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Available in 10 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-10" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">10 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%AC%DB%8C%DB%B4%DB%B1%DB%B8" title="جی۴۱۸ – South Azerbaijani" lang="azb" hreflang="azb" data-title="جی۴۱۸" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Geneticin" title="Geneticin – German" lang="de" hreflang="de" data-title="Geneticin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%AC%DB%8C%DB%B4%DB%B1%DB%B8" title="جی۴۱۸ – Persian" lang="fa" hreflang="fa" data-title="جی۴۱۸" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/G%C3%A9n%C3%A9ticine" title="Généticine – French" lang="fr" hreflang="fr" data-title="Généticine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Geneticina" title="Geneticina – Italian" lang="it" hreflang="it" data-title="Geneticina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/G418" title="G418 – Japanese" lang="ja" hreflang="ja" data-title="G418" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/G418" title="G418 – Serbian" lang="sr" hreflang="sr" data-title="G418" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/G418" title="G418 – Serbo-Croatian" lang="sh" hreflang="sh" data-title="G418" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%88%E0%B8%B5%E0%B8%99%E0%B8%B5%E0%B8%95%E0%B8%B4%E0%B8%8B%E0%B8%B4%E0%B8%99" title="จีนีติซิน – Thai" lang="th" hreflang="th" data-title="จีนีติซิน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/G418" title="G418 – Chinese" lang="zh" hreflang="zh" data-title="G418" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a 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figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> <table class="infobox ib-chembox"> <caption>G418 </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:G418.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/03/G418.svg/160px-G418.svg.png" decoding="async" width="160" height="210" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/03/G418.svg/240px-G418.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/03/G418.svg/320px-G418.svg.png 2x" data-file-width="158" data-file-height="207" /></a><figcaption></figcaption></figure> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">(1<i>S</i>,2<i>S</i>,3<i>R</i>,4<i>S</i>,6<i>R</i>)-4,6-Diamino-2-hydroxycyclohexane-1,3-diyl 1-(3-amino-3-deoxy-4-<i>C</i>-methyl-β-<small>L</small>-arabinopyranoside) 3-(2-amino-2,7-dideoxy-<small>D</small>-<i>glycero</i>-α-<small>D</small>-<i>gluco</i>-heptopyranoside)</div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">(2<i>R</i>,3<i>S</i>,4<i>R</i>,5<i>R</i>,6<i>S</i>)-5-Amino-6-{[(1<i>R</i>,2<i>S</i>,3<i>S</i>,4<i>R</i>,6<i>S</i>)-4,6-diamino-3-{[(2<i>R</i>,3<i>R</i>,4<i>R</i>,5<i>R</i>)-3,5-dihydroxy-5-methyl-4-(methylamino)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-2-[(1<i>R</i>)-1-hydroxyethyl]oxane-3,4-diol</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Geneticin<br /><i>O</i>-2-Amino-2,7-didesoxy-<small>D</small>-glycero-α-<small>D</small>-gluco-heptopyranosyl-(1→4)-<i>O</i>-(3-desoxy-4-<i>C</i>-methyl-3-(methylamino)-β-<small>L</small>-arabinopyranosyl- (1→6))-<small>D</small>-streptamin</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><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=49863-47-0">49863-47-0</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><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=108321-42-2">108321-42-2</a></span> (disulfate salt)<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> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><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=O%5BC%40H%5D3%5BC%40H%5D%28O%29%5BC%40%40H%5D%28N%29%5BC%40%40H%5D%28O%5BC%40%40H%5D2%5BC%40%40H%5D%28N%29C%5BC%40%40H%5D%28N%29%5BC%40H%5D%28O%5BC%40H%5D1OC%5BC%40%5D%28C%29%28O%29%5BC%40H%5D%28NC%29%5BC%40H%5D1O%29%5BC%40H%5D2O%29OC3%5BC%40%40H%5D%28O%29C">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><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/ChEMBL215226">ChEMBL215226</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> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><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.21106441.html">21106441</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> <td><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a> </td> <td><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/DB04263">DB04263</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> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><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/123865">123865</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><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