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<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:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Sodium_butyrate" title="Sodium butyrate">Sodium butyrate</a>.</div> <p class="mw-empty-elt"> </p> <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): Sodium phenylbutyrate">Sodium phenylbutyrate</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:Sodium_phenylbutyrate_Structural_Formula_V1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Sodium_phenylbutyrate_Structural_Formula_V1.svg/220px-Sodium_phenylbutyrate_Structural_Formula_V1.svg.png" decoding="async" width="220" height="75" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Sodium_phenylbutyrate_Structural_Formula_V1.svg/330px-Sodium_phenylbutyrate_Structural_Formula_V1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Sodium_phenylbutyrate_Structural_Formula_V1.svg/440px-Sodium_phenylbutyrate_Structural_Formula_V1.svg.png 2x" data-file-width="380" data-file-height="129" /></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_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Buphenyl, Pheburane, Ammonaps, others</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/American_Society_of_Health-System_Pharmacists" title="American Society of Health-System Pharmacists">AHFS</a>/<a href="/wiki/Drugs.com" title="Drugs.com">Drugs.com</a></th><td class="infobox-data"><span title="www.drugs.com"><a rel="nofollow" class="external text" href="https://www.drugs.com/cons/sodium_phenylbutyrate.html">Micromedex Detailed Consumer Information</a></span></td></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">License data</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><small><abbr class="country-name" title="United States">US</abbr></small> <a href="/wiki/DailyMed" title="DailyMed">DailyMed</a>: <span title="dailymed.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=all&query=Sodium+phenylbutyrate">Sodium phenylbutyrate</a></span></li></ul></div> </td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Pregnancy_category" title="Pregnancy category">Pregnancy<br />category</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li><small><abbr class="country-name" title="Australia">AU</abbr>:</small> B3</li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of<br />administration</a></th><td class="infobox-data"><a href="/wiki/By_mouth" class="mw-redirect" title="By mouth">By mouth</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a href="/wiki/ATC_code_A16" title="ATC code A16">A16AX03</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=A16AX03">WHO</a></span>) </li></ul></div></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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li><small><abbr class="country-name" title="Australia">AU</abbr>:</small> <a href="/wiki/Standard_for_the_Uniform_Scheduling_of_Medicines_and_Poisons#Schedule_4" title="Standard for the Uniform Scheduling of Medicines and Poisons">S4</a> (Prescription only)<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li> <li><small><abbr class="country-name" title="Canada">CA</abbr></small>: <a href="/wiki/Prescription_drug" title="Prescription drug"> ℞-only</a><sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></li> <li><small><abbr class="country-name" title="United States">US</abbr>:</small> <a href="/wiki/Prescription_drug" title="Prescription drug">℞-only</a><sup id="cite_ref-Buphenyl_FDA_label_4-0" class="reference"><a href="#cite_note-Buphenyl_FDA_label-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Olpruva_FDA_label_5-0" class="reference"><a href="#cite_note-Olpruva_FDA_label-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup></li> <li><small><abbr class="country-name" title="European Union">EU</abbr>:</small> Rx-only<sup id="cite_ref-Ammonaps_EPAR_6-0" class="reference"><a href="#cite_note-Ammonaps_EPAR-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup></li> <li>In general: ℞ (Prescription only)</li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a></th><td class="infobox-data"><a href="/wiki/Liver" title="Liver">Liver</a> and kidney to <a href="/wiki/Phenylacetic_acid" title="Phenylacetic acid">phenylacetic