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Moguisteine - Wikipedia

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.dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}</style> <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): Moguisteine">Moguisteine</span></caption><tbody><tr><td colspan="2" class="infobox-image"><span class="mw-default-size dark_mode_safe" typeof="mw:File/Frameless"><a href="/wiki/File:Moguisteine_skeletal.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/41/Moguisteine_skeletal.png/220px-Moguisteine_skeletal.png" decoding="async" width="220" height="183" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/41/Moguisteine_skeletal.png/330px-Moguisteine_skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/41/Moguisteine_skeletal.png/440px-Moguisteine_skeletal.png 2x" data-file-width="1022" data-file-height="848" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">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%;">Ethyl 3-{2-[(2-methoxyphenoxy)methyl]-1,3-thiazolidin-3-yl}-3-oxopropanoate</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=119637-67-1">119637-67-1</a></span><sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></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/65935">65935</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.59340.html">59340</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/6Y556547YY">6Y556547YY</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/chembl/explore/compound/ChEMBL146980">ChEMBL146980</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/DTXSID00869634">DTXSID00869634</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q27265705#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;color:inherit;">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>16</sub><span title="Hydrogen">H</span><sub>21</sub><span title="Nitrogen">N</span><span title="Oxygen">O</span><sub>5</sub><span title="Sulfur">S</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="7002339410000000000♠"></span>339.41</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=CCOC%28%3DO%29CC%28%3DO%29N1CCSC1COC2%3DCC%3DCC%3DC2OC">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%;">CCOC(=O)CC(=O)N1CCSC1COC2=CC=CC=C2OC</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/C16H21NO5S/c1-3-21-16(19)10-14(18)17-8-9-23-15(17)11-22-13-7-5-4-6-12(13)20-2/h4-7,15H,3,8-11H2,1-2H3</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:WSYVIAQNTFPTBI-UHFFFAOYSA-N</div></li></ul> </div></td></tr></tbody></table> <p><b>Moguisteine</b> is a non-narcotic, peripherally acting <a href="/wiki/Antitussive" class="mw-redirect" title="Antitussive">antitussive</a>.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup> In a small double-blind, randomized controlled trial, 200 mg of moguisteine suspension taken 3 times daily significantly reduced the frequency of coughing in patients with <a href="/wiki/Chronic_obstructive_pulmonary_disease" title="Chronic obstructive pulmonary disease">COPD</a>, compared to placebo.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">&#91;</span>2<span class="cite-bracket">&#93;</span></a></sup> It has also been studied in small trials in comparison to codeine<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup> and dextromethorphan,<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">&#91;</span>4<span class="cite-bracket">&#93;</span></a></sup> and has similar efficacy to both. It has not been approved for use in the United States.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> </p><p>It was discovered by searching for <a href="/wiki/Expectorant" class="mw-redirect" title="Expectorant">expectorants</a> of the <a href="/wiki/Thiazolidine" title="Thiazolidine">thiazolidine</a> class, when compounds with a cough suppressant effect were accidentally found and moguisteine was selected as the most effective and safest representative of the class.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup> Its mechanism of action may be the activation of <a href="/wiki/ATP-sensitive_potassium_channel" title="ATP-sensitive potassium channel">ATP-sensitive potassium channels</a>.