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subsection</span> </button> <ul id="toc-Structure-activity_relationship-sublist" class="vector-toc-list"> <li id="toc-A-_and_B-ring_modification" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#A-_and_B-ring_modification"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>A- and B-ring modification</span> </div> </a> <ul id="toc-A-_and_B-ring_modification-sublist" class="vector-toc-list"> <li id="toc-Alkyl_substitution" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Alkyl_substitution"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1.1</span> <span>Alkyl substitution</span> </div> </a> <ul id="toc-Alkyl_substitution-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Hexacyclic_CPT_analogues" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Hexacyclic_CPT_analogues"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1.2</span> <span>Hexacyclic CPT analogues</span> </div> </a> <ul id="toc-Hexacyclic_CPT_analogues-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-C-_and_D-ring_modification" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#C-_and_D-ring_modification"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>C- and D-ring modification</span> </div> </a> <ul id="toc-C-_and_D-ring_modification-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-E-ring_modifications" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#E-ring_modifications"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>E-ring modifications</span> </div> </a> <ul id="toc-E-ring_modifications-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-CPT_analogues" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#CPT_analogues"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>CPT analogues</span> </div> </a> <ul id="toc-CPT_analogues-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biosynthesis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Biosynthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Biosynthesis</span> </div> </a> <ul id="toc-Biosynthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> 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</div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Camptothecin</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. 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href="https://fa.wikipedia.org/wiki/%DA%A9%D8%A7%D9%85%D9%BE%D8%AA%D9%88%D8%AA%D8%B3%DB%8C%D9%86" title="کامپتوتسین – Persian" lang="fa" hreflang="fa" data-title="کامپتوتسین" 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/Camptoth%C3%A9cine" title="Camptothécine – French" lang="fr" hreflang="fr" data-title="Camptothécine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Kamptotekin" title="Kamptotekin – Croatian" lang="hr" hreflang="hr" data-title="Kamptotekin" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Camptothecine" title="Camptothecine – Dutch" lang="nl" hreflang="nl" data-title="Camptothecine" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%AB%E3%83%B3%E3%83%97%E3%83%88%E3%83%86%E3%82%B7%E3%83%B3" title="カンプトテシン – Japanese" lang="ja" hreflang="ja" data-title="カンプトテシン" 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-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Camptotecin%C4%83" title="Camptotecină – Romanian" lang="ro" hreflang="ro" data-title="Camptotecină" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Kamptotecin" title="Kamptotecin – Serbian" lang="sr" hreflang="sr" data-title="Kamptotecin" 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/Kamptotecin" title="Kamptotecin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Kamptotecin" 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-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Kamptotesiini" title="Kamptotesiini – Finnish" lang="fi" hreflang="fi" data-title="Kamptotesiini" data-language-autonym="Suomi" data-language-local-name="Finnish" 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.infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Camptothecin">Camptothecin</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:Camptothecin.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ec/Camptothecin.svg/220px-Camptothecin.svg.png" decoding="async" width="220" height="142" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ec/Camptothecin.svg/330px-Camptothecin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ec/Camptothecin.svg/440px-Camptothecin.svg.png 2x" data-file-width="512" data-file-height="331" /></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/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</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>none</li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">(<i>S</i>)-4-ethyl-4-hydroxy-1<i>H</i>-pyrano[3',4':6,7]indolizino[1,2-b]<br />quinoline-3,14-(4<i>H</i>,12<i>H</i>)-dione</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=7689-03-4">7689-03-4</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/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/2538">2538</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/DB04690">DB04690</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.22775.html">22775</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/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/XT3Z54Z28A">XT3Z54Z28A</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/C01897">C01897</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/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:27656">CHEBI:27656</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/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL65">ChEMBL65</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/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/DTXSID0030956">DTXSID0030956</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q419964#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/100.113.172">100.113.172</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q419964#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>20</sub><span title="Hydrogen">H</span><sub>16</sub><span title="Nitrogen">N</span><sub>2</sub><span title="Oxygen">O</span><sub>4</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="7002348358000000000♠"></span>348.358</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=O%3DC%5C1N4%5CC%28%3DC%2FC2%3DC%2F1COC%28%3DO%29%5BC%40%5D2%28O%29CC%29c3nc5c%28cc3C4%29cccc5">Interactive image</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Melting_point" title="Melting point">Melting point</a></th><td class="infobox-data">275 to 277 °C (527 to 531 °F)</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%;">O=C\1N4\C(=C/C2=C/1COC(=O)[C@]2(O)CC)c3nc5c(cc3C4)cccc5</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/C20H16N2O4/c1-2-20(25)14-8-16-17-12(7-11-5-3-4-6-15(11)21-17)9-22(16)18(23)13(14)10-26-19(20)24/h3-8,25H,2,9-10H2,1H3/t20-/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></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:VSJKWCGYPAHWDS-FQEVSTJZSA-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></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">  <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=443672460&page2=Camptothecin">(verify)</a></span></span></td></tr></tbody></table> <p><b>Camptothecin</b> (<b>CPT</b>) is a <a href="/wiki/Topoisomerase_inhibitor" title="Topoisomerase inhibitor">topoisomerase inhibitor</a>. It was discovered in 1966 by M. E. Wall and M. C. Wani in systematic screening of <a href="/wiki/Natural_products" class="mw-redirect" title="Natural products">natural products</a> for anticancer <a href="/wiki/Drugs" class="mw-redirect" title="Drugs">drugs</a>. It was isolated from the <a href="/wiki/Bark_(botany)" title="Bark (botany)">bark</a> and <a href="/wiki/Plant_stem" title="Plant stem">stem</a> of <i><a href="/wiki/Camptotheca_acuminata" title="Camptotheca acuminata">Camptotheca acuminata</a></i> (Camptotheca, Happy tree), a <a href="/wiki/Tree" title="Tree">tree</a> native to <a href="/wiki/China" title="China">China</a> used in <a href="/wiki/Traditional_Chinese_medicine" title="Traditional Chinese medicine">traditional Chinese medicine</a>.<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> It has been used clinically in China for the treatment of gastrointestinal tumors.<sup id="cite_ref-Chemnetbase_3-0" class="reference"><a href="#cite_note-Chemnetbase-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> CPT showed anticancer activity in preliminary <a href="/wiki/Clinical_trials" class="mw-redirect" title="Clinical trials">clinical trials</a>, especially against breast, ovarian, colon, lung, and stomach cancers.