acid</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Biological_half-life" title="Biological half-life">Elimination <span class="nowrap">half-life</span></a></th><td class="infobox-data">0.8 hours (phenylbutyrate), 1.15-1.29 hours (phenylacetate)</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Excretion" title="Excretion">Excretion</a></th><td class="infobox-data">Urine (80-100% as phenylacetylglutamine)</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%;">Sodium 4-phenylbutanoate</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=1716-12-7">1716-12-7</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</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/5258">5258</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/DrugBank" title="DrugBank">DrugBank</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.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DBSALT002404">DBSALT002404</a></span><sup> <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/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.5068.html">5068</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></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/NT6K61736T">NT6K61736T</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/D05868">D05868</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEBI" title="ChEBI">ChEBI</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/chebi/searchId.do?chebiId=CHEBI:75316">CHEBI:75316</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></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/ChEMBL1746">ChEMBL1746</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></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/DTXSID7040948">DTXSID7040948</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q7553358#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 scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.130.318">100.130.318</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q7553358#P2566" 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></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>10</sub><span title="Hydrogen">H</span><sub>11</sub><span title="Sodium">Na</span><span title="Oxygen">O</span><sub>2</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="7002186186000000000♠"></span>186.186</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=%5BNa%2B%5D.%5BO-%5DC%28%3DO%29CCCC1%3DCC%3DCC%3DC1">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%;">[Na+].[O-]C(=O)CCCC1=CC=CC=C1</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/C10H12O2.Na/c11-10(12)8-4-7-9-5-2-1-3-6-9;/h1-3,5-6H,4,7-8H2,(H,11,12);/q;+1/p-1<sup> <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></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:VPZRWNZGLKXFOE-UHFFFAOYSA-M<sup> <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></div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-below"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style><span class="nobold"> <sup><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span><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> <a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">(what is this?)</a></span><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488"><span class="nobold">  <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=464403036&page2=Sodium+phenylbutyrate">(verify)</a></span></span></td></tr></tbody></table> <p><b>Sodium phenylbutyrate</b>, sold under the brand name <b>Buphenyl</b> among others, is a salt of an aromatic fatty acid, <a href="/wiki/4-phenylbutyrate" class="mw-redirect" title="4-phenylbutyrate">4-phenylbutyrate</a> (4-PBA) or 4-phenylbutyric acid.<sup id="cite_ref-r&d_7-0" class="reference"><a href="#cite_note-r&d-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> The compound is used to treat <a href="/wiki/Urea_cycle_disorder" class="mw-redirect" title="Urea cycle disorder">urea cycle disorders</a>, because its metabolites offer an alternative pathway to the urea cycle to allow excretion of excess nitrogen.