{"id":1599,"date":"2022-08-08T13:43:00","date_gmt":"2022-08-08T08:13:00","guid":{"rendered":"https:\/\/chiralpedia.com\/blog\/?p=1599"},"modified":"2024-07-05T10:49:24","modified_gmt":"2024-07-05T05:19:24","slug":"levobupivacaine","status":"publish","type":"post","link":"https:\/\/chiralpedia.com\/blog\/levobupivacaine\/","title":{"rendered":"Levobupivacaine"},"content":{"rendered":"\n<p><\/p>\n\n\n\n<p>Bupivacaine is a long acting local anesthetic in use for many years as a spinal\/epidural anesthetic for childbirth and orthopedic procedures, such as hip replacement. It is marketed by AstraZeneca under the trade name&nbsp;Chirocaine. It acts by blocking Na+ channels and also has actions on the heart, which restrict its use by intravenous injection for regional anesthesia.<\/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 alignright size-full\"><img loading=\"lazy\" decoding=\"async\" width=\"224\" height=\"274\" src=\"https:\/\/chiralpedia.com\/blog\/wp-content\/uploads\/2022\/07\/LEVOBUPIVACAINE-1.png\" alt=\"\" class=\"wp-image-1615\"\/><figcaption>(S)-(-)-enantiomer of bupivacaine<\/figcaption><\/figure>\n\n\n\n<p>Bupivacaine is a racemic drug. This an example where the distomer shows