<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> However, it has low <a href="/wiki/Solubility" title="Solubility">solubility</a> and adverse effects have been reported when used therapeutically,<sup id="cite_ref-Chemnetbase_3-1" class="reference"><a href="#cite_note-Chemnetbase-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> so synthetic and medicinal chemists have developed numerous syntheses of camptothecin<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><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><sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> and various derivatives to increase the benefits of the <a href="/wiki/Chemical" class="mw-redirect" title="Chemical">chemical</a>, with good results. Four CPT <a href="/wiki/Analog_(chemistry)" class="mw-redirect" title="Analog (chemistry)">analogues</a> have been approved and are used in <a href="/wiki/Cancer" title="Cancer">cancer</a> <a href="/wiki/Chemotherapy" title="Chemotherapy">chemotherapy</a><sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> today: <a href="/wiki/Topotecan" title="Topotecan">topotecan</a>, <a href="/wiki/Irinotecan" title="Irinotecan">irinotecan</a>, <a href="/wiki/Belotecan" title="Belotecan">belotecan</a>, and <a href="/wiki/Trastuzumab_deruxtecan" title="Trastuzumab deruxtecan">trastuzumab deruxtecan</a>.<sup id="cite_ref-M.E._Wall_1966_9-0" class="reference"><a href="#cite_note-M.E._Wall_1966-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-G._Samuelsson_2004_10-0" class="reference"><a href="#cite_note-G._Samuelsson_2004-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Camptothecin has also been found in other plants including <i><a href="/wiki/Chonemorpha_fragrans" title="Chonemorpha fragrans">Chonemorpha fragrans</a></i>.<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> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Structures">Structures</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Camptothecin&action=edit&section=1" title="Edit section: Structures"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>CPT has a planar pentacyclic ring <a href="/wiki/Structure" title="Structure">structure</a>, that includes a <a href="/wiki/Pyrrole" title="Pyrrole">pyrrolo</a>[3,4-β]-quinoline moiety (rings A, B and C), <a href="/wiki/Conjugated_system" title="Conjugated system">conjugated</a> <a href="/wiki/Pyridone" title="Pyridone">pyridone</a> moiety (ring D) and one <a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">chiral</a> center at position 20 within the <a href="/wiki/Alpha_carbon" class="mw-redirect" title="Alpha carbon">alpha-</a><a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxy</a> <a href="/wiki/Lactone" title="Lactone">lactone</a> ring with <a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">(S) configuration</a> (the E-ring). Its planar structure is thought to be one of the most important factors in topoisomerase inhibition.<sup id="cite_ref-H._Ulukan_2002_12-0" class="reference"><a href="#cite_note-H._Ulukan_2002-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-A.J._Lu_2002_13-0" class="reference"><a href="#cite_note-A.J._Lu_2002-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Camptothecin_binding.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Camptothecin_binding.svg/350px-Camptothecin_binding.svg.png" decoding="async" width="350" height="294" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Camptothecin_binding.svg/525px-Camptothecin_binding.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Camptothecin_binding.svg/700px-Camptothecin_binding.svg.png 2x" data-file-width="620" data-file-height="520" /></a><figcaption>Binding of CPT to topoisomerase I and DNA</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Binding">Binding</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Camptothecin&action=edit&section=2" title="Edit section: Binding"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>CPT binds to the topoisomerase I and DNA complex (the covalent complex) resulting in a ternary complex, and thereby stabilizing it. This prevents DNA re-ligation and therefore causes DNA damage which results in <a href="/wiki/Apoptosis" title="Apoptosis">apoptosis</a>.<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> CPT binds both to the enzyme and DNA with <a href="/wiki/Hydrogen_bonds" class="mw-redirect" title="Hydrogen bonds">hydrogen bonds</a>. The most important part of the structure is the E-ring which interacts from three different positions with the enzyme. The hydroxyl group in position 20 forms hydrogen bond to the side chain on <a href="/wiki/Aspartic_acid" title="Aspartic acid">aspartic acid</a> number <a href="/wiki/Peptide_sequence" class="mw-redirect" title="Peptide sequence">533</a> (Asp533) in the enzyme. It is critical that the <a href="/wiki/Molecular_configuration" title="Molecular configuration">configuration</a> of the chiral <a href="/wiki/Carbon" title="Carbon">carbon</a> is (S) because (R) is inactive. The lactone is bonded with two hydrogen bonds to the <a href="/wiki/Amino" class="mw-redirect" title="Amino">amino</a> groups on <a href="/wiki/Arginine" title="Arginine">arginine</a> 364 (Arg364). The D-ring interacts with the +1 <a href="/wiki/Cytosine" title="Cytosine">cytosine</a> on non-cleaved strand and stabilizes the topoisomerase I-DNA covalent complex by forming hydrogen bond. This hydrogen bond is between <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a> group in position 17 on the D-ring and amino group on the <a href="/wiki/Pyrimidine" title="Pyrimidine">pyrimidine</a> ring of +1 cytosine.<sup id="cite_ref-D.J.Adams_2005_15-0" class="reference"><a href="#cite_note-D.J.Adams_2005-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-M.R.Redinbo_1998_16-0" class="reference"><a href="#cite_note-M.R.Redinbo_1998-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> CPT is selectively cytotoxic to the cells replicating DNA during S phase <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> and its toxicity is primarily a result of conversion of single-strand breaks into double-strand breaks when the replication fork collides with the cleavage complexes formed by DNA and CPT.<sup id="cite_ref-Y.Pommier_2003_18-0" class="reference"><a href="#cite_note-Y.Pommier_2003-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Camptothecin&action=edit&section=3" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The lactone ring in CPT is highly susceptible to <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a>. The open ring form is inactive and it must therefore be closed to inhibit topoisomerase I. The closed form is favored in acidic condition, as it is in many cancer <a href="/wiki/Cell_(biology)" title="Cell (biology)">cells</a> microenvironment. CPT is transported into the cell by <a href="/wiki/Passive_transport" title="Passive transport">passive diffusion</a>. Cellular uptake is favored by <a href="/wiki/Lipophilicity" title="Lipophilicity">lipophilicity</a>, which enhances <a href="/wiki/Intracellular" class="mw-redirect" title="Intracellular">intracellular</a> accumulation. Lipophilicity makes <a href="/wiki/Chemical_compound" title="Chemical compound">compounds</a> more stable because of improved lactone partitioning into <a href="/wiki/Red_blood_cells" class="mw-redirect" title="Red blood cells">red blood cells</a> and consequently less hydrolysis of the lactone. CPT has affinity for human serum albumin (HSA), especially the carboxylate form of CPT. Because of that, the <a href="/wiki/Chemical_equilibrium" title="Chemical equilibrium">equilibrium</a> between the lactone ring and the carboxylate form is driven toward the carboxylate. Reduced drug-HSA <a href="/wiki/Drug_interaction" title="Drug interaction">interactions</a> could result in improved activity.<sup id="cite_ref-D.J.Adams_2005_15-1" class="reference"><a href="#cite_note-D.J.Adams_2005-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-F._Zunino_2002_19-0" class="reference"><a href="#cite_note-F._Zunino_2002-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Structure-activity_relationship">Structure-activity relationship</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Camptothecin&action=edit&section=4" title="Edit section: Structure-activity relationship"><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:Camptothecin_numbering.