<sup id="cite_ref-batshaw_8-0" class="reference"><a href="#cite_note-batshaw-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>Sodium phenylbutyrate is also a <a href="/wiki/Histone_deacetylase_inhibitor" title="Histone deacetylase inhibitor">histone deacetylase inhibitor</a> and <a href="/wiki/Chemical_chaperone" title="Chemical chaperone">chemical chaperone</a>, leading respectively to research into its use as an <a href="/wiki/Anti-cancer_agent" class="mw-redirect" title="Anti-cancer agent">anti-cancer agent</a> and in <a href="/wiki/Protein_misfolding" class="mw-redirect" title="Protein misfolding">protein misfolding</a> diseases such as <a href="/wiki/Cystic_fibrosis" title="Cystic fibrosis">cystic fibrosis</a>.<sup id="cite_ref-r&d_7-1" class="reference"><a href="#cite_note-r&d-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Structure_and_properties">Structure and properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_phenylbutyrate&action=edit&section=1" title="Edit section: Structure and properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Sodium phenylbutyrate is a sodium salt of an aromatic fatty acid, made up of an <a href="/wiki/Aromatic_ring" class="mw-redirect" title="Aromatic ring">aromatic ring</a> and <a href="/wiki/Butyric_acid" title="Butyric acid">butyric acid</a>. The chemical name for sodium phenylbutyrate is 4-phenylbutyric acid, sodium salt. It forms water-soluble off-white crystals.<sup id="cite_ref-Buphenyl_FDA_label_4-1" class="reference"><a href="#cite_note-Buphenyl_FDA_label-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_phenylbutyrate&action=edit&section=2" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Medical_uses">Medical uses</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_phenylbutyrate&action=edit&section=3" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Sodium phenylbutyrate is taken orally or by <a href="/wiki/Nasogastric_intubation" class="mw-redirect" title="Nasogastric intubation">nasogastric intubation</a> as a tablet or powder, and tastes very salty and bitter. It treats <a href="/wiki/Urea_cycle_disorder" class="mw-redirect" title="Urea cycle disorder">urea cycle disorders</a>, genetic diseases in which nitrogen waste builds up in the blood plasma as <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> glutamine (a state called <a href="/wiki/Hyperammonemia" title="Hyperammonemia">hyperammonemia</a>) due to deficiences in the <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> <a href="/wiki/Carbamoyl_phosphate_synthetase_I" title="Carbamoyl phosphate synthetase I">carbamoyl phosphate synthetase I</a>, <a href="/wiki/Ornithine_transcarbamylase" title="Ornithine transcarbamylase">ornithine transcarbamylase</a>, or <a href="/wiki/Argininosuccinic_acid_synthetase" class="mw-redirect" title="Argininosuccinic acid synthetase">argininosuccinic acid synthetase</a>.<sup id="cite_ref-batshaw_8-1" class="reference"><a href="#cite_note-batshaw-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Buphenyl_FDA_label_4-2" class="reference"><a href="#cite_note-Buphenyl_FDA_label-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Uncontrolled, this causes intellectual impairment and early death.<sup id="cite_ref-Buphenyl_FDA_label_4-3" class="reference"><a href="#cite_note-Buphenyl_FDA_label-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Sodium phenylbutyrate metabolites allows the kidneys to excrete excess nitrogen in place of <a href="/wiki/Urea" title="Urea">urea</a>, and coupled with dialysis, amino acid supplements and a protein-restricted diet, children born with urea cycle disorders can usually survive beyond 12 months.<sup id="cite_ref-Buphenyl_FDA_label_4-4" class="reference"><a href="#cite_note-Buphenyl_FDA_label-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Patients may need treatment for all their life.<sup id="cite_ref-Buphenyl_FDA_label_4-5" class="reference"><a href="#cite_note-Buphenyl_FDA_label-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> The treatment was introduced by researchers in the 1990s, and approved by the U.S. <a href="/wiki/Food_and_Drugs_Administration" class="mw-redirect" title="Food and Drugs Administration">Food and Drugs Administration</a> (FDA) in April 1996.