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</div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .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): AH-1058">AH-1058</span></caption><tbody><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><span typeof="mw:File"><a href="/wiki/File:AH-1058.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7e/AH-1058.svg/180px-AH-1058.svg.png" decoding="async" width="180" height="218" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7e/AH-1058.svg/270px-AH-1058.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7e/AH-1058.svg/360px-AH-1058.svg.png 2x" data-file-width="1135" data-file-height="1375" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</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>Investigational</li></ul></div> </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%;">1-[(<i>E</i>)-3-(3-Methoxy-2-nitrophenyl)prop-2-enyl]-4-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaenylidene)piperidine</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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=300347-11-9">300347-11-9</a></span> <br />228123-15-7 (<a href="/wiki/Hydrochloride" title="Hydrochloride">HCl</a>)</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/9804490">9804490</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/2AH1DI0W9U">2AH1DI0W9U</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/DTXSID801112852">DTXSID801112852</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q4651728#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>30</sub><span title="Hydrogen">H</span><sub>28</sub><span title="Nitrogen">N</span><sub>2</sub><span title="Oxygen">O</span><sub>3</sub></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="7002464565000000000♠"></span>464.565</span> 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=COC1%3DCC%3DCC%28%3DC1%5BN%2B%5D%28%3DO%29%5BO-%5D%29%2FC%3DC%2FCN2CCC%28%3DC3C4%3DCC%3DCC%3DC4C%3DCC5%3DCC%3DCC%3DC53%29CC2">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%;">COC1=CC=CC(=C1[N+](=O)[O-])/C=C/CN2CCC(=C3C4=CC=CC=C4C=CC5=CC=CC=C53)CC2</div></li></ul> </div></td></tr></tbody></table> <p><b>AH-1058</b> is a <a href="/wiki/Lipophilic" class="mw-redirect" title="Lipophilic">lipophilic</a> <a href="/wiki/Antiarrhythmic" class="mw-redirect" title="Antiarrhythmic">antiarrhythmic</a> <a href="/wiki/Calcium_channel_blocker" title="Calcium channel blocker">calcium channel blocker</a> synthesized by the Pharmaceutical Research Laboratories of <a href="/wiki/Ajinomoto" title="Ajinomoto">Ajinomoto Co., Inc</a> in <a href="/wiki/Kawasaki,_Kanagawa" title="Kawasaki, Kanagawa">Kawasaki</a>, <a href="/wiki/Japan" title="Japan">Japan</a>.<sup id="cite_ref-Takahara_1999_1-0" class="reference"><a href="#cite_note-Takahara_1999-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> It is derived from <a href="/wiki/Cyproheptadine" title="Cyproheptadine">cyproheptadine</a>, a compound with known antiserotonic, <a href="/wiki/Antihistaminic" class="mw-redirect" title="Antihistaminic">antihistaminic</a> and calcium channel blocking properties.<sup id="cite_ref-Takahara_1999_1-1" class="reference"><a href="#cite_note-Takahara_1999-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Kotake_1987_2-0" class="reference"><a href="#cite_note-Kotake_1987-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/IUPAC_nomenclature" class="mw-redirect" title="IUPAC nomenclature">IUPAC name</a> of AH-1058 is: 4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-[E-3-(3-methoxy-2-nitro) phenyl-2-propenyl]piperidine hydrochloride.<sup id="cite_ref-Takahara_2000b_3-0" class="reference"><a href="#cite_note-Takahara_2000b-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </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=AH-1058&action=edit&section=1" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>AH-1058 displays characteristics of Class IV antiarrhythmics (L-type calcium channel blockers). Class I antiarrhythmic (sodium channel blocker) characteristics have also been seen, but the effect AH-1058 has on sodium channels is variable and unknown.