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/Camptothecin_numbering.svg/200px-Camptothecin_numbering.svg.png" decoding="async" width="200" height="149" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/Camptothecin_numbering.svg/300px-Camptothecin_numbering.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a1/Camptothecin_numbering.svg/400px-Camptothecin_numbering.svg.png 2x" data-file-width="658" data-file-height="489" /></a><figcaption>Camptothecin</figcaption></figure> <p>Studies have shown that <a href="/wiki/Substitution_(chemistry)" class="mw-redirect" title="Substitution (chemistry)">substitution</a> at position 7, 9, 10 and 11 can have positive effect on CPT activity and <a href="/wiki/Physical_properties" class="mw-redirect" title="Physical properties">physical properties</a>, e.g. potency and metabolic stability. Enlargement of the lactone ring by one <a href="/wiki/Methylene_bridge" title="Methylene bridge"><span class="chemf nowrap">CH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span> unit</a> also enhances its abilities, as in homocamptothecin. Substitution at position 12 and 14 leads to inactive derivative.<sup id="cite_ref-F._Zunino_2002_19-1" class="reference"><a href="#cite_note-F._Zunino_2002-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="A-_and_B-ring_modification">A- and B-ring modification</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Camptothecin&action=edit&section=5" title="Edit section: A- and B-ring modification"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Alkyl_substitution">Alkyl substitution</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Camptothecin&action=edit&section=6" title="Edit section: Alkyl substitution"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">Alkyl</a> substitution at position 7 has shown increased cytotoxicity, such as <a href="/wiki/Ethyl_group" title="Ethyl group">ethyl</a> (C<sub>2</sub>H<sub>5</sub>) or chloromethyl (CH<sub>2</sub>Cl). These groups are able to react with the DNA in the presence of topoisomerase I which leads to more <a href="/wiki/Tumor" class="mw-redirect" title="Tumor">tumor</a> activity. It has also been shown that increasing the length of the carbon chain (in position 7) leads to increased lipophilicity and consequently greater potency and stability in human <a href="/wiki/Blood_plasma" title="Blood plasma">plasma</a>.<sup id="cite_ref-D.J.Adams_2005_15-2" class="reference"><a href="#cite_note-D.J.Adams_2005-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-F._Zunino_2002_19-2" class="reference"><a href="#cite_note-F._Zunino_2002-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> Other 7-modified CPT analogues are silatecans and karenitecins. They are potent inhibitors on topoisomerase I and both have alkylsilyl groups in position 7 which make them lipophilic and more stable. Silatecans or 7-silylcampthothecins have shown reduced drug-HSA interactions which contributes to its blood stability and they can also cross the <a href="/wiki/Blood_brain_barrier" class="mw-redirect" title="Blood brain barrier">blood brain barrier</a>. DB-67 is a 10-hydroxy derivative and is among the most active silatecans. BNP1350 which belongs to the series of karenitecins exhibits cytotoxic activity and ability to overcome <a href="/wiki/Drug_resistance" title="Drug resistance">drug resistance</a>. Still another route to make CPT's lipophilic is to introduce lipophilic substituents, such as iminomethyl or oxyiminomethyl moieties. One of the most potent compounds is the oxyiminomethyl derivative ST1481 that has the advantage to overcome drug resistance caused by transport systems.<sup id="cite_ref-F._Zunino_2002_19-3" class="reference"><a href="#cite_note-F._Zunino_2002-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> Basic <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a> in a carbon chain at position 7 makes the compound more <a href="/wiki/Hydrophilic" class="mw-redirect" title="Hydrophilic">hydrophilic</a> and hence more water-soluble. For example, is a derivate called CKD-602, which is a potent topoisomerase I inhibitor and successfully overcomes the poor water solubility and toxicity seen with CPT.<sup id="cite_ref-F._Zunino_2002_19-4" class="reference"><a href="#cite_note-F._Zunino_2002-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-M._K._Chung_2006_20-0" class="reference"><a href="#cite_note-M._K._Chung_2006-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p><p>Considerably greater activity can be achieved by putting electron-withdrawing groups like amino, <a href="/wiki/Nitro_compound" title="Nitro compound">nitro</a>, <a href="/wiki/Bromine" title="Bromine">bromo</a> or <a href="/wiki/Chloro" class="mw-redirect" title="Chloro">chloro</a> at position 9 and 10 and hydroxyl group at position 10 or 11. But these compounds are relatively insoluble in aqueous solutions, which causes difficulty in administrations. <a href="/wiki/Methoxy" class="mw-redirect" title="Methoxy">Methoxy</a> group at both position 10 and 11 simultaneously leads to inactivity.<sup id="cite_ref-H._Ulukan_2002_12-1" class="reference"><a href="#cite_note-H._Ulukan_2002-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-F._Zunino_2002_19-5" class="reference"><a href="#cite_note-F._Zunino_2002-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Hexacyclic_CPT_analogues">Hexacyclic CPT analogues</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Camptothecin&action=edit&section=7" title="Edit section: Hexacyclic CPT analogues"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Hexacyclic CPT analogues have shown great potency. For example, <a href="/wiki/Methylenedioxy" title="Methylenedioxy">methylenedioxy</a> or ethylenedioxy group connected between 10 and 11 form a 5 or 6 membered ring which leads to more water-soluble derivates and increased potency. Researches have shown that ethylenedioxy analogues are less potent than methylenedioxy. The reason is the unfavorable steric interactions of ethylenedioxy analogues with the enzyme.<sup id="cite_ref-H._Ulukan_2002_12-2" class="reference"><a href="#cite_note-H._Ulukan_2002-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-F._Zunino_2002_19-6" class="reference"><a href="#cite_note-F._Zunino_2002-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p><p>Adding amino or chloro group at 9th position or chloromethyl group at 7th position to these 10, 11-methylenedioxy or ethylenedioxy analogues results in compounds with even greater cytotoxicity but weaker solubility in water. To yield 10, 11-methylenedioxy or ethylenedioxy analogues with good water solubility a good way is to introduce a water solubilising substituent at position 7. Lurtotecan meets those requirements; it's a 10, 11-ethylenedioxy analogue with a 4-methylpiperazino-methylene at position 7 and has shown a great potency in clinical researches.<sup id="cite_ref-H._Ulukan_2002_12-3" class="reference"><a href="#cite_note-H._Ulukan_2002-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p><p>A ring can also be formed between position 7 and 9, like position 10 and 11. That gives new opportunities to make water-soluble derivatives [5]. These hexacyclic CPT become more active when electron-withdrawing groups are put in position 11 and methyl or amino groups at 10. Exatecan is an example of hexacyclic CPT that has a 6 membered ring over position 7 and 9, and is 10-methyl, 11-fluoro substituted [4]. It is water-soluble and more potent than topotecan.<sup id="cite_ref-H._Ulukan_2002_12-4" class="reference"><a href="#cite_note-H._Ulukan_2002-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-F._Zunino_2002_19-7" class="reference"><a href="#cite_note-F._Zunino_2002-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-M._Palumbo_2001_21-0" class="reference"><a href="#cite_note-M._Palumbo_2001-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="C-_and_D-ring_modification">C- and D-ring modification</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Camptothecin&action=edit&section=8" title="Edit section: C- and D-ring modification"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The C- and D-rings have an essential role in the antitumor activity. Replacement in any position results in much less potent compound than parent compound in other cytotoxicity assay.<sup id="cite_ref-H._Ulukan_2002_12-5" class="reference"><a href="#cite_note-H._Ulukan_2002-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Homocamptothecin.