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Adverse_effects">Adverse effects</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_phenylbutyrate&action=edit&section=4" title="Edit section: Adverse effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Nearly <style data-mw-deduplicate="TemplateStyles:r1154941027">.mw-parser-output .frac{white-space:nowrap}.mw-parser-output .frac .num,.mw-parser-output .frac .den{font-size:80%;line-height:0;vertical-align:super}.mw-parser-output .frac .den{vertical-align:sub}.mw-parser-output .sr-only{border:0;clip:rect(0,0,0,0);clip-path:polygon(0px 0px,0px 0px,0px 0px);height:1px;margin:-1px;overflow:hidden;padding:0;position:absolute;width:1px}</style><span class="frac"><span class="num">1</span>⁄<span class="den">4</span></span> of women may experience an <a href="/wiki/Adverse_effect" title="Adverse effect">adverse effect</a> of <a href="/wiki/Amenorrhea" title="Amenorrhea">amenorrhea</a> or menstrual dysfunction.<sup id="cite_ref-Buphenyl_FDA_label_4-6" class="reference"><a href="#cite_note-Buphenyl_FDA_label-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Appetite loss is seen in 4% of patients. Body odor due to metabolization of phenylbutyrate affects 3% of patients, and 3% experience unpleasant tastes. Gastrointestinal symptoms and mostly mild indications of <a href="/wiki/Neurotoxicity" title="Neurotoxicity">neurotoxicity</a> are also seen in less than 2% of patients, among several other reported adverse effects.<sup id="cite_ref-Buphenyl_FDA_label_4-7" class="reference"><a href="#cite_note-Buphenyl_FDA_label-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Administration during pregnancy is not recommended because sodium phenylbutyrate treatment could mimic maternal <a href="/wiki/Phenylketonuria" title="Phenylketonuria">phenylketonuria</a> due to the production of phenylalanine, potentially causing fetal brain damage.<sup id="cite_ref-batshaw_8-2" class="reference"><a href="#cite_note-batshaw-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Research">Research</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_phenylbutyrate&action=edit&section=5" title="Edit section: Research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Urea_cycle_disorders">Urea cycle disorders</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_phenylbutyrate&action=edit&section=6" title="Edit section: Urea cycle disorders"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Sodium phenylbutyrate administration was discovered to lead to an alternative nitrogen disposal pathway by Dr. <a href="/w/index.php?title=Saul_Brusilow&action=edit&redlink=1" class="new" title="Saul Brusilow (page does not exist)">Saul Brusilow</a>, <a href="/wiki/Mark_Batshaw" title="Mark Batshaw">Mark Batshaw</a> and colleagues at the <a href="/wiki/Johns_Hopkins_School_of_Medicine" title="Johns Hopkins School of Medicine">Johns Hopkins School of Medicine</a> in the early 1980s, due to some serendipitous discoveries. They had studied <a href="/wiki/Ketoacid" class="mw-redirect" title="Ketoacid">ketoacid</a> therapy for another <a href="/wiki/Inborn_error_of_metabolism" class="mw-redirect" title="Inborn error of metabolism">inborn error of metabolism</a>, <a href="/wiki/Citrullinemia" title="Citrullinemia">citrullinemia</a>, in the late 1970s and they noticed that <a href="/wiki/Arginine" title="Arginine">arginine</a> treatment led to an increase of nitrogen in the urine and a drop in ammonia in the blood. The researchers spoke to <a href="/wiki/Norman_Radin" title="Norman Radin">Norman Radin</a> about this finding, and he remembered a 1914 article on using <a href="/wiki/Sodium_benzoate" title="Sodium benzoate">sodium benzoate</a> to reduce urea excretion. Another 1919 article had used sodium phenylacetate, and so the researchers treated five patients with hyperammonemia with benzoate and phenylacetate and published a report in <i><a href="/wiki/Science_(journal)" title="Science (journal)">Science</a></i>.<sup id="cite_ref-batshaw_8-3" class="reference"><a href="#cite_note-batshaw-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> In 1982 and 1984, the researchers published on using benzoate and arginine for urea cycle disorders in the <i><a href="/wiki/NEJM" class="mw-redirect" title="NEJM">NEJM</a></i>.<sup id="cite_ref-batshaw_8-4" class="reference"><a href="#cite_note-batshaw-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Use of sodium phenylbutyrate was introduced in the early 1990s, as it lacks the odor of phenylacetate.