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">&#91;</span>7<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=Moguisteine&amp;action=edit&amp;section=1" 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-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></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="CITEREFGallicoBorghiDalla_RosaCeserani1994" class="citation journal cs1">Gallico L, Borghi A, Dalla Rosa C, 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navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Cough_and_cold_preparations" title="Template:Cough and cold preparations"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Cough_and_cold_preparations" title="Template talk:Cough and cold preparations"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Cough_and_cold_preparations" title="Special:EditPage/Template:Cough and cold preparations"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Cough_and_cold_preparations_(R05)477" style="font-size:114%;margin:0 4em"><a href="/wiki/Cough_medicine" class="mw-redirect" title="Cough medicine">Cough and cold preparations</a> (<a href="/wiki/ATC_code_R05" title="ATC code R05">R05</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mucolytic_agent" class="mw-redirect" title="Mucolytic agent">Expectorants</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Althaea_(plant)" title="Althaea (plant)">Althea root</a></li> <li><a href="/wiki/Ammonium_chloride" title="Ammonium chloride">Ammonium chloride</a></li> <li><a href="/wiki/Antimony_pentasulfide" title="Antimony pentasulfide">Antimony pentasulfide</a></li> <li><a href="/wiki/Cineole" class="mw-redirect" title="Cineole">Cineole</a></li> <li><a href="/wiki/Creosote" title="Creosote">Creosote</a></li> <li><a href="/wiki/Guaiacolsulfonate" class="mw-redirect" title="Guaiacolsulfonate">Guaiacolsulfonate</a></li> <li><a href="/wiki/Guaifenesin" title="Guaifenesin">Guaifenesin</a> (<a href="/wiki/Guaifenesin/codeine" title="Guaifenesin/codeine">+codeine</a>, <a href="/wiki/Hydrocodone/guaifenesin" title="Hydrocodone/guaifenesin">+hydrocodone</a>, <a href="/wiki/Oxomemazine/guaifenesin" title="Oxomemazine/guaifenesin">+oxomemazine</a>)</li> <li><a href="/wiki/Hedera_helix" title="Hedera helix">Hederae helicis folium</a></li> <li><a href="/wiki/Carapichea_ipecacuanha" title="Carapichea ipecacuanha">Ipecacuanha</a> (<a href="/wiki/Syrup_of_ipecac" title="Syrup of ipecac">Syrup of ipecac</a>)</li> <li><a href="/wiki/Levoverbenone" title="Levoverbenone">Levoverbenone</a></li> <li><a href="/wiki/Potassium_iodide" title="Potassium iodide">Potassium iodide</a></li> <li><a href="/wiki/Polygala_senega" class="mw-redirect" title="Polygala senega">Senega</a></li> <li><a href="/wiki/Tyloxapol" title="Tyloxapol">Tyloxapol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mucolytic_agent" class="mw-redirect" title="Mucolytic agent">Mucolytics</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetylcysteine" title="Acetylcysteine">Acetylcysteine</a><sup>#</sup></li> <li><a href="/wiki/Ambroxol" title="Ambroxol">Ambroxol</a></li> <li><a href="/wiki/Bromhexine" title="Bromhexine">Bromhexine</a></li> <li><a href="/wiki/Carbocisteine" title="Carbocisteine">Carbocisteine</a></li> <li><a href="/w/index.php?title=Dembrexine_hydrochloride&amp;action=edit&amp;redlink=1" class="new" title="Dembrexine hydrochloride (page does not exist)">Dembrexine hydrochloride</a></li> <li><a href="/wiki/Domiodol" title="Domiodol">Domiodol</a></li> <li><a href="/wiki/Dornase_alfa" title="Dornase alfa">Dornase alfa</a></li> <li><a href="/wiki/Eprazinone" title="Eprazinone">Eprazinone</a></li> <li><a href="/wiki/Erdosteine" title="Erdosteine">Erdosteine</a></li> <li><a href="/wiki/Letosteine" title="Letosteine">Letosteine</a></li> <li><a href="/wiki/Mannitol" title="Mannitol">Mannitol</a></li> <li><a href="/wiki/Mesna" title="Mesna">Mesna</a></li> <li><a href="/wiki/Neltenexine" title="Neltenexine">Neltenexine</a></li> <li><a href="/wiki/Sobrerol" title="Sobrerol">Sobrerol</a></li> <li><a href="/wiki/Stepronin" title="Stepronin">Stepronin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cough_suppressant" class="mw-redirect" title="Cough suppressant">Cough suppressants</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Opium" title="Opium">Opium</a> alkaloids,<br /><a href="/wiki/Opioid" title="Opioid">opioids</a>,<br />and derivatives</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetyldihydrocodeine" title="Acetyldihydrocodeine">Acetyldihydrocodeine</a></li> <li><a href="/wiki/Benzylmorphine" title="Benzylmorphine">Benzylmorphine</a></li> <li><a href="/wiki/Butorphanol" title="Butorphanol">Butorphanol</a></li> <li><a href="/wiki/Codeine" title="Codeine">Codeine</a><sup>#</sup> (<a href="/wiki/Guaifenesin/codeine" title="Guaifenesin/codeine">+guaifenesin</a>)</li> <li><a href="/wiki/Dextromethorphan" title="Dextromethorphan">Dextromethorphan</a></li> <li><a href="/wiki/Dihydrocodeine" title="Dihydrocodeine">Dihydrocodeine</a></li> <li><a href="/wiki/Dimemorfan" title="Dimemorfan">Dimemorfan</a></li> <li><a