{"id":1334,"date":"2022-07-25T08:05:00","date_gmt":"2022-07-25T02:35:00","guid":{"rendered":"https:\/\/chiralpedia.com\/blog\/?p=1334"},"modified":"2024-07-05T10:49:26","modified_gmt":"2024-07-05T05:19:26","slug":"levofloxacin","status":"publish","type":"post","link":"https:\/\/chiralpedia.com\/blog\/levofloxacin\/","title":{"rendered":"Levofloxacin"},"content":{"rendered":"\n<p><\/p>\n\n\n\n<p>Levofloxacin is a third generation fluoroquinolone that is widely used in the treatment of mild-to-moderate respiratory and urinary tract infections due to sensitive organisms.&nbsp; Levofloxacin is an antibacterial prescription medicine approved by the U.S. Food and Drug Administration (FDA) for the treatment of certain bacterial infections, such as community-acquired pneumonia, acute worsening of chronic bronchitis, anthrax, urinary tract infections, acute sinus infections, and others.<\/p>\n\n\n\n<p class=\"has-ast-global-color-0-color has-text-color has-medium-font-size\"><strong>Chirality and biological activity<\/strong><\/p>\n\n\n\n<figure class=\"wp-block-image aligncenter size-full is-resized\"><img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/chiralpedia.com\/blog\/wp-content\/uploads\/2022\/07\/LEVOFLOXACIN.png\" alt=\"\" class=\"wp-image-1341\" width=\"333\" height=\"204\" srcset=\"https:\/\/chiralpedia.com\/blog\/wp-content\/uploads\/2022\/07\/LEVOFLOXACIN.png 394w, https:\/\/chiralpedia.com\/blog\/wp-content\/uploads\/2022\/07\/LEVOFLOXACIN-300x184.png 300w\" sizes=\"auto, (max-width: 333px) 100vw, 333px\" \/><figcaption><strong>Levofloxacin<\/strong><\/figcaption><\/figure>\n\n\n\n<p>Levofloxacin, the S-enantiomer of the previously marketed racemic antibacterial (\u00b1)-Ofloxacin. This is referred to as a chiral switch. (Read more @ my page in Wikipedia &#8211;  &lt;Chiral switch. Wikipedia, Wikipedia Foundation, 25\/07\/2022. &nbsp;<a href=\"https:\/\/en.wikipedia.org\/wiki\/Chiral_switch\">https:\/\/en.wikipedia.org\/wiki\/Chiral_switch<\/a>&gt;.) Ofloxacin carries one stereogenic center in the 1,4- oxazine, a heterocyclic ring system, of the molecule and exist as pair of enantiomers. The (S)-version, Levofloxacin, has the desired antibacterial activity and called the eutomer. The (R)-form is pharmacologically inactive and referred to as the distomer. To know more about eutomer and distomer nomenclature read @ &lt;<a href=\"https:\/\/chiralpedia.com\/blog\/chiral-twins-identical-but-not-really\">https:\/\/chiralpedia.com\/blog\/chiral-twins-identical-but-not-really<\/a>\/&gt;<\/p>\n\n\n\n<p>The reason for the development of a single-enantiomer of racemic Ofloxacin is that:<\/p>\n\n\n\n<ul class=\"wp-block-list\"><li>(S)-isomer, Levofloxacin is 8-125 fold greater antibacterial potency. <\/li><li>Higher water solubility than the R-isomer. <\/li><li>Also enantiomeric disposition favor single-enantiomer.<\/li><\/ul>\n\n\n\n<p class=\"has-ast-global-color-0-color has-text-color has-medium-font-size\"><strong>Nomenclature<\/strong><\/p>\n\n\n\n<p>(S)-9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7<em>H<\/em>-pyrido[1,2,3-<em>de<\/em>][1,4]benzoxazine-6-carboxylic acid<\/p>\n\n\n\n<p class=\"has-ast-global-color-0-color has-text-color has-medium-font-size\"><strong>Therapeutic category<\/strong><\/p>\n\n\n\n<p>Anti-bacterial<\/p>\n\n\n\n<p class=\"has-ast-global-color-0-color has-text-color has-medium-font-size\"><strong>Exercise<\/strong><\/p>\n\n\n\n<ol class=\"wp-block-list\"><li>Number the Levofloxacin heterocyclic ring and understand the nomenclature<\/li><li>Draw the stereochemical structure of the mirror-image twin of Levofloxacin<\/li><\/ol>\n\n\n\n<p class=\"has-ast-global-color-0-color has-text-color has-medium-font-size\"><strong>References<\/strong><\/p>\n\n\n\n<p>Joseph Gal in&nbsp;<strong><em>Chirality in drug research<\/em><\/strong>. Edited by Eric Francotte, W. Lindner. Weinheim: Wiley-VCH.&nbsp;ISBN&nbsp;978-3-527-60943-7.&nbsp;Page 3-25, 2006.