<sup id="cite_ref-batshaw_8-5" class="reference"><a href="#cite_note-batshaw-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Chemical_chaperone">Chemical chaperone</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_phenylbutyrate&action=edit&section=7" title="Edit section: Chemical chaperone"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In <a href="/wiki/Cystic_fibrosis" title="Cystic fibrosis">cystic fibrosis</a>, a point mutation in the <a href="/wiki/Cystic_Fibrosis_Transmembrane_Conductance_Regulator" class="mw-redirect" title="Cystic Fibrosis Transmembrane Conductance Regulator">Cystic Fibrosis Transmembrane Conductance Regulator</a> protein, ΔF508-CFTR, causes it to be unstable and misfold, hence trapped in the endoplasmic reticulum and unable to reach the cell membrane. This lack of CFTR in the cell membrane leads to disrupted chloride transport and the symptoms of cystic fibrosis. Sodium phenylbutyrate can act as a <a href="/wiki/Chemical_chaperone" title="Chemical chaperone">chemical chaperone</a>, stabilising the mutant CFTR in the endoplasmic reticulum and allowing it to reach the cell surface.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Histone_deacetylase_inhibitor">Histone deacetylase inhibitor</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_phenylbutyrate&action=edit&section=8" title="Edit section: Histone deacetylase inhibitor"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Deriving from its activity as a <a href="/wiki/Histone_deacetylase_inhibitor" title="Histone deacetylase inhibitor">histone deacetylase inhibitor</a>, sodium phenylbutyrate is under investigation for use as a potential differentiation-inducing agent in malignant <a href="/wiki/Glioma" title="Glioma">glioma</a> and <a href="/wiki/Acute_myeloid_leukaemia" class="mw-redirect" title="Acute myeloid leukaemia">acute myeloid leukaemia</a>,<sup id="cite_ref-r&d_7-2" class="reference"><a href="#cite_note-r&d-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> and also for the treatment of some <a href="/wiki/Sickle-cell" class="mw-redirect" title="Sickle-cell">sickle-cell</a> disorders as an alternative to <a href="/wiki/Hydroxycarbamide" title="Hydroxycarbamide">hydroxycarbamide</a> due to it inducing expression of <a href="/wiki/Fetal_hemoglobin" title="Fetal hemoglobin">fetal hemoglobin</a> to replace missing adult hemoglobin.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> While small-scale investigation is proceeding, there is to date no published data to support the use of the compound in the clinical treatment of cancer, and it remains under limited investigation. Sodium phenylbutyrate is also being studied as a therapeutic option for the treatment of Huntington's disease.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Other">Other</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_phenylbutyrate&action=edit&section=9" title="Edit section: Other"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Phenylbutyrate has been associated with longer lifespans in <i><a href="/wiki/Drosophila" title="Drosophila">Drosophila</a></i>.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p><p>University of Colorado researchers Curt Freed and Wenbo Zhou demonstrated that phenylbutyrate stops the progression of <a href="/wiki/Parkinson%27s_disease" title="Parkinson's disease">Parkinson's disease</a> in mice by turning on a gene called <a href="/wiki/DJ-1" title="DJ-1">DJ-1</a> that can protect <a href="/wiki/Dopaminergic" title="Dopaminergic">dopaminergic</a> neurons in the <a href="/wiki/Midbrain" title="Midbrain">midbrain</a> from dying. As of July 2011<sup class="plainlinks noexcerpt noprint asof-tag update" style="display:none;"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Sodium_phenylbutyrate&action=edit">[update]</a></sup> they plan on testing phenylbutyrate for the treatment of Parkinson's disease in humans.<sup id="cite_ref-pmid21902286_22-0" class="reference"><a href="#cite_note-pmid21902286-22"><span class="cite-bracket">[</span>22<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=Sodium_phenylbutyrate&action=edit&section=10" title="Edit section: Pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Nitrogen_elimination.