</a>. <i>Adis Insight</i>. Springer International Publishing AG<span class="reference-accessdate">. Retrieved <span class="nowrap">3 August</span> 2017</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=unknown&amp;rft.jtitle=Adis+Insight&amp;rft.atitle=Regrelor&amp;rft_id=http%3A%2F%2Fadisinsight.springer.com%2Fdrugs%2F800022230&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ARegrelor" class="Z3988"></span></span> </li> <li id="cite_note-MedChem_III-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-MedChem_III_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-MedChem_III_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-MedChem_III_3-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-MedChem_III_3-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-MedChem_III_3-4"><sup><i><b>e</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChackalamannilRotellaWard2017" class="citation book cs1">Chackalamannil S, Rotella D, Ward S (3 June 2017). <i>Comprehensive Medicinal Chemistry</i> (III&#160;ed.). 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