<\/p>\n\n\n\n<p>Stereochemical Aspects of Drug Action and Disposition,Editors: Eichelbaum, Michel F., Testa, Bernard, Somogyi, Andrew (Eds.) Springer, 2003. <a rel=\"noreferrer noopener\" href=\"https:\/\/www.springer.com\/gp\/book\/9783642625756\" target=\"_blank\">https:\/\/www.springer.com\/gp\/book\/9783642625756<\/a><\/p>\n\n\n\n<h3 class=\"has-small-font-size wp-block-heading\">                                                 Wainer, l. W., &amp; Drayer, D. E., Eds.&nbsp;<em><strong>Drug stereochemistry and Pharmacology<\/strong><\/em>: Marcel-Dekker, New York,1988.<\/h3>\n\n\n\n<p>Chiral drug. Wikipedia, Wikipedia Foundation, 25\/07\/2022. <a href=\"https:\/\/en.wikipedia.org\/wiki\/Chiral_drugs\">https:\/\/en.wikipedia.org\/wiki\/Chiral_drugs<\/a><\/p>\n\n\n\n<p>Chiral switch. Wikipedia, Wikipedia Foundation, 25\/07\/2022. &nbsp;<a href=\"https:\/\/en.wikipedia.org\/wiki\/Chiral_switch\">https:\/\/en.wikipedia.org\/wiki\/Chiral_switch<\/a><\/p>\n\n\n\n<p>Harkishan Singh and V.K. Kapoor.<em><strong>&nbsp;Medicinal chemistry and pharmaceutical chemistry<\/strong>,<\/em>&nbsp;Vallabh Prakashan, New Delhi, Page 603-06, 2012.<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Levofloxacin is a third generation fluoroquinolone that is widely used in the treatment of mild-to-moderate respiratory and urinary tract infections due to sensitive organisms.&nbsp; Levofloxacin is an antibacterial prescription medicine approved by the U.S. Food and Drug Administration (FDA) for the treatment of certain bacterial infections, such as community-acquired pneumonia, acute worsening of chronic bronchitis, anthrax, urinary tract infections, acute sinus infections, and others. Chirality and biological activity Levofloxacin, the S-enantiomer of the previously marketed &hellip;<\/p>\n<p class=\"read-more\"> <a class=\"\" href=\"https:\/\/chiralpedia.com\/blog\/levofloxacin\/\"> <span class=\"screen-reader-text\">Levofloxacin<\/span> Read More &raquo;<\/a><\/p>\n","protected":false},"author":1,"featured_media":1336,"comment_status":"open","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"_monsterinsights_skip_tracking":false,"_monsterinsights_sitenote_active":false,"_monsterinsights_sitenote_note":"","_monsterinsights_sitenote_category":0,"site-sidebar-layout":"","site-content-layout":"","ast-main-header-display":"","ast-hfb-above-header-display":"","ast-hfb-below-header-display":"","ast-hfb-mobile-header-display":"","site-post-title":"","ast-breadcrumbs-content":"","ast-featured-img":"","footer-sml-layout":"","theme-transparent-header-meta":"","adv-header-id-meta":"","stick-header-meta":"","header-above-stick-meta":"","header-main-stick-meta":"","header-below-stick-meta":"","footnotes":""},"categories":[43],"tags":[23,22,67,65],"ppma_author":[93],"class_list":["post-1334","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-chirality","tag-chiral_drugs","tag-chirality","tag-chiralpedia","tag-cmotw"],"authors":[{"term_id":93,"user_id":1,"is_guest":0,"slug":"chiralusrblg","display_name":"Valliappan Kannappan","avatar_url":{"url":"https:\/\/chiralpedia.com\/blog\/wp-content\/uploads\/2024\/09\/vk.jpg","url2x":"https:\/\/chiralpedia.com\/blog\/wp-content\/uploads\/2024\/09\/vk.jpg"},"first_name":"","last_name":"","user_url":"https:\/\/chiralpedia.com\/blog\/","job_title":"Founder, chiralpedia.com","description":""}],"_links":{"self":[{"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/posts\/1334","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/comments?post=1334"}],"version-history":[{"count":31,"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/posts\/1334\/revisions"}],"predecessor-version":[{"id":2270,"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/posts\/1334\/revisions\/2270"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/media\/1336"}],"wp:attachment":[{"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/media?parent=1334"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/categories?post=1334"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/tags?post=1334"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/ppma_author?post=1334"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}