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fd/Nitrogen_elimination.jpg/450px-Nitrogen_elimination.jpg" decoding="async" width="450" height="217" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/f/fd/Nitrogen_elimination.jpg 1.5x" data-file-width="642" data-file-height="309" /></a><figcaption>Nitrogen elimination by phenylbutyrate metabolites</figcaption></figure> <p>Phenylbutyrate is a <a href="/wiki/Prodrug" title="Prodrug">prodrug</a>. In the human body it is first converted to phenylbutyryl-CoA and then <a href="/wiki/Metabolized" class="mw-redirect" title="Metabolized">metabolized</a> by mitochondrial <a href="/wiki/Beta-oxidation" class="mw-redirect" title="Beta-oxidation">beta-oxidation</a>, mainly in the liver and kidneys, to the active form, <a href="/wiki/Phenylacetic_acid" title="Phenylacetic acid">phenylacetate</a>.<sup id="cite_ref-:0_23-0" class="reference"><a href="#cite_note-:0-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> Phenylacetate conjugates with glutamine to <a href="/wiki/Phenylacetylglutamine" title="Phenylacetylglutamine">phenylacetylglutamine</a>, which is eliminated with the urine. It contains the same amount of nitrogen as urea, which makes it an alternative to urea for excreting nitrogen.<sup id="cite_ref-Buphenyl_FDA_label_4-8" class="reference"><a href="#cite_note-Buphenyl_FDA_label-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>Sodium phenylbutyrate taken by mouth can be detected in the blood within fifteen minutes, and reaches peak concentration in the bloodstream within an hour. It is metabolized into phenylacetate within half an hour.<sup id="cite_ref-Buphenyl_FDA_label_4-9" class="reference"><a href="#cite_note-Buphenyl_FDA_label-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div style="clear:both;" class=""></div> <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=Sodium_phenylbutyrate&action=edit&section=11" 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"> <div class="mw-references-wrap mw-references-columns"><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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.tga.gov.au/resources/publication/publications/prescription-medicines-registration-new-chemical-entities-australia-2017">"Prescription medicines: registration of new chemical entities in Australia, 2017"</a>. <i>Therapeutic Goods Administration (TGA)</i>. 21 June 2022<span class="reference-accessdate">. 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These findings lead the author to conclude that phenylbutyrate suppresses ER stress by directly reducing the amount of misfolded protein, including Pael-R accumulated in the ER.[175]</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Drugs+in+R%26D&rft.atitle=Clinical+and+experimental+applications+of+sodium+phenylbutyrate&rft.volume=11&rft.issue=3&rft.pages=227-249&rft.date=2011-09&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3586072%23id-name%3DPMC&rft_id=info%3Apmid%2F21902286&rft_id=info%3Adoi%2F10.2165%2F11591280-000000000-00000&rft.aulast=Iannitti&rft.aufirst=T&rft.au=Palmieri%2C+B&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3586072&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASodium+phenylbutyrate" class="Z3988"></span></span> </li> <li id="cite_note-:0-23"><span class="mw-cite-backlink"><b><a href="#cite_ref-:0_23-0">^</a></b></span> <span class="reference-text"><link 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class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23141465">23141465</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Molecular+Genetics+and+Metabolism&rft.atitle=Evidence+for+involvement+of+medium+chain+acyl-CoA+dehydrogenase+in+the+metabolism+of+phenylbutyrate&rft.volume=107&rft.issue=4&rft.pages=684-689&rft.date=2012-12&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3504130%23id-name%3DPMC&rft_id=info%3Apmid%2F23141465&rft_id=info%3Adoi%2F10.1016%2Fj.ymgme.2012.10.009&rft.aulast=Kormanik&rft.aufirst=K&rft.au=Kang%2C+H&rft.au=Cuebas%2C+D&rft.au=Vockley%2C+J&rft.au=Mohsen%2C+AW&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3504130&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASodium+phenylbutyrate" class="Z3988"></span></span> </li> </ol></div></div> <div