<sup id="cite_ref-Takahara_1999_1-2" class="reference"><a href="#cite_note-Takahara_1999-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Some proposed uses for AH-1058 include the treatment of <a href="/wiki/Angina_pectoris" class="mw-redirect" title="Angina pectoris">angina pectoris</a>, <a href="/wiki/Stenosis" title="Stenosis">stenosis</a> of the outflow tract from obstructive <a href="/wiki/Hypertrophic_cardiomyopathy" title="Hypertrophic cardiomyopathy">hypertrophic cardiomyopathy</a> and <a href="/wiki/Ventricular_arrhythmias" class="mw-redirect" title="Ventricular arrhythmias">ventricular arrhythmias</a>.<sup id="cite_ref-Takahara_1999_1-3" class="reference"><a href="#cite_note-Takahara_1999-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Takahara_2001c_4-0" class="reference"><a href="#cite_note-Takahara_2001c-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Treatment of these conditions (long term and short term) is possible due to the cardioselective nature of AH-1058 and the ability of AH-1058 to inhibit calcium channels and thus reduce cardiac contractility and <a href="/wiki/Energy_consumption" title="Energy consumption">energy consumption</a>.<sup id="cite_ref-Takahara_2000b_3-1" class="reference"><a href="#cite_note-Takahara_2000b-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Takahara_2001_5-0" class="reference"><a href="#cite_note-Takahara_2001-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Studies have compared AH-1058 to widely used and clinically available drugs such as <a href="/wiki/Verapamil" title="Verapamil">verapamil</a> (a Class IV antiarrhythmic drug)<sup id="cite_ref-Takahara_1999_1-4" class="reference"><a href="#cite_note-Takahara_1999-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Atenolol" title="Atenolol">atenolol</a> (a <a href="/wiki/Beta_blocker" title="Beta blocker">beta blocker</a>)<sup id="cite_ref-Ram_2010_6-0" class="reference"><a href="#cite_note-Ram_2010-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> to assess the efficacy of AH-1058. The effects of AH-1058 are slower to onset but longer-lasting than those of verapamil and atenolol.<sup id="cite_ref-Takahara_2000_7-0" class="reference"><a href="#cite_note-Takahara_2000-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Takahara_2001_5-1" class="reference"><a href="#cite_note-Takahara_2001-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> In addition, the minimal effects AH-1058 has on total <a href="/wiki/Peripheral_vascular_resistance" class="mw-redirect" title="Peripheral vascular resistance">peripheral vascular resistance</a> is an important advantage over <a href="/wiki/Atenolol" title="Atenolol">atenolol</a> and <a href="/wiki/Verapamil" title="Verapamil">verapamil</a>, as these drugs can be taken long term for disease management.<sup id="cite_ref-Takahara_2001b_8-0" class="reference"><a href="#cite_note-Takahara_2001b-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Lastly AH-1058 displays a greater selectivity for cardiac tissue over verapamil and atenolol with the same level of potency as verapamil in vitro.<sup id="cite_ref-Takahara_2001b_8-1" class="reference"><a href="#cite_note-Takahara_2001b-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Dohmoto_2003_9-0" class="reference"><a href="#cite_note-Dohmoto_2003-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> AH-1058 studies have been limited to <a href="/wiki/In_vitro" title="In vitro">in vitro</a> and <a href="/wiki/In_vivo" title="In vivo">in vivo</a> canine and guinea-pig models,<sup id="cite_ref-Takahara_2000b_3-2" class="reference"><a href="#cite_note-Takahara_2000b-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> with a greater potency displayed in vitro than in vivo.<sup id="cite_ref-Takahara_2000_7-1" class="reference"><a href="#cite_note-Takahara_2000-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Along with decreased potency in vivo, blood levels do not correlate with AH-1058 activity.<sup id="cite_ref-Takahara_2001b_8-2" class="reference"><a href="#cite_note-Takahara_2001b-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</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=AH-1058&action=edit&section=2" title="Edit section: Pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Mechanism_of_action">Mechanism of action</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=AH-1058&action=edit&section=3" title="Edit section: Mechanism of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>AH-1058 is a cardioselective L-type calcium channel blocker.