/A08F5XTI6G">A08F5XTI6G</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> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><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></div> </td> <td><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/DTXSID10198129">DTXSID10198129</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q410036#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> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><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="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C20H40N4O10/c1-6(25)14-11(27)10(26)9(23)18(32-14)33-15-7(21)4-8(22)16(12(15)28)34-19-13(29)17(24-3)20(2,30)5-31-19/h6-19,24-30H,4-5,21-23H2,1-3H3/t6-,7-,8+,9+,10+,11-,12-,13+,14?,15+,16-,17+,18+,19+,20-/m0/s1<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><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: BRZYSWJRSDMWLG-NQRKCNNJSA-N<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></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C20H40N4O10/c1-6(25)14-11(27)10(26)9(23)18(32-14)33-15-7(21)4-8(22)16(12(15)28)34-19-13(29)17(24-3)20(2,30)5-31-19/h6-19,24-30H,4-5,21-23H2,1-3H3/t6-,7-,8+,9+,10+,11-,12-,13+,14?,15+,16-,17+,18+,19+,20-/m0/s1</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: BRZYSWJRSDMWLG-NQRKCNNJBI</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><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="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">O[C@H]3[C@H](O)[C@@H](N)[C@@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]1OC[C@](C)(O)[C@H](NC)[C@H]1O)[C@H]2O)OC3[C@@H](O)C</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>20</sub><span title="Hydrogen">H</span><sub>40</sub><span title="Nitrogen">N</span><sub>4</sub><span title="Oxygen">O</span><sub>10</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002496558000000000♠"></span>496.558</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>50 mg/mL </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=461115152&page2=G418">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <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><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> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>G418</b> (<b>geneticin</b>) is an <a href="/wiki/Aminoglycoside" title="Aminoglycoside">aminoglycoside</a> <a href="/wiki/Antibiotic" title="Antibiotic">antibiotic</a> similar in structure to <a href="/wiki/Gentamicin_B1" class="mw-redirect" title="Gentamicin B1">gentamicin B1</a>. It is produced by <i><a href="/wiki/Micromonospora_rhodorangea" class="mw-redirect" title="Micromonospora rhodorangea">Micromonospora rhodorangea</a></i>.<sup id="cite_ref-In_1-0" class="reference"><a href="#cite_note-In-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> G418 blocks <a href="/wiki/Polypeptide_synthesis" class="mw-redirect" title="Polypeptide synthesis">polypeptide synthesis</a> by inhibiting the elongation step in both <a href="/wiki/Prokaryotic" class="mw-redirect" title="Prokaryotic">prokaryotic</a> and <a href="/wiki/Eukaryotic" class="mw-redirect" title="Eukaryotic">eukaryotic</a> cells.<sup id="cite_ref-In_1-1" class="reference"><a href="#cite_note-In-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Resistance to G418 is conferred by the neo gene from Tn5 encoding an aminoglycoside 3'-phosphotransferase, APT 3' II.<sup id="cite_ref-In_1-2" class="reference"><a href="#cite_note-In-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> G418 is an analog of <a href="/wiki/Neomycin" title="Neomycin">neomycin</a> sulfate, and has similar mechanism as <a href="/wiki/Neomycin" title="Neomycin">neomycin</a>. G418 is commonly used in laboratory research to select genetically engineered cells .<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> In general, for bacteria and algae, concentrations of 5 μg/mL or less are used; for mammalian cells, concentrations of approximately 400 μg/mL are used for selection and 200 μg/mL for maintenance. However, optimal concentration for resistant clones selection in mammalian cells depends on the <a href="/wiki/Cell_line" class="mw-redirect" title="Cell line">cell line</a> used as well as on the <a href="/wiki/Plasmid" title="Plasmid">plasmid</a> carrying the resistance gene. Therefore, antibiotic titration should be done to find the best condition for every experimental system. Titration should be done using antibiotic concentrations ranging from 100 μg/mL up to 1400 μg/mL. Resistant clones selection could require from 1 to up to 3 weeks.