class="navbox-styles"><style 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id="Other_alimentary_tract_and_metabolism_products_(A16)" style="font-size:114%;margin:0 4em">Other <a href="/wiki/Alimentary_tract" class="mw-redirect" title="Alimentary tract">alimentary tract</a> and <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> products (<a href="/wiki/ATC_code_A16" title="ATC code A16">A16</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Amino_acid" title="Amino acid">Amino acids</a> and derivatives</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/S-Adenosyl_methionine" title="S-Adenosyl methionine">Ademetionine</a></li> <li><a href="/wiki/Betaine" title="Betaine">Betaine</a></li> <li><a href="/wiki/Carglumic_acid" title="Carglumic acid">Carglumic acid</a></li> <li><a href="/wiki/Glutamine" title="Glutamine">Glutamine</a></li> <li><a href="/wiki/Levocarnitine" class="mw-redirect" title="Levocarnitine">Levocarnitine</a></li> <li><a href="/wiki/Mercaptamine" class="mw-redirect" title="Mercaptamine">Mercaptamine</a></li> <li><a href="/wiki/Metreleptin" title="Metreleptin">Metreleptin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Enzyme" title="Enzyme">Enzymes</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/Amino_acid" title="Amino acid">Amino acids</a>: <i><a href="/wiki/Phenylalanine_ammonia-lyase" title="Phenylalanine ammonia-lyase">phenylalanine ammonia-lyase</a></i> (<a href="/wiki/Pegvaliase" title="Pegvaliase">Pegvaliase</a>)</li></ul> <ul><li><a href="/wiki/Carbohydrate_metabolism" title="Carbohydrate metabolism">Carbohydrate metabolism</a>: <i><a href="/wiki/Sucrase" title="Sucrase">sucrase</a></i> (<a href="/wiki/Sacrosidase" title="Sacrosidase">Sacrosidase</a>)</li> <li><i><a href="/wiki/Alpha-glucosidase" class="mw-redirect" title="Alpha-glucosidase">alpha-glucosidase</a></i> (<a href="/wiki/Alglucosidase_alfa" title="Alglucosidase alfa">Alglucosidase alfa</a>, <a href="/wiki/Avalglucosidase_alfa" title="Avalglucosidase alfa">Avalglucosidase alfa</a>, <a href="/wiki/Cipaglucosidase_alfa" title="Cipaglucosidase alfa">Cipaglucosidase alfa</a>)</li></ul> <ul><li><a href="/wiki/Glycolipid" title="Glycolipid">Glycolipid</a>/<a href="/wiki/Sphingolipid" title="Sphingolipid">sphingolipid</a>: <i><a href="/wiki/Glucocerebrosidase" title="Glucocerebrosidase">glucocerebrosidase</a></i> (<a href="/wiki/Alglucerase" title="Alglucerase">Alglucerase</a></li> <li><a href="/wiki/Imiglucerase" title="Imiglucerase">Imiglucerase</a></li> <li><a href="/wiki/Taliglucerase_alfa" title="Taliglucerase alfa">Taliglucerase alfa</a></li> <li><a href="/wiki/Velaglucerase_alfa" title="Velaglucerase alfa">Velaglucerase alfa</a>)</li> <li><i><a href="/wiki/Alpha-galactosidase" class="mw-redirect" title="Alpha-galactosidase">alpha-galactosidase</a></i> (<a href="/wiki/Agalsidase_alfa" class="mw-redirect" title="Agalsidase alfa">Agalsidase alfa</a></li> <li><a href="/wiki/Agalsidase_beta" class="mw-redirect" title="Agalsidase beta">Agalsidase beta</a></li> <li><a href="/wiki/Pegunigalsidase_alfa" title="Pegunigalsidase alfa">Pegunigalsidase alfa</a>)</li></ul> <ul><li><a href="/wiki/Glycosaminoglycan" title="Glycosaminoglycan">Glycosaminoglycan</a>: <i><a href="/wiki/Iduronidase" title="Iduronidase">iduronidase</a></i> (<a href="/wiki/Laronidase" class="mw-redirect" title="Laronidase">Laronidase</a>)</li> <li><i><a href="/wiki/Arylsulfatase_B" title="Arylsulfatase B">arylsulfatase B</a></i> (<a href="/wiki/Galsulfase" class="mw-redirect" title="Galsulfase">Galsulfase</a>)</li> <li><i><a href="/wiki/Iduronate-2-sulfatase" title="Iduronate-2-sulfatase">iduronate-2-sulfatase</a></i> (<a href="/wiki/Idursulfase" title="Idursulfase">Idursulfase</a>)</li> <li><a href="/w/index.php?title=Idursulfase_beta&action=edit&redlink=1" class="new" title="Idursulfase beta (page does not exist)">idursulfase beta</a></li></ul> <ul><li><a href="/wiki/Lipid" title="Lipid">Lipid</a>: <i><a href="/wiki/Lysosomal_lipase" title="Lysosomal lipase">lysosomal lipase</a></i> (<a href="/wiki/Sebelipase_alfa" title="Sebelipase alfa">Sebelipase alfa</a>)</li></ul> <ul><li><a href="/wiki/Phosphate" title="Phosphate">Phosphate</a>: <a