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/76/Homocamptothecin.svg/250px-Homocamptothecin.svg.png" decoding="async" width="250" height="147" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/76/Homocamptothecin.svg/375px-Homocamptothecin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/76/Homocamptothecin.svg/500px-Homocamptothecin.svg.png 2x" data-file-width="512" data-file-height="302" /></a><figcaption>Homocamptothecin</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="E-ring_modifications">E-ring modifications</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Camptothecin&action=edit&section=9" title="Edit section: E-ring modifications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The E-ring doesn't allow many structural changes without losing CPT activity because it is necessary for binding to the active site of TOP I.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> One possible replacement is changing the hydroxyl group to Cl, F or Br because their <a href="/wiki/Polarizability" title="Polarizability">polarizability</a> is sufficient to stabilize the enzyme-complex.<sup id="cite_ref-F._Zunino_2002_19-8" class="reference"><a href="#cite_note-F._Zunino_2002-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p><p>Another possible modification is to insert a methylene between hydroxyl and lactone on the E-ring yielding a seven membered β-hydroxylactone group, so-called homocamptothecin (hCPT). The hCPT's hydroxyl has less <a href="/wiki/Inductive_effect" title="Inductive effect">inductive effect</a> on the carboxyl group which makes the lactone very reactive. This enhances the interaction of the free hydroxyl group optimally with topoisomerase I and the covalent complex that forms in its presence are more stable. The E-ring of hCPT opens more slowly and the opening is <a href="/wiki/Irreversibility" class="mw-redirect" title="Irreversibility">irreversible</a>. hCPTs exhibit enhanced human plasma stability because of decreased <a href="/wiki/Protein" title="Protein">protein</a> binding and more affinity for red blood cells than CPT.<sup id="cite_ref-H._Ulukan_2002_12-6" class="reference"><a href="#cite_note-H._Ulukan_2002-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-F._Zunino_2002_19-9" class="reference"><a href="#cite_note-F._Zunino_2002-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="CPT_analogues">CPT analogues</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Camptothecin&action=edit&section=10" title="Edit section: CPT analogues"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Since the discovery of CPT many analogues have been synthesized. Below is a schematic view of the CPT analogues that have been mentioned in the text above. </p> <div style="float:center; padding:0 0 0.5em 1.5em;"> <table class="wikitable" style="margin:0 auto;"> <tbody><tr> <td colspan="5"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Camptothecin_analogs.svg" class="mw-file-description" title="Camptothecin with radicals"><img alt="Camptothecin with radicals" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/35/Camptothecin_analogs.svg/280px-Camptothecin_analogs.svg.png" decoding="async" width="280" height="193" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/35/Camptothecin_analogs.svg/420px-Camptothecin_analogs.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/35/Camptothecin_analogs.svg/560px-Camptothecin_analogs.svg.png 2x" data-file-width="512" data-file-height="353" /></a><figcaption>Camptothecin with radicals</figcaption></figure> </td></tr> <tr> <td align="center"><b>Analogue</b> </td> <td align="center"><style data-mw-deduplicate="TemplateStyles:r1239334494">@media screen{html.skin-theme-clientpref-night .mw-parser-output div:not(.notheme)>.tmp-color,html.skin-theme-clientpref-night .mw-parser-output p>.tmp-color,html.skin-theme-clientpref-night .mw-parser-output table:not(.notheme) .tmp-color{color:inherit!important}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output div:not(.notheme)>.tmp-color,html.skin-theme-clientpref-os .mw-parser-output p>.tmp-color,html.skin-theme-clientpref-os .mw-parser-output table:not(.notheme) .tmp-color{color:inherit!important}}</style><span class="tmp-color" style="color:red"><b>R<sup>1</sup></b></span> </td> <td align="center"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:red"><b>R<sup>2</sup></b></span> </td> <td align="center"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:red"><b>R<sup>3</sup></b></span> </td> <td align="center"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:red"><b>R<sup>4</sup></b></span> </td></tr> <tr> <td><a href="/wiki/Topotecan" title="Topotecan">Topotecan</a> </td> <td align="center">—H </td> <td align="center"><span typeof="mw:File"><a href="/wiki/File:Topotecan_R2.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ef/Topotecan_R2.svg/69px-Topotecan_R2.svg.png" decoding="async" width="69" height="62" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ef/Topotecan_R2.svg/104px-Topotecan_R2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ef/Topotecan_R2.svg/138px-Topotecan_R2.svg.png 2x" data-file-width="512" data-file-height="460" /></a></span> </td> <td align="center">—OH </td> <td align="center">—H </td></tr> <tr> <td><a href="/wiki/Irinotecan" title="Irinotecan">Irinotecan</a> (CPT-11) </td> <td align="center"><span typeof="mw:File"><a href="/wiki/File:Irinotecan_R1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/94/Irinotecan_R1.svg/48px-Irinotecan_R1.svg.png" decoding="async" width="48" height="43" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/94/Irinotecan_R1.svg/72px-Irinotecan_R1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/94/Irinotecan_R1.svg/96px-Irinotecan_R1.svg.png 2x" data-file-width="512" data-file-height="463" /></a></span> </td> <td align="center">—H </td> <td align="center"><span typeof="mw:File"><a href="/wiki/File:Irinotecan_R3.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Irinotecan_R3.svg/190px-Irinotecan_R3.svg.png" decoding="async" width="190" height="71" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Irinotecan_R3.svg/285px-Irinotecan_R3.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/65/Irinotecan_R3.svg/380px-Irinotecan_R3.svg.png 2x" data-file-width="512" data-file-height="190" /></a></span> </td> <td align="center">—H </td></tr> <tr> <td><a href="/w/index.php?title=Silatecan&action=edit&redlink=1" class="new" title="Silatecan (page does not exist)">Silatecan</a> (DB-67, AR-67) </td> <td align="center"><span typeof="mw:File"><a href="/wiki/File:Silatecan_R1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/87/Silatecan_R1.svg/80px-Silatecan_R1.svg.png" decoding="async" width="80" height="58" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/87/Silatecan_R1.svg/120px-Silatecan_R1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/87/Silatecan_R1.svg/160px-Silatecan_R1.svg.png 2x" data-file-width="512" data-file-height="369" /></a></span> </td> <td align="center">—H </td> <td align="center">—OH </td> <td align="center">—H </td></tr> <tr> <td><a href="/w/index.php?title=Cositecan&action=edit&redlink=1" class="new" title="Cositecan (page does not exist)">Cositecan</a> (BNP-1350) </td> <td align="center"><span typeof="mw:File"><a href="/wiki/File:Cositecan_R1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/25/Cositecan_R1.svg/97px-Cositecan_R1.svg.png" decoding="async" width="97" height="69" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/25/Cositecan_R1.svg/146px-Cositecan_R1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/25/Cositecan_R1.svg/194px-Cositecan_R1.svg.png 2x" data-file-width="512" data-file-height="363" /></a></span> </td> <td align="center">—H </td> <td align="center">—H </td> <td align="center">—H </td></tr> <tr> <td><a href="/wiki/Exatecan" title="Exatecan">Exatecan</a> </td> <td colspan="2" align="center"><span typeof="mw:File"><a href="/wiki/File:Exatecan_R1R2.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/76/Exatecan_R1R2.svg/107px-Exatecan_R1R2.svg.png" decoding="async" width="107" height="55" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/76/Exatecan_R1R2.svg/161px-Exatecan_R1R2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/76/Exatecan_R1R2.svg/214px-Exatecan_R1R2.svg.png 2x" data-file-width="512" data-file-height="261" /></a></span> </td> <td align="center">—CH<sub>3</sub> </td> <td align="center">—F </td></tr> <tr> <td><a href="/wiki/Lurtotecan" title="Lurtotecan">Lurtotecan</a> </td> <td align="center"><span typeof="mw:File"><a href="/wiki/File:Lurtotecan_R1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/45/Lurtotecan_R1.svg/84px-Lurtotecan_R1.svg.png" decoding="async" width="84" height="105" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/45/Lurtotecan_R1.svg/126px-Lurtotecan_R1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/45/Lurtotecan_R1.svg/168px-Lurtotecan_R1.svg.png 2x" data-file-width="512" data-file-height="639" /></a></span> </td> <td align="center">—H </td> <td colspan="2" align="center"><span typeof="mw:File"><a href="/wiki/File:Lurtotecan_R3R4.