<sup id="cite_ref-Takahara_1999_1-5" class="reference"><a href="#cite_note-Takahara_1999-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Takahara_2000b_3-3" class="reference"><a href="#cite_note-Takahara_2000b-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Tanaka_1999_10-0" class="reference"><a href="#cite_note-Tanaka_1999-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> AH-1058 binds to the same sites on the alpha-1 subunit of <a href="/wiki/L-type_calcium_channels" class="mw-redirect" title="L-type calcium channels">L-type calcium channels</a> as <a href="/wiki/Phenylalkylamines" class="mw-redirect" title="Phenylalkylamines">phenylalkylamines</a> (ex. verapamil) and <a href="/wiki/Benzothiazepine" class="mw-redirect" title="Benzothiazepine">benzothiazepines</a>; both of which are well known calcium channel blockers.<sup id="cite_ref-Takahara_2001_5-2" class="reference"><a href="#cite_note-Takahara_2001-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> These sites on the alpha-1 subunit differ from the active site of the calcium channel, meaning AH-1058 binds L-type calcium channels <a href="/wiki/Allosterically" class="mw-redirect" title="Allosterically">allosterically</a> to alter activity.<sup id="cite_ref-Takahara_2001_5-3" class="reference"><a href="#cite_note-Takahara_2001-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> In addition AH-1058 appears to interact with multiple states of L-type calcium channels (i.e. resting and inactive) to suppress calcium currents.<sup id="cite_ref-Takahara_1999_1-6" class="reference"><a href="#cite_note-Takahara_1999-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> A minor effect on sodium channels at higher concentrations has also been seen, but these effects appear to vary between species.<sup id="cite_ref-Takahara_1999_1-7" class="reference"><a href="#cite_note-Takahara_1999-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Mode_of_action">Mode of action</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=AH-1058&action=edit&section=4" title="Edit section: Mode of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The calcium blocking activity of AH-1058 can decrease ventricular <a href="/wiki/Contractility" title="Contractility">contractility</a>, <a href="/wiki/Heart_rate" title="Heart rate">heart rate</a>, and <a href="/wiki/Electrical_conductance" class="mw-redirect" title="Electrical conductance">conductance</a> through the <a href="/wiki/Atrioventricular_node" title="Atrioventricular node">atrioventricular node</a>.<sup id="cite_ref-Takahara_1999_1-8" class="reference"><a href="#cite_note-Takahara_1999-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Takahara_2000b_3-4" class="reference"><a href="#cite_note-Takahara_2000b-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Takahara_2000_7-2" class="reference"><a href="#cite_note-Takahara_2000-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> In addition AH-1058 has been shown to decrease <a href="/wiki/Systolic_blood_pressure" class="mw-redirect" title="Systolic blood pressure">systolic blood pressure</a> while minimally affecting total <a href="/wiki/Peripheral_vascular_resistance" class="mw-redirect" title="Peripheral vascular resistance">peripheral vascular resistance</a> and leaving <a href="/wiki/Diastolic_blood_pressure" class="mw-redirect" title="Diastolic blood pressure">diastolic blood pressure</a> unaffected.<sup id="cite_ref-Takahara_2001b_8-3" class="reference"><a href="#cite_note-Takahara_2001b-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> The order of the potency of the effects AH-1058 has on the <a href="/wiki/Cardiovascular_system" class="mw-redirect" title="Cardiovascular system">cardiovascular system</a> is: ventricular contraction > coronary blood flow >> atrioventricular conduction > sinoatrial automaticity (level of sinoatrial self-activation).<sup id="cite_ref-Takahara_2000_7-3" class="reference"><a href="#cite_note-Takahara_2000-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</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=AH-1058&action=edit&section=5" 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-Takahara_1999-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Takahara_1999_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Takahara_1999_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Takahara_1999_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Takahara_1999_1-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Takahara_1999_1-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Takahara_1999_1-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-Takahara_1999_1-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-Takahara_1999_1-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-Takahara_1999_1-8"><sup><i><b>i</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="CITEREFTakaharaUneyamaSasakiUeda1999" class="citation