href="/wiki/Ethylmorphine" title="Ethylmorphine">Ethylmorphine</a></li> <li><a href="/wiki/Heroin" title="Heroin">Heroin</a></li> <li><a href="/wiki/Hydrocodone" title="Hydrocodone">Hydrocodone</a> (<a href="/wiki/Hydrocodone/guaifenesin" title="Hydrocodone/guaifenesin">+guaifenesin</a>, <a href="/wiki/Hydrocodone/homatropine" title="Hydrocodone/homatropine">+homatropine</a>)</li> <li><a href="/wiki/Hydromorphone" title="Hydromorphone">Hydromorphone</a></li> <li><a href="/wiki/Laudanum" title="Laudanum">Laudanum</a></li> <li><a href="/wiki/Levomethadone" title="Levomethadone">Levomethadone</a></li> <li><a href="/wiki/Levopropoxyphene" title="Levopropoxyphene">Levopropoxyphene</a></li> <li><a href="/wiki/Methadone" title="Methadone">Methadone</a></li> <li><a href="/wiki/Nicocodeine" title="Nicocodeine">Nicocodeine</a></li> <li><a href="/wiki/Nicodicodeine" class="mw-redirect" title="Nicodicodeine">Nicodicodeine</a></li> <li><a href="/wiki/Normethadone" title="Normethadone">Normethadone</a></li> <li><a href="/wiki/Noscapine" title="Noscapine">Noscapine</a></li> <li><a href="/wiki/Pholcodine" title="Pholcodine">Pholcodine</a></li> <li><a href="/wiki/Dihydrocodeinone_enol_acetate" class="mw-redirect" title="Dihydrocodeinone enol acetate">Thebacon</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alloclamide" title="Alloclamide">Alloclamide</a></li> <li><a href="/wiki/Benproperine" title="Benproperine">Benproperine</a></li> <li><a href="/wiki/Benzonatate" title="Benzonatate">Benzonatate</a></li> <li><a href="/wiki/Bibenzonium_bromide" title="Bibenzonium bromide">Bibenzonium bromide</a></li> <li><a href="/wiki/Butamirate" title="Butamirate">Butamirate</a></li> <li><a href="/wiki/Clobutinol" title="Clobutinol">Clobutinol</a></li> <li><a href="/wiki/Clofedanol" title="Clofedanol">Clofedanol</a></li> <li><a href="/wiki/Cloperastine" title="Cloperastine">Cloperastine</a></li> <li><a href="/wiki/Dibunate" title="Dibunate">Dibunate</a></li> <li><a href="/wiki/Dimethoxanate" title="Dimethoxanate">Dimethoxanate</a></li> <li><a href="/wiki/Diphenhydramine" title="Diphenhydramine">Diphenhydramine</a></li> <li><a href="/wiki/Dropropizine" title="Dropropizine">Dropropizine</a></li> <li><a href="/wiki/Droxypropine" title="Droxypropine">Droxypropine</a></li> <li><a href="/wiki/Fedrilate" title="Fedrilate">Fedrilate</a></li> <li><a href="/wiki/Fominoben" title="Fominoben">Fominoben</a></li> <li><a href="/wiki/Gefapixant" title="Gefapixant">Gefapixant</a></li> <li><a href="/wiki/Glaucine" title="Glaucine">Glaucine</a></li> <li><a href="/wiki/Isoaminile" title="Isoaminile">Isoaminile</a></li> <li><a href="/wiki/Levodropropizine" title="Levodropropizine">Levodropropizine</a></li> <li><a href="/wiki/Meprotixol" title="Meprotixol">Meprotixol</a></li> <li><a class="mw-selflink selflink">Moguisteine</a></li> <li><a href="/wiki/Morclofone" title="Morclofone">Morclofone</a></li> <li><a href="/wiki/Nepinalone" title="Nepinalone">Nepinalone</a></li> <li><a href="/wiki/Oxeladin" title="Oxeladin">Oxeladin</a></li> <li><a href="/wiki/Oxolamine" title="Oxolamine">Oxolamine</a></li> <li><a href="/wiki/Pentoxyverine" title="Pentoxyverine">Pentoxyverine</a></li> <li><a href="/wiki/Pipazetate" title="Pipazetate">Pipazetate</a></li> <li><a href="/wiki/Piperidione" title="Piperidione">Piperidione</a></li> <li><a href="/wiki/Prenoxdiazine" title="Prenoxdiazine">Prenoxdiazine</a></li> <li><a href="/wiki/Tipepidine" title="Tipepidine">Tipepidine</a></li> <li><a href="/wiki/Zipeprol" title="Zipeprol">Zipeprol</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="padding: 0px;"><div><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></div></td></tr></tbody></table></div> <!-- NewPP limit report Parsed by mw‐api‐ext.eqiad.main‐58bb4f8ccf‐dn6sd Cached time: 20250215041832 Cache expiry: 2592000 Reduced expiry: false Complications: [vary‐revision‐sha1] CPU time usage: 0.406 seconds Real time usage: 0.590 seconds Preprocessor visited node count: 4356/1000000 Post‐expand include size: 78936/2097152 bytes Template argument size: 3722/2097152 bytes Highest expansion depth: 18/100 Expensive parser function count: 2/500 Unstrip recursion depth: 1/20 Unstrip post‐expand size: 43625/5000000 bytes Lua time usage: 0.209/10.000 seconds Lua memory usage: 7168715/52428800 bytes Number of Wikibase entities loaded: 1/400 --> <!-- Transclusion expansion time report (%,ms,calls,template) 100.00% 542.546 1 -total 50.60% 274.530 1 Template:Drugbox 37.44% 203.117 1 Template:Infobox 24.03% 130.372 1 Template:Reflist 21.42% 116.229 7 Template:Cite_journal 13.92% 75.497 17 Template:Unbulleted_list 13.64% 74.006 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