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Lurtotecan_R3R4.svg/60px-Lurtotecan_R3R4.svg.png" decoding="async" width="60" height="71" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Lurtotecan_R3R4.svg/90px-Lurtotecan_R3R4.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Lurtotecan_R3R4.svg/120px-Lurtotecan_R3R4.svg.png 2x" data-file-width="512" data-file-height="605" /></a></span> </td></tr> <tr> <td><a href="/w/index.php?title=Gimatecan&action=edit&redlink=1" class="new" title="Gimatecan (page does not exist)">Gimatecan</a> (ST1481) </td> <td align="center"><span typeof="mw:File"><a href="/wiki/File:Gimatecan_R1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Gimatecan_R1.svg/97px-Gimatecan_R1.svg.png" decoding="async" width="97" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Gimatecan_R1.svg/146px-Gimatecan_R1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Gimatecan_R1.svg/194px-Gimatecan_R1.svg.png 2x" data-file-width="512" data-file-height="420" /></a></span> </td> <td align="center">—H </td> <td align="center">—H </td> <td align="center">—H </td></tr> <tr> <td><a href="/wiki/Belotecan" title="Belotecan">Belotecan</a> (CKD-602) </td> <td align="center"><span typeof="mw:File"><a href="/wiki/File:Belotecan_R1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Belotecan_R1.svg/101px-Belotecan_R1.svg.png" decoding="async" width="101" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Belotecan_R1.svg/152px-Belotecan_R1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Belotecan_R1.svg/202px-Belotecan_R1.svg.png 2x" data-file-width="512" data-file-height="406" /></a></span> </td> <td align="center">—H </td> <td align="center">—H </td> <td align="center">—H </td></tr> <tr> <td><a href="/wiki/Rubitecan" title="Rubitecan">Rubitecan</a> </td> <td align="center">—H </td> <td align="center"><span typeof="mw:File"><a href="/wiki/File:Rubitecan_R2.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Rubitecan_R2.svg/60px-Rubitecan_R2.svg.png" decoding="async" width="60" height="64" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Rubitecan_R2.svg/90px-Rubitecan_R2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Rubitecan_R2.svg/120px-Rubitecan_R2.svg.png 2x" data-file-width="512" data-file-height="546" /></a></span> </td> <td align="center">—H </td> <td align="center">—H </td></tr></tbody></table> </div> <p>CPT is linked to a <a href="/wiki/Cyclodextrin" title="Cyclodextrin">cyclodextrin</a>-based polymer to form the investigational anti-cancer drug <a href="/wiki/CRLX101" title="CRLX101">CRLX101</a>.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Biosynthesis">Biosynthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Camptothecin&action=edit&section=11" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:1_Tryptamine_biosynthesis_pathway.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/ff/1_Tryptamine_biosynthesis_pathway.png/220px-1_Tryptamine_biosynthesis_pathway.png" decoding="async" width="220" height="112" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/ff/1_Tryptamine_biosynthesis_pathway.png/330px-1_Tryptamine_biosynthesis_pathway.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/ff/1_Tryptamine_biosynthesis_pathway.png/440px-1_Tryptamine_biosynthesis_pathway.png 2x" data-file-width="2174" data-file-height="1106" /></a><figcaption>1 Tryptamine biosynthesis pathway</figcaption></figure> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:2_Secologanin_biosynthesis_pathway.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2c/2_Secologanin_biosynthesis_pathway.png/220px-2_Secologanin_biosynthesis_pathway.png" decoding="async" width="220" height="181" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2c/2_Secologanin_biosynthesis_pathway.png/330px-2_Secologanin_biosynthesis_pathway.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2c/2_Secologanin_biosynthesis_pathway.png/440px-2_Secologanin_biosynthesis_pathway.png 2x" data-file-width="2210" data-file-height="1816" /></a><figcaption>2 Secologanin biosynthesis pathway</figcaption></figure> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Tryptamine_and_strictosidine_to_camptothecin.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2a/Tryptamine_and_strictosidine_to_camptothecin.png/220px-Tryptamine_and_strictosidine_to_camptothecin.png" decoding="async" width="220" height="101" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2a/Tryptamine_and_strictosidine_to_camptothecin.png/330px-Tryptamine_and_strictosidine_to_camptothecin.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2a/Tryptamine_and_strictosidine_to_camptothecin.png/440px-Tryptamine_and_strictosidine_to_camptothecin.png 2x" data-file-width="2207" data-file-height="1010" /></a><figcaption>Tryptamine and strictosidine to camptothecin</figcaption></figure> <p>Like all other monoterpenoid indole-alkaloids, biosynthesis of camptothecin requires production of the <a href="/wiki/Strictosidine" title="Strictosidine">strictosidine</a>. Strictosidine is synthesized through condensation reaction between tryptamine from shikimate pathway and secologanin from either mevalonate (MVA) pathway or non-mevalonate pathway (MEP).<sup id="cite_ref-YamazakiKitajima2004_24-0" class="reference"><a href="#cite_note-YamazakiKitajima2004-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> Strictosidine then undergoes intermolecular cyclization to produce strictosamide, which is converted to camptothecin through a series of oxidation reactions by enzymes that still needs to be resolved.<sup id="cite_ref-LorenceNessler2004_25-0" class="reference"><a href="#cite_note-LorenceNessler2004-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p><p>The shikimate pathway leading to biosynthesis of tryptamine is mostly understood. First, chorismate is converted to anthranilate by the alpha-subunit of anthranilate synthase (ASA). Anthranilate reacts with 5-phosphoribose pyrophosphate to produce 5-phosphoribosylanthranilate. Then this intermediate is converted to indole glycerol phosphate, which interacts with the alpha-subunit of tryptophan (TSA) synthase to yield indole. The beta-subunit of tryptophan synthase (TSB) catalyzes condensation of indole with serine, leading to tryptophan. In the next step, tryptamine is produced as the result of decarboxylation by tryptophan decarboxylase (TDC).<sup id="cite_ref-New_Light_26-0" class="reference"><a href="#cite_note-New_Light-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p><p>Secologanin synthesis begins with condensation reaction between pyruvate and D-Glyceraldehyde-3-phosphate catalyzed by 1-deoxy-D-xylulose-5-phosphate synthase (DXS) to produce 1-deoxy-D-xylulose-5-phosphate (DXP). The conversion of DXP to isopentenyl diphosphate (IPP), which is the common terpenoid biosynthesis precursor involves 1-deoxy-D-xylulose-5-phosphate reductoisomerase (DXR) and 1-hydroxy-2-methyl-2(E)-butenyl-4-diphosphate reductase (HDR). The formation of IPP can be achieved by both MVA and MEP pathways.<sup id="cite_ref-New_Light_26-1" class="reference"><a href="#cite_note-New_Light-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> Condensation of IPP and dimethylallyl diphosphate (DMAPP) yields geranyl diphosphate (GPP). The geraniol synthase (GS) then converts GPP to geraniol.<sup id="cite_ref-YamazakiKitajima2004_24-1" class="reference"><a href="#cite_note-YamazakiKitajima2004-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> The conversion of geraniol to secologanin occurs through various enzymatic reactions. Based on studies with radioactive labelling and pathway specific inhibitors, MEP pathway is the primary source for secologanin.<sup id="cite_ref-New_Light_26-2" class="reference"><a href="#cite_note-New_Light-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> Tryptamine from shikimate pathway and secologanin from MVA or MEP pathway are converted to strictosidine through a condensation reaction catalyzed by strictosidine synthase. Although it is not fully resolved, it has been postulated that camptothecin is produced from strictosidine via strictosamide, 3 (S)-pumiloside and 3 (S)-deoxypumiloside.