journal cs1">Takahara A, Uneyama H, Sasaki N, Ueda H, Dohmoto H, Shoji M, Hara Y, Nakaya H, Yoshimoto R (April 1999). <a rel="nofollow" class="external text" href="https://doi.org/10.1097%2F00005344-199904000-00016">"Effects of AH-1058, a new antiarrhythmic drug, on experimental arrhythmias and cardiac membrane currents"</a>. <i>Journal of Cardiovascular Pharmacology</i>. <b>33</b> (4): 625–32. <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/10.1097%2F00005344-199904000-00016">10.1097/00005344-199904000-00016</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/10218734">10218734</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Cardiovascular+Pharmacology&rft.atitle=Effects+of+AH-1058%2C+a+new+antiarrhythmic+drug%2C+on+experimental+arrhythmias+and+cardiac+membrane+currents&rft.volume=33&rft.issue=4&rft.pages=625-32&rft.date=1999-04&rft_id=info%3Adoi%2F10.1097%2F00005344-199904000-00016&rft_id=info%3Apmid%2F10218734&rft.aulast=Takahara&rft.aufirst=A&rft.au=Uneyama%2C+H&rft.au=Sasaki%2C+N&rft.au=Ueda%2C+H&rft.au=Dohmoto%2C+H&rft.au=Shoji%2C+M&rft.au=Hara%2C+Y&rft.au=Nakaya%2C+H&rft.au=Yoshimoto%2C+R&rft_id=https%3A%2F%2Fdoi.org%2F10.1097%252F00005344-199904000-00016&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAH-1058" class="Z3988"></span></span> </li> <li id="cite_note-Kotake_1987-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-Kotake_1987_2-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKotakeSaitohOginoHirai1987" class="citation journal cs1">Kotake H, Saitoh M, Ogino K, Hirai S, Matsuoka S, Hasegawa J, Mashiba H (July 1987). "On the ionic mechanism of cyproheptadine-induced bradycardia in a rabbit sinoatrial node preparation". <i>European Journal of Pharmacology</i>. <b>139</b> (3): 307–13. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0014-2999%2887%2990588-7">10.1016/0014-2999(87)90588-7</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/3666007">3666007</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=European+Journal+of+Pharmacology&rft.atitle=On+the+ionic+mechanism+of+cyproheptadine-induced+bradycardia+in+a+rabbit+sinoatrial+node+preparation&rft.volume=139&rft.issue=3&rft.pages=307-13&rft.date=1987-07&rft_id=info%3Adoi%2F10.1016%2F0014-2999%2887%2990588-7&rft_id=info%3Apmid%2F3666007&rft.aulast=Kotake&rft.aufirst=H&rft.au=Saitoh%2C+M&rft.au=Ogino%2C+K&rft.au=Hirai%2C+S&rft.au=Matsuoka%2C+S&rft.au=Hasegawa%2C+J&rft.au=Mashiba%2C+H&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAH-1058" class="Z3988"></span></span> </li> <li id="cite_note-Takahara_2000b-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-Takahara_2000b_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Takahara_2000b_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Takahara_2000b_3-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Takahara_2000b_3-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Takahara_2000b_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="CITEREFTakaharaSugiyamaDohmotoYoshimoto2000" class="citation journal cs1">Takahara A, Sugiyama A, Dohmoto H, Yoshimoto R, Hashimoto K (June 2000). <a rel="nofollow" class="external text" href="https://doi.org/10.1254%2Fjjp.83.107">"Electrophysiological and cardiohemodynamic effects of AH-1058, a new type calcium channel blocker, assessed by the in vivo canine model"</a>. <i>Japanese Journal of Pharmacology</i>. <b>83</b> (2): 107–12. <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/10.1254%2Fjjp.83.107">10.1254/jjp.83.107</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/10928322">10928322</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Japanese+Journal+of+Pharmacology&rft.atitle=Electrophysiological+and+cardiohemodynamic+effects+of+AH-1058%2C+a+new+type+calcium+channel+blocker%2C+assessed+by+the+in+vivo+canine+model&rft.volume=83&rft.issue=2&rft.pages=107-12&rft.date=2000-06&rft_id=info%3Adoi%2F10.1254%2Fjjp.83.107&rft_id=info%3Apmid%2F10928322&rft.aulast=Takahara&rft.aufirst=A&rft.au=Sugiyama%2C+A&rft.au=Dohmoto%2C+H&rft.au=Yoshimoto%2C+R&rft.au=Hashimoto%2C+K&rft_id=https%3A%2F%2Fdoi.org%2F10.1254%252Fjjp.83.107&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAH-1058" class="Z3988"></span></span> </li> <li id="cite_note-Takahara_2001c-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-Takahara_2001c_4-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTakaharaDohmotoYoshimotoSugiyama2001" class="citation journal cs1">Takahara A, Dohmoto H, Yoshimoto R, Sugiyama A, Hashimoto K (February 2001). 