href="/wiki/Asfotase_alfa" title="Asfotase alfa">Asfotase alfa</a></li></ul> <ul><li><a href="/wiki/Atidarsagene_autotemcel" title="Atidarsagene autotemcel">atidarsagene autotemcel</a></li> <li><a href="/wiki/Cerliponase_alfa" title="Cerliponase alfa">cerliponase alfa</a></li> <li><a href="/wiki/Eladocagene_exuparvovec" title="Eladocagene exuparvovec">eladocagene exuparvovec</a></li> <li><a href="/wiki/Elosulfase_alfa" title="Elosulfase alfa">elosulfase alfa</a></li> <li><a href="/wiki/Olipudase_alfa" title="Olipudase alfa">olipudase alfa</a></li> <li><a href="/w/index.php?title=Pabinafusp_alfa&action=edit&redlink=1" class="new" title="Pabinafusp alfa (page does not exist)">pabinafusp alfa</a></li> <li><a href="/wiki/Pegzilarginase" title="Pegzilarginase">pegzilarginase</a></li> <li><a href="/wiki/Vestronidase_alfa" title="Vestronidase alfa">vestronidase alfa</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-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Anethole_trithione" title="Anethole trithione">Anethole trithione</a></li> <li><a href="/wiki/Eliglustat" title="Eliglustat">Eliglustat</a></li> <li><a href="/wiki/Givosiran" title="Givosiran">Givosiran</a></li> <li><a href="/wiki/Glycerol_phenylbutyrate" title="Glycerol phenylbutyrate">Glycerol phenylbutyrate</a></li> <li><a href="/wiki/Leriglitazone" title="Leriglitazone">Leriglitazone</a></li> <li><a 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href="/wiki/Diallyl_disulfide" title="Diallyl disulfide">Diallyl disulfide</a></li> <li><a href="/wiki/Entinostat" title="Entinostat">Entinostat</a></li> <li><a href="/w/index.php?title=Fimepinostat&action=edit&redlink=1" class="new" title="Fimepinostat (page does not exist)">Fimepinostat</a></li> <li><a href="/wiki/Givinostat" title="Givinostat">Givinostat</a></li> <li><a href="/wiki/Indole-3-carbinol" title="Indole-3-carbinol">Indole-3-carbinol</a></li> <li><a href="/w/index.php?title=Kevetrin&action=edit&redlink=1" class="new" title="Kevetrin (page does not exist)">Kevetrin</a></li> <li><a href="/wiki/Martinostat" title="Martinostat">Martinostat</a></li> <li><a href="/wiki/Mocetinostat" title="Mocetinostat">Mocetinostat</a></li> <li><a href="/wiki/Niacinamide" class="mw-redirect" title="Niacinamide">Niacinamide</a></li> <li><a href="/wiki/Panobinostat" title="Panobinostat">Panobinostat</a></li> <li><a href="/wiki/Parthenolide" title="Parthenolide">Parthenolide</a></li> <li><a href="/wiki/Phenylbutyrate" class="mw-redirect" title="Phenylbutyrate">Phenylbutyrate</a></li> <li><a href="/wiki/Pracinostat" title="Pracinostat">Pracinostat</a></li> <li><a href="/wiki/Quisinostat" title="Quisinostat">Quisinostat</a></li> <li><a href="/wiki/Resminostat" title="Resminostat">Resminostat</a></li> <li><a href="/wiki/Romidepsin" title="Romidepsin">Romidepsin</a></li> <li><a href="/wiki/Scriptaid" title="Scriptaid">Scriptaid</a></li> <li><a href="/wiki/Sodium_butyrate" title="Sodium butyrate">Sodium butyrate</a></li> <li><a href="/wiki/Sodium_oxybate" title="Sodium oxybate">Sodium oxybate (GHB sodium)</a></li> <li><a class="mw-selflink selflink">Sodium phenylbutyrate</a></li> <li><a href="/wiki/Sodium_valproate" class="mw-redirect" title="Sodium valproate">Sodium valproate</a></li> <li><a href="/wiki/Sulforaphane" title="Sulforaphane">Sulforaphane</a></li> <li><a href="/w/index.php?title=Trapoxin_B&action=edit&redlink=1" class="new" title="Trapoxin B (page does not exist)">Trapoxin B</a></li> <li><a href="/wiki/Trichostatin_A" title="Trichostatin A">Trichostatin A</a></li> <li><a href="/wiki/Tucidinostat" title="Tucidinostat">Tucidinostat</a></li> <li><a href="/wiki/Valnoctamide" title="Valnoctamide">Valnoctamide</a></li> <li><a href="/wiki/Valproate" title="Valproate">Valproic acid (valproate)</a></li> <li><a href="/wiki/Valproate_pivoxil" title="Valproate pivoxil">Valproate pivoxil</a></li> <li><a href="/wiki/Valproate_semisodium" class="mw-redirect" title="Valproate semisodium">Valproate semisodium</a></li> <li><a href="/wiki/Valpromide" title="Valpromide">Valpromide</a></li> <li><a href="/wiki/Vorinostat" title="Vorinostat">Vorinostat (SAHA)</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></div></td></tr></tbody></table></div> <style 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