<sup id="cite_ref-LorenceNessler2004_25-1" class="reference"><a href="#cite_note-LorenceNessler2004-25"><span class="cite-bracket">[</span>25<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=Camptothecin&action=edit&section=12" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width reflist-columns-2"> <ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFGovindachariViswnathan1972" class="citation journal cs1">Govindachari TR, Viswnathan N (1972). 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Academic Press. 27 July 2013. pp. 143–149. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-08-099411-6" title="Special:BookSources/978-0-08-099411-6"><bdi>978-0-08-099411-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=New+Light+on+Alkaloid+Biosynthesis+and+Future+Prospects&rft.pages=143-149&rft.pub=Academic+Press&rft.date=2013-07-27&rft.isbn=978-0-08-099411-6&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DbaP3IV_DdaAC%26pg%3DPA143&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACamptothecin" class="Z3988"></span></span> </li> </ol></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist 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code L01">L01</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Spindle_poison" title="Spindle poison">SPs</a>/<a href="/wiki/Mitotic_inhibitor" title="Mitotic inhibitor">MIs</a><br />(<a href="/wiki/M_phase" class="mw-redirect" title="M phase">M phase</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Block <a href="/wiki/Microtubule" title="Microtubule">microtubule</a> assembly</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Vinca_alkaloid" title="Vinca alkaloid">Vinca alkaloids</a></i> (<a href="/wiki/Vinblastine" title="Vinblastine">Vinblastine</a><sup>#</sup></li> <li><a href="/wiki/Vincristine" title="Vincristine">Vincristine</a><sup>#</sup></li> <li><a href="/wiki/Vindesine" title="Vindesine">Vindesine</a></li> <li><a href="/wiki/Vinflunine" title="Vinflunine">Vinflunine</a><sup>§</sup></li> <li><a href="/wiki/Vinorelbine" title="Vinorelbine">Vinorelbine</a><sup>#</sup>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Block microtubule disassembly</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Taxane" title="Taxane">Taxanes</a></i> (<a href="/wiki/Cabazitaxel" title="Cabazitaxel">Cabazitaxel</a></li> <li><a href="/wiki/Docetaxel" title="Docetaxel">Docetaxel</a><sup>#</sup></li> <li><a href="/wiki/Larotaxel" title="Larotaxel">Larotaxel</a></li> <li><a href="/wiki/Ortataxel" title="Ortataxel">Ortataxel</a><sup>†</sup></li> <li><a href="/wiki/Paclitaxel" title="Paclitaxel">Paclitaxel</a><sup>#</sup></li> <li><a href="/wiki/Tesetaxel" title="Tesetaxel">Tesetaxel</a>)</li> <li><i><a href="/wiki/Epothilone" title="Epothilone">Epothilones</a></i> (<a href="/wiki/Ixabepilone" title="Ixabepilone">Ixabepilone</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/DNA_replication" title="DNA replication">DNA replication</a><br />inhibitor</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">DNA precursors/<br /><a href="/wiki/Antimetabolite" title="Antimetabolite">antimetabolites</a><br />(<a href="/wiki/S_phase" title="S phase">S phase</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antifolate" title="Antifolate">Folic acid</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Dihydrofolate_reductase_inhibitor" title="Dihydrofolate reductase inhibitor">Dihydrofolate reductase inhibitor</a></i> (<a href="/wiki/Aminopterin" title="Aminopterin">Aminopterin</a></li> <li><a href="/wiki/Methotrexate" title="Methotrexate">Methotrexate</a><sup>#</sup></li> <li><a href="/wiki/Pemetrexed" title="Pemetrexed">Pemetrexed</a></li> <li><a href="/wiki/Pralatrexate" title="Pralatrexate">Pralatrexate</a>)</li> <li><i><a href="/wiki/Thymidylate_synthase_inhibitor" title="Thymidylate synthase inhibitor">Thymidylate synthase inhibitor</a></i> (<a href="/wiki/Pemetrexed" title="Pemetrexed">Pemetrexed</a></li> <li><a href="/wiki/Raltitrexed" title="Raltitrexed">Raltitrexed</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Purine_analogue" title="Purine analogue">Purine</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Adenosine_deaminase_inhibitor" class="mw-redirect" title="Adenosine deaminase inhibitor">Adenosine deaminase inhibitor</a></i> (<a href="/wiki/Pentostatin" title="Pentostatin">Pentostatin</a>)</li></ul> <ul><li><i><a href="/wiki/Halogenation" title="Halogenation">Halogenated</a>/<a href="/wiki/Ribonucleotide_reductase_inhibitor" title="Ribonucleotide reductase inhibitor">ribonucleotide reductase inhibitors</a></i> (<a href="/wiki/Cladribine" title="Cladribine">Cladribine</a></li> <li><a href="/wiki/Clofarabine" title="Clofarabine">Clofarabine</a></li> <li><a href="/wiki/Fludarabine" title="Fludarabine">Fludarabine</a>)</li> <li><a href="/wiki/Nelarabine" title="Nelarabine">Nelarabine</a></li> <li><a href="/wiki/Rabacfosadine" title="Rabacfosadine">Rabacfosadine</a></li> <li><i><a href="/wiki/Thiopurine" title="Thiopurine">Thiopurine</a></i> (<a href="/wiki/Mercaptopurine" title="Mercaptopurine">Mercaptopurine</a><sup>#</sup></li> <li><a href="/wiki/Tioguanine" title="Tioguanine">Tioguanine</a><sup>#</sup>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pyrimidine_analogue" title="Pyrimidine analogue">Pyrimidine</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Thymidylate_synthase_inhibitor" title="Thymidylate synthase inhibitor">Thymidylate synthase inhibitor</a></i> (<a href="/wiki/Capecitabine" title="Capecitabine">Capecitabine</a><sup>#</sup></li> <li><a href="/wiki/Carmofur" title="Carmofur">Carmofur</a></li> <li><a href="/wiki/Doxifluridine" title="Doxifluridine">Doxifluridine</a></li> <li><a href="/wiki/Floxuridine" title="Floxuridine">Floxuridine</a></li> <li><a href="/wiki/Fluorouracil" title="Fluorouracil">Fluorouracil</a><sup>#</sup></li> <li><a href="/wiki/Tegafur" title="Tegafur">Tegafur</a> (<a href="/wiki/Tegafur/gimeracil/oteracil" title="Tegafur/gimeracil/oteracil">+gimeracil/oteracil</a>))</li></ul> <ul><li><i><a href="/wiki/DNA_polymerase_inhibitor" class="mw-redirect" title="DNA polymerase inhibitor">DNA polymerase inhibitor</a></i> (<a href="/wiki/Cytarabine" title="Cytarabine">Cytarabine</a><sup>#</sup> <a href="/wiki/Daunorubicin/cytarabine" title="Daunorubicin/cytarabine">+daunorubicin</a>)</li></ul> <ul><li><i><a href="/wiki/Ribonucleotide_reductase_inhibitor" title="Ribonucleotide reductase inhibitor">Ribonucleotide reductase inhibitor</a></i> (<a href="/wiki/Gemcitabine" title="Gemcitabine">Gemcitabine</a><sup>#</sup>)</li></ul> <ul><li><i><a href="/wiki/Hypomethylating_agent" title="Hypomethylating agent">Hypomethylating agent</a></i> (<a href="/wiki/Azacitidine" title="Azacitidine">Azacitidine</a></li> <li><a href="/wiki/Decitabine" title="Decitabine">Decitabine</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Deoxyribonucleotide" title="Deoxyribonucleotide">Deoxyribonucleotide</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Ribonucleotide_reductase_inhibitor" title="Ribonucleotide reductase inhibitor">Ribonucleotide reductase inhibitor</a></i> (<a href="/wiki/Hydroxycarbamide" title="Hydroxycarbamide">Hydroxycarbamide</a><sup>#</sup>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Topoisomerase_inhibitor" title="Topoisomerase inhibitor">Topoisomerase inhibitors</a><br />(<a href="/wiki/S_phase" title="S phase">S phase</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Type_I_topoisomerase#Inhibition" title="Type I topoisomerase">I</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Camptotheca" title="Camptotheca">Camptotheca</a></i> (<a href="/wiki/Belotecan" title="Belotecan">Belotecan</a></li> <li><a class="mw-selflink selflink">Camptothecin</a></li> <li><a href="/w/index.php?title=Cositecan&action=edit&redlink=1" class="new" title="Cositecan (page does not exist)">Cositecan</a><sup>†</sup></li> <li><a href="/wiki/Etirinotecan_pegol" title="Etirinotecan pegol">Etirinotecan pegol</a><sup>†</sup></li> <li><a href="/wiki/Exatecan" title="Exatecan">Exatecan</a></li> <li><a href="/w/index.php?title=Gimatecan&action=edit&redlink=1" class="new" title="Gimatecan (page does not exist)">Gimatecan</a></li> <li><a href="/wiki/Irinotecan" title="Irinotecan">Irinotecan</a><sup>#</sup></li> <li><a href="/wiki/Lurtotecan" title="Lurtotecan">Lurtotecan</a><sup>‡</sup></li> <li><a href="/wiki/Rubitecan" title="Rubitecan">Rubitecan</a><sup>‡</sup></li> <li><a href="/w/index.php?title=Silatecan&action=edit&redlink=1" class="new" title="Silatecan (page does not exist)">Silatecan</a><sup>§</sup></li> <li><a