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title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Pharmacological+Sciences&rft.atitle=Cardiac+Ca%282%2B%29+channel-blocking+effects+of+the+cyproheptadine+derivative+AH-1058+in+isolated+guinea+pig+cardiomyocytes&rft.volume=91&rft.issue=2&rft.pages=163-6&rft.date=2003-02&rft_id=info%3Adoi%2F10.1254%2Fjphs.91.163&rft_id=info%3Apmid%2F12686762&rft.aulast=Dohmoto&rft.aufirst=H&rft.au=Takahara%2C+A&rft.au=Uneyama%2C+H&rft.au=Yoshimoto%2C+R&rft_id=https%3A%2F%2Fdoi.org%2F10.1254%252Fjphs.91.163&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAH-1058" class="Z3988"></span></span> </li> <li id="cite_note-Tanaka_1999-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-Tanaka_1999_10-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTanakaIchikawaMatsuiOkazaki1999" class="citation journal cs1">Tanaka H, Ichikawa T, Matsui S, Okazaki K, 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"Calcium channel antagonistic effects of AH-1058, a novel antiarrhythmic drug, on guinea-pig myocardium". <i>Research Communications in Molecular Pathology and Pharmacology</i>. <b>104</b> (1): 13–21. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/10604274">10604274</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Research+Communications+in+Molecular+Pathology+and+Pharmacology&rft.atitle=Calcium+channel+antagonistic+effects+of+AH-1058%2C+a+novel+antiarrhythmic+drug%2C+on+guinea-pig+myocardium&rft.volume=104&rft.issue=1&rft.pages=13-21&rft.date=1999&rft_id=info%3Apmid%2F10604274&rft.aulast=Tanaka&rft.aufirst=H&rft.au=Ichikawa%2C+T&rft.au=Matsui%2C+S&rft.au=Okazaki%2C+K&rft.au=Masumiya%2C+H&rft.au=Kawanishi%2C+T&rft.au=Shigenobu%2C+K&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAH-1058" class="Z3988"></span></span> </li> </ol></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=AH-1058&oldid=1136297029">https://en.wikipedia.org/w/index.php?title=AH-1058&oldid=1136297029</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Calcium_channel_blockers" title="Category:Calcium channel blockers">Calcium channel blockers</a></li><li><a href="/wiki/Category:Antiarrhythmic_agents" title="Category:Antiarrhythmic agents">Antiarrhythmic agents</a></li><li><a href="/wiki/Category:Dibenzocycloheptenes" title="Category:Dibenzocycloheptenes">Dibenzocycloheptenes</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_matches_Wikidata" title="Category:Short description matches Wikidata">Short description matches Wikidata</a></li><li><a href="/wiki/Category:Drugs_with_non-standard_legal_status" title="Category:Drugs with non-standard legal status">Drugs with non-standard legal status</a></li><li><a href="/wiki/Category:Articles_without_EBI_source" title="Category:Articles without EBI source">Articles without EBI source</a></li><li><a href="/wiki/Category:Chemical_pages_without_ChemSpiderID" title="Category:Chemical pages without ChemSpiderID">Chemical pages without ChemSpiderID</a></li><li><a href="/wiki/Category:Chemical_pages_without_DrugBank_identifier" title="Category:Chemical pages without DrugBank identifier">Chemical pages without DrugBank identifier</a></li><li><a href="/wiki/Category:Articles_without_KEGG_source" title="Category:Articles without KEGG source">Articles without KEGG source</a></li><li><a href="/wiki/Category:Articles_without_InChI_source" title="Category:Articles without InChI source">Articles without InChI source</a></li><li><a href="/wiki/Category:Drugs_missing_an_ATC_code" title="Category:Drugs missing an ATC code">Drugs missing an ATC code</a></li><li><a href="/wiki/Category:Articles_containing_unverified_chemical_infoboxes" title="Category:Articles containing unverified chemical infoboxes">Articles containing unverified chemical infoboxes</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 29 January 2023, at 17:53<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. 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