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (March 2023)">citation needed</span></a></i>]</sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="G418_impurity_profile">G418 impurity profile</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=G418&action=edit&section=1" title="Edit section: G418 impurity profile"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>G418 is produced by <a href="/wiki/Fermentation" title="Fermentation">fermentation</a> and isolation processes and the G418 producing strain <i><a href="/wiki/Micromonospora_rhodorangea" class="mw-redirect" title="Micromonospora rhodorangea">Micromonospora rhodorangea</a></i> produces many other gentamicins while producing G418. The common impurities of G418 include gentamicins A, C1, C1a, C2, C2a and X2.<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> The quality of G418 is not based on just the potency, but more on the selectivity defined by the killing curve of the sensitive cells vs the resistant cells. A good G418 product has the lowest <a href="/wiki/Median_lethal_dose" title="Median lethal dose">LD<sub style="font-size:-1">50</sub></a> for sensitive cells (such as NIH <a href="/wiki/3T3_cells" title="3T3 cells">3T3</a>) and the highest LD<sub>50</sub> (can be up to 5,000 μg/ml) for resistant cells (NIH <a href="/wiki/3T3_cells" title="3T3 cells">3T3</a> transfected with resistant genes). Gentamicins have almost no selectivity, except gentamicin X2.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Use_in_cell_biology">Use in cell biology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=G418&action=edit&section=2" title="Edit section: Use in cell biology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>G418 is routinely used as a selective agent in cell culture set-ups. Researchers can link the <i>neoR</i> selective resistance gene with their vector. Then if the vector is successfully introduced into cells, the cells can become G418-resistant cells. After treating with G418, these vector(-) cells will die, while vector(+) cells will survive. This method can help researchers select vector(+) cells.<sup id="cite_ref-In_1-3" class="reference"><a href="#cite_note-In-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Lodish2013_5-0" class="reference"><a href="#cite_note-Lodish2013-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Mechanism_of_action">Mechanism of action</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=G418&action=edit&section=3" title="Edit section: Mechanism of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>G418 Disulfate and other aminoglycosides prevent protein synthesis at the early stages of elongation, post-initiation, initiation of translation. Resistance to G418 Disulfate is conferred by the Neomycin resistance gene (<i>neo)</i> from either Tn5 or Tn601 (903) transposons. Cells transfected with resistance plasmids containing the <i>neo</i> gene can express aminoglycoside 3'-phosphotransferase (APT 3' I or APT 3' II) which covalently modifies G418 to 3-phosphoric G418,  which has negligible potency and has low-affinity for prokaryotic and eukaryotic ribosomes.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<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=G418&action=edit&section=4" 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"><ol class="references"> <li id="cite_note-In-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-In_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-In_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-In_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-In_1-3"><sup><i><b>d</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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.thermofisher.com/us/en/home/life-science/cell-culture/transfection/selection/g418.html">"Geneticin"</a>. <i>Thermo Fisher Scientific</i>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170808034522/https://www.thermofisher.com/us/en/home/life-science/cell-culture/transfection/selection/g418.html">Archived</a> from the original on 2017-08-08<span class="reference-accessdate">. Retrieved <span class="nowrap">2017-08-07</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Thermo+Fisher+Scientific&rft.atitle=Geneticin&rft_id=https%3A%2F%2Fwww.thermofisher.com%2Fus%2Fen%2Fhome%2Flife-science%2Fcell-culture%2Ftransfection%2Fselection%2Fg418.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AG418" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20091229191551/http://www.exactantigen.com/review/G418.html">"G418"</a>. <i>labome.com</i>. Archived from <a rel="nofollow" class="external text" href="http://www.exactantigen.com/review/G418.html">the original</a> on 2009-12-29<span class="reference-accessdate">. Retrieved <span class="nowrap">2010-01-09</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=labome.com&rft.atitle=G418&rft_id=http%3A%2F%2Fwww.exactantigen.com%2Freview%2FG418.