href="/wiki/Topotecan" title="Topotecan">Topotecan</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Type_II_topoisomerase#Inhibition" title="Type II topoisomerase">II</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Podophyllum_peltatum" title="Podophyllum peltatum">Podophyllum</a></i> (<a href="/wiki/Etoposide" title="Etoposide">Etoposide</a><sup>#</sup></li> <li><a href="/wiki/Teniposide" title="Teniposide">Teniposide</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Type_II_topoisomerase#Inhibition" title="Type II topoisomerase">II</a>+<a href="/wiki/Intercalation_(biochemistry)" title="Intercalation (biochemistry)">Intercalation</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Anthracycline" title="Anthracycline">Anthracyclines</a></i> (<a href="/wiki/Aclarubicin" title="Aclarubicin">Aclarubicin</a></li> <li><a href="/wiki/Amrubicin" title="Amrubicin">Amrubicin</a><sup>†</sup></li> <li><a href="/wiki/Daunorubicin" title="Daunorubicin">Daunorubicin</a><sup>#</sup> (<a href="/wiki/Daunorubicin/cytarabine" title="Daunorubicin/cytarabine">+cytarabine</a>)</li> <li><a href="/wiki/Doxorubicin" title="Doxorubicin">Doxorubicin</a><sup>#</sup></li> <li><a href="/wiki/Epirubicin" title="Epirubicin">Epirubicin</a></li> <li><a href="/wiki/Idarubicin" title="Idarubicin">Idarubicin</a></li> <li><a href="/wiki/Pirarubicin" title="Pirarubicin">Pirarubicin</a></li> <li><a href="/wiki/Valrubicin" title="Valrubicin">Valrubicin</a></li> <li><a href="/wiki/Zorubicin" title="Zorubicin">Zorubicin</a>)</li> <li><i><a href="/wiki/Anthraquinone" title="Anthraquinone">Anthracenediones</a></i> (<a href="/wiki/Losoxantrone" title="Losoxantrone">Losoxantrone</a></li> <li><a href="/wiki/Mitoxantrone" title="Mitoxantrone">Mitoxantrone</a></li> <li><a href="/wiki/Pixantrone" title="Pixantrone">Pixantrone</a>)</li> <li><a href="/wiki/Amsacrine" title="Amsacrine">Amsacrine</a></li> <li><a href="/wiki/Bisantrene" title="Bisantrene">Bisantrene</a></li> <li><a href="/wiki/Crisnatol" title="Crisnatol">Crisnatol</a></li> <li><a href="/wiki/Menogaril" title="Menogaril">Menogaril</a><sup>§</sup></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Crosslinking_of_DNA" title="Crosslinking of DNA">Crosslinking of DNA</a><br />(<a href="/wiki/Cell-cycle_nonspecific_antineoplastic_agents" title="Cell-cycle nonspecific antineoplastic agents">CCNS</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Alkylating_antineoplastic_agent" title="Alkylating antineoplastic agent">Alkylating</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Nitrogen_mustard" title="Nitrogen mustard">Nitrogen mustards</a>:</i> <a href="/wiki/Bendamustine" title="Bendamustine">Bendamustine</a><sup>#</sup></li> <li><a href="/wiki/Chlormethine" title="Chlormethine">Chlormethine</a></li> <li><a href="/wiki/Cyclophosphamide" title="Cyclophosphamide">Cyclophosphamide</a><sup>#</sup> (<a href="/wiki/Ifosfamide" title="Ifosfamide">Ifosfamide</a><sup>#</sup></li> <li><a href="/wiki/Trofosfamide" title="Trofosfamide">Trofosfamide</a>)</li> <li><a href="/wiki/Chlorambucil" title="Chlorambucil">Chlorambucil</a><sup>#</sup></li> <li><a href="/wiki/Melphalan" title="Melphalan">Melphalan</a> (<a href="/wiki/Melphalan_flufenamide" title="Melphalan flufenamide">Melphalan flufenamide</a>)</li> <li><a href="/wiki/Prednimustine" title="Prednimustine">Prednimustine</a></li> <li><a href="/wiki/Uramustine" title="Uramustine">Uramustine</a></li></ul> <ul><li><i><a href="/wiki/Nitrosourea" title="Nitrosourea">Nitrosoureas</a>:</i> <a href="/wiki/Carmustine" title="Carmustine">Carmustine</a></li> <li><a href="/wiki/Fotemustine" title="Fotemustine">Fotemustine</a></li> <li><a href="/wiki/Lomustine" title="Lomustine">Lomustine</a> (<a href="/wiki/Semustine" title="Semustine">Semustine</a>)</li> <li><a href="/wiki/Nimustine" title="Nimustine">Nimustine</a></li> <li><a href="/wiki/Ranimustine" title="Ranimustine">Ranimustine</a></li> <li><a href="/wiki/Streptozotocin" title="Streptozotocin">Streptozocin</a></li></ul> <ul><li><i><a href="/wiki/Alkyl_sulfonate" title="Alkyl sulfonate">Alkyl sulfonates</a>:</i> <a href="/wiki/Busulfan" title="Busulfan">Busulfan</a> (<a href="/wiki/Mannosulfan" title="Mannosulfan">Mannosulfan</a></li> <li><a href="/wiki/Treosulfan" title="Treosulfan">Treosulfan</a>)</li></ul> <ul><li><i><a href="/wiki/Aziridine" title="Aziridine">Aziridines</a>:</i> <a href="/wiki/Carboquone" title="Carboquone">Carboquone</a></li> <li><a href="/wiki/Thiotepa" title="Thiotepa">Thiotepa</a></li> <li><a href="/wiki/Triaziquone" title="Triaziquone">Triaziquone</a></li> <li><a href="/wiki/Triethylenemelamine" title="Triethylenemelamine">Triethylenemelamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Platinum-based_antineoplastic" title="Platinum-based antineoplastic">Platinum-based</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carboplatin" title="Carboplatin">Carboplatin</a><sup>#</sup></li> <li><a href="/wiki/Cisplatin" title="Cisplatin">Cisplatin</a><sup>#</sup></li> <li><a href="/wiki/Dicycloplatin" title="Dicycloplatin">Dicycloplatin</a></li> <li><a href="/wiki/Nedaplatin" title="Nedaplatin">Nedaplatin</a></li> <li><a href="/wiki/Oxaliplatin" title="Oxaliplatin">Oxaliplatin</a><sup>#</sup></li> <li><a href="/wiki/Satraplatin" title="Satraplatin">Satraplatin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Alkylating_antineoplastic_agent#Nonclassical" title="Alkylating antineoplastic agent">Nonclassical</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Altretamine" title="Altretamine">Altretamine</a></li> <li><i><a href="/wiki/Hydrazine" title="Hydrazine">Hydrazines</a></i> (<a href="/wiki/Procarbazine" title="Procarbazine">Procarbazine</a><sup>#</sup>)</li> <li><a href="/wiki/Etoglucid" title="Etoglucid">Etoglucid</a></li> <li><a href="/wiki/Mitobronitol" title="Mitobronitol">Mitobronitol</a></li> <li><a href="/wiki/Pipobroman" title="Pipobroman">Pipobroman</a></li> <li><i><a href="/wiki/Triazene" title="Triazene">Triazenes</a></i> (<a href="/wiki/Dacarbazine" title="Dacarbazine">Dacarbazine</a><sup>#</sup></li> <li><a href="/wiki/Mitozolomide" title="Mitozolomide">Mitozolomide</a><sup>§</sup></li> <li><a href="/wiki/Temozolomide" title="Temozolomide">Temozolomide</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Intercalation_(biochemistry)" title="Intercalation (biochemistry)">Intercalation</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Streptomyces" title="Streptomyces">Streptomyces</a> (<a href="/wiki/Dactinomycin" title="Dactinomycin">Dactinomycin</a><sup>#</sup></li> <li><a href="/wiki/Bleomycin" title="Bleomycin">Bleomycin</a><sup>#</sup></li> <li><a href="/wiki/Mitomycins" title="Mitomycins">Mitomycins</a></li> <li><a href="/wiki/Plicamycin" title="Plicamycin">Plicamycin</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Photosensitizer" title="Photosensitizer">Photosensitizers</a>/<a href="/wiki/Photodynamic_therapy" title="Photodynamic therapy">PDT</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/Aminolevulinic_acid" title="Aminolevulinic acid">Aminolevulinic acid</a></li> <li><a href="/wiki/Efaproxiral" title="Efaproxiral">Efaproxiral</a></li> <li><a href="/wiki/Methyl_aminolevulinate" title="Methyl aminolevulinate">Methyl aminolevulinate</a></li> <li><a href="/wiki/Padeliporfin" title="Padeliporfin">Padeliporfin</a></li> <li><i><a href="/wiki/Porphyrin" title="Porphyrin">Porphyrin derivatives</a></i> (<a href="/wiki/Porfimer_sodium" title="Porfimer sodium">Porfimer sodium</a></li> <li><a href="/wiki/Talaporfin" title="Talaporfin">Talaporfin</a></li> <li><a href="/wiki/Temoporfin" title="Temoporfin">Temoporfin</a></li> <li><a href="/wiki/Verteporfin" title="Verteporfin">Verteporfin</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"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">Enzyme inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Farnesyltransferase_inhibitor" title="Farnesyltransferase inhibitor">FI</a></i> (<a href="/wiki/Tipifarnib" title="Tipifarnib">Tipifarnib</a><sup>§</sup>)</li> <li><i><a href="/wiki/Cyclin-dependent_kinase" title="Cyclin-dependent kinase">CDK</a> <a href="/wiki/Protein_kinase_inhibitor" title="Protein kinase inhibitor">inhibitors</a></i> (<a href="/wiki/Abemaciclib" title="Abemaciclib">Abemaciclib</a></li> <li><a href="/wiki/Alvocidib" title="Alvocidib">Alvocidib</a><sup>†</sup></li> <li><a href="/wiki/Palbociclib" title="Palbociclib">Palbociclib</a></li> <li><a href="/wiki/Ribociclib" title="Ribociclib">Ribociclib</a></li> <li><a href="/wiki/Seliciclib" title="Seliciclib">Seliciclib</a><sup>†</sup>)</li> <li><i><a href="/wiki/Proteasome_inhibitor" title="Proteasome inhibitor">PrI</a></i> <ul><li><a href="/wiki/Bortezomib" title="Bortezomib">Bortezomib</a></li> <li><a href="/wiki/Carfilzomib" title="Carfilzomib">Carfilzomib</a></li> <li><a href="/wiki/Oprozomib" title="Oprozomib">Oprozomib</a></li> <li><a href="/wiki/Ixazomib" title="Ixazomib">Ixazomib</a></li></ul></li> <li><i><a href="/wiki/Phosphodiesterase_inhibitor" title="Phosphodiesterase inhibitor">PhI</a></i> (<a href="/wiki/Anagrelide" title="Anagrelide">Anagrelide</a>)</li> <li><i><a href="/wiki/IMP_dehydrogenase" class="mw-redirect" title="IMP dehydrogenase">IMPDI</a></i> (<a href="/wiki/Tiazofurin" title="Tiazofurin">Tiazofurin</a><sup>§</sup>)</li> <li><i><a href="/wiki/Lipoxygenase_inhibitor" class="mw-redirect" title="Lipoxygenase inhibitor">LI</a></i> (<a href="/wiki/Masoprocol" title="Masoprocol">Masoprocol</a>)</li> <li><i><a href="/wiki/PARP_inhibitor" title="PARP inhibitor">PARP inhibitor</a></i> (<a href="/wiki/Fuzuloparib" title="Fuzuloparib">Fuzuloparib</a></li> <li><a href="/wiki/Niraparib" title="Niraparib">Niraparib</a> <a href="/wiki/Niraparib/abiraterone_acetate" title="Niraparib/abiraterone acetate">+abiraterone acetate</a></li> <li><a href="/wiki/Olaparib" title="Olaparib">Olaparib</a></li> <li><a href="/wiki/Rucaparib" title="Rucaparib">Rucaparib</a>)</li> <li><i><a href="/wiki/Histone_deacetylase_inhibitor" title="Histone deacetylase inhibitor">HDAC</a></i> (<a href="/wiki/Belinostat" title="Belinostat">Belinostat</a></li> <li><a href="/wiki/Entinostat" title="Entinostat">Entinostat</a></li> <li><a href="/wiki/Panobinostat" title="Panobinostat">Panobinostat</a></li> <li><a href="/wiki/Romidepsin" title="Romidepsin">Romidepsin</a></li> <li><a href="/wiki/Vorinostat" title="Vorinostat">Vorinostat</a>)</li> <li><i><a href="/wiki/Phosphoinositide_3-kinase_inhibitor" title="Phosphoinositide 3-kinase inhibitor">PIKI</a> (Pi3K)</i> (<a href="/wiki/Alpelisib" title="Alpelisib">Alpelisib</a></li> <li><a href="/wiki/Copanlisib" title="Copanlisib">Copanlisib</a><sup>‡</sup></li> <li><a href="/wiki/Duvelisib" title="Duvelisib">Duvelisib</a></li> <li><a href="/wiki/Idelalisib" title="Idelalisib">Idelalisib</a></li> <li><a href="/wiki/Inavolisib" title="Inavolisib">Inavolisib</a></li> <li><a href="/wiki/Umbralisib" title="Umbralisib">Umbralisib</a><sup>‡</sup>)</li> <li><i><a href="/wiki/Isocitrate_dehydrogenase" title="Isocitrate dehydrogenase">IDH</a></i> (<a href="/wiki/Enasidenib" title="Enasidenib">Enasidenib</a></li> <li><a href="/wiki/Ivosidenib" title="Ivosidenib">Ivosidenib</a></li> <li><a href="/wiki/Olutasidenib" title="Olutasidenib">Olutasidenib</a></li> <li><a href="/wiki/Vorasidenib" title="Vorasidenib">Vorasidenib</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Receptor_antagonist" title="Receptor antagonist">Receptor antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Endothelin_receptor_antagonist" title="Endothelin receptor antagonist">ERA</a></i> (<a href="/wiki/Atrasentan" title="Atrasentan">Atrasentan</a>)</li> <li><i><a href="/wiki/Retinoid_X_receptor" title="Retinoid X receptor">Retinoid X receptor</a></i> (<a href="/wiki/Bexarotene" title="Bexarotene">Bexarotene</a>)</li> <li><i><a href="/wiki/Sex_steroid" class="mw-redirect" title="Sex steroid">Sex steroid</a></i> (<a href="/wiki/Testolactone" title="Testolactone">Testolactone</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other/ungrouped</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adagrasib" title="Adagrasib">Adagrasib</a></li> <li><a href="/wiki/Aflibercept" title="Aflibercept">Aflibercept</a></li> <li><a href="/wiki/Arsenic_trioxide" title="Arsenic trioxide">Arsenic trioxide</a></li> <li><i><a href="/wiki/Asparagine" title="Asparagine">Asparagine depleters</a></i> (<a href="/wiki/Asparaginase" title="Asparaginase">Asparaginase</a><sup>#</sup>/<a href="/wiki/Pegaspargase" title="Pegaspargase">Pegaspargase</a>)</li> <li><a href="/wiki/Axicabtagene_ciloleucel" title="Axicabtagene ciloleucel">Axicabtagene ciloleucel</a></li> <li><a href="/wiki/Belzutifan" title="Belzutifan">Belzutifan</a></li> <li><a href="/wiki/Bexarotene" title="Bexarotene">Bexarotene</a></li> <li><a href="/wiki/Brexucabtagene_autoleucel" title="Brexucabtagene autoleucel">Brexucabtagene autoleucel</a></li> <li><a href="/wiki/Celecoxib" title="Celecoxib">Celecoxib</a></li> <li><a href="/wiki/Ciltacabtagene_autoleucel" title="Ciltacabtagene autoleucel">Ciltacabtagene autoleucel</a></li> <li><a href="/wiki/Demecolcine" title="Demecolcine">Demecolcine</a></li> <li><a href="/wiki/Denileukin_diftitox" title="Denileukin diftitox">Denileukin diftitox</a></li> <li><a href="/wiki/Eflornithine" title="Eflornithine">Eflornithine</a></li> <li><a href="/wiki/Elesclomol" title="Elesclomol">Elesclomol</a><sup>§</sup></li> <li><a href="/wiki/Elsamitrucin" title="Elsamitrucin">Elsamitrucin</a></li> <li><a href="/wiki/Epacadostat" title="Epacadostat">Epacadostat</a></li> <li><a href="/wiki/Eribulin" title="Eribulin">Eribulin</a></li> <li><a href="/wiki/Estramustine_phosphate" title="Estramustine phosphate">Estramustine</a></li> <li><a href="/wiki/Glasdegib" title="Glasdegib">Glasdegib</a></li> <li><a href="/wiki/Idecabtagene_vicleucel" title="Idecabtagene vicleucel">Idecabtagene vicleucel</a></li> <li><a href="/wiki/Imetelstat" title="Imetelstat">Imetelstat</a></li> <li><a href="/wiki/Lifileucel" title="Lifileucel">Lifileucel</a></li> <li><a href="/wiki/Lisocabtagene_maraleucel" title="Lisocabtagene maraleucel">Lisocabtagene maraleucel</a></li> <li><a href="/wiki/Lonidamine" title="Lonidamine">Lonidamine</a></li> <li><a href="/wiki/Lucanthone" title="Lucanthone">Lucanthone</a></li> <li><a href="/wiki/Lurbinectedin" title="Lurbinectedin">Lurbinectedin</a></li> <li><a href="/wiki/Mitoguazone" title="Mitoguazone">Mitoguazone</a></li> <li><a href="/wiki/Mitotane" title="Mitotane">Mitotane</a></li> <li><a href="/wiki/Nadofaragene_firadenovec" title="Nadofaragene firadenovec">Nadofaragene firadenovec</a></li> <li><a href="/wiki/Navitoclax" title="Navitoclax">Navitoclax</a></li> <li><a href="/wiki/Obecabtagene_autoleucel" title="Obecabtagene autoleucel">Obecabtagene autoleucel</a></li> <li><a href="/wiki/Oblimersen" title="Oblimersen">Oblimersen</a><sup>†</sup></li> <li><a href="/wiki/Omacetaxine_mepesuccinate" title="Omacetaxine mepesuccinate">Omacetaxine mepesuccinate</a></li> <li><a href="/wiki/Plitidepsin" title="Plitidepsin">Plitidepsin</a></li> <li><a href="/wiki/Tabelecleucel" title="Tabelecleucel">Tabelecleucel</a></li> <li><i><a href="/wiki/Retinoid" title="Retinoid">Retinoids</a></i> (<a href="/wiki/Alitretinoin" title="Alitretinoin">Alitretinoin</a></li> <li><a href="/wiki/Tretinoin" title="Tretinoin">Tretinoin</a><sup>#</sup>)</li> <li><a href="/wiki/Selinexor" title="Selinexor">Selinexor</a></li> <li><a href="/w/index.php?title=Sitimagene_ceradenovec&action=edit&redlink=1" class="new" title="Sitimagene ceradenovec (page does not exist)">Sitimagene ceradenovec</a></li> <li><a href="/wiki/Sotorasib" title="Sotorasib">Sotorasib</a></li> <li><a href="/wiki/Tagraxofusp" title="Tagraxofusp">Tagraxofusp</a></li> <li><a href="/wiki/Talimogene_laherparepvec" title="Talimogene laherparepvec">Talimogene laherparepvec</a></li> <li><a href="/wiki/Tazemetostat" title="Tazemetostat">Tazemetostat</a></li> <li><a href="/wiki/Tebentafusp" title="Tebentafusp">Tebentafusp</a></li> <li><a href="/wiki/Tiazofurine" class="mw-redirect" title="Tiazofurine">Tiazofurine</a></li> <li><a href="/wiki/Tigilanol_tiglate" title="Tigilanol tiglate">Tigilanol tiglate</a></li> <li><a href="/wiki/Tisagenlecleucel" title="Tisagenlecleucel">Tisagenlecleucel</a></li> <li><a href="/wiki/Trabectedin" title="Trabectedin">Trabectedin</a></li> <li><a href="/wiki/Veliparib" title="Veliparib">Veliparib</a></li> <li><a href="/wiki/Venetoclax" title="Venetoclax">Venetoclax</a></li> <li><a href="/w/index.php?title=Verdinexor&action=edit&redlink=1" class="new" title="Verdinexor (page does not exist)">Verdinexor</a></li> <li><a href="/wiki/Vosaroxin" title="Vosaroxin">Vosaroxin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="background: transparent; padding: 0px;"><div><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1&useformat=desktop" 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=Camptothecin&oldid=1226252715">https://en.wikipedia.org/w/index.php?title=Camptothecin&oldid=1226252715</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:Drugs_not_assigned_an_ATC_code" title="Category:Drugs not assigned an ATC code">Drugs not assigned an 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