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AG418" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20160303233452/http://www.g418-evopure.com/structures.html">"G418 impurity profile"</a>. Archived from <a rel="nofollow" class="external text" href="http://www.g418-evopure.com/structures.html">the original</a> on 2016-03-03<span class="reference-accessdate">. Retrieved <span class="nowrap">2011-10-03</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=G418+impurity+profile&rft_id=http%3A%2F%2Fwww.g418-evopure.com%2Fstructures.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AG418" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20160205024043/http://g418-evopure.com/Technical.html">"G418 selectivity"</a>. Archived from <a rel="nofollow" class="external text" href="http://www.g418-evopure.com/Technical.html">the original</a> on 2016-02-05<span class="reference-accessdate">. Retrieved <span class="nowrap">2011-07-14</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=G418+selectivity&rft_id=http%3A%2F%2Fwww.g418-evopure.com%2FTechnical.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AG418" class="Z3988"></span></span> </li> <li id="cite_note-Lodish2013-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-Lodish2013_5-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHarvey_Lodish2013" class="citation book cs1">Harvey Lodish; et al. (2013). "Chapter5: Molecular Genetic Techniques". <i>Molecular Cell Biology</i> (7th ed.). Macmillan Higher Education. pp. <span class="nowrap">171–</span>223. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4641-0981-2" title="Special:BookSources/978-1-4641-0981-2"><bdi>978-1-4641-0981-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Chapter5%3A+Molecular+Genetic+Techniques&rft.btitle=Molecular+Cell+Biology&rft.pages=%3Cspan+class%3D%22nowrap%22%3E171-%3C%2Fspan%3E223&rft.edition=7th&rft.pub=Macmillan+Higher+Education&rft.date=2013&rft.isbn=978-1-4641-0981-2&rft.au=Harvey+Lodish&rfr_id=info%3Asid%2Fen.wikipedia.org%3AG418" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://toku-e.com/g418-disulfate/">"G418 Disulfate"</a>. <i>TOKU-E</i><span class="reference-accessdate">. Retrieved <span class="nowrap">2024-06-28</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=TOKU-E&rft.atitle=G418+Disulfate&rft_id=https%3A%2F%2Ftoku-e.com%2Fg418-disulfate%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AG418" class="Z3988"></span></span> </li> </ol></div></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" 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=G418&oldid=1263298218">https://en.wikipedia.org/w/index.php?title=G418&oldid=1263298218</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:Aminoglycoside_antibiotics" title="Category:Aminoglycoside antibiotics">Aminoglycoside antibiotics</a></li><li><a href="/wiki/Category:Cell_culture_reagents" title="Category:Cell culture reagents">Cell culture reagents</a></li><li><a href="/wiki/Category:Eukaryotic_selection_compounds" title="Category:Eukaryotic selection compounds">Eukaryotic selection compounds</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:Chemical_articles_with_multiple_compound_IDs" title="Category:Chemical articles with multiple compound IDs">Chemical articles with multiple compound IDs</a></li><li><a href="/wiki/Category:Multiple_chemicals_in_an_infobox_that_need_indexing" title="Category:Multiple chemicals in an infobox that need indexing">Multiple chemicals in an infobox that need indexing</a></li><li><a href="/wiki/Category:Chemical_articles_with_multiple_CAS_registry_numbers" title="Category:Chemical articles with multiple CAS registry numbers">Chemical articles with multiple CAS registry numbers</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_with_changed_CASNo_identifier" title="Category:Articles with changed CASNo identifier">Articles with changed CASNo identifier</a></li><li><a href="/wiki/Category:Articles_with_changed_EBI_identifier" title="Category:Articles with changed EBI identifier">Articles with changed EBI identifier</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><li><a href="/wiki/Category:Chembox_image_size_set" title="Category:Chembox image size set">Chembox image size set</a></li><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:All_articles_with_unsourced_statements" title="Category:All articles with unsourced statements">All articles with unsourced statements</a></li><li><a href="/wiki/Category:Articles_with_unsourced_statements_from_March_2023" title="Category:Articles with unsourced statements from March 2023">Articles with unsourced statements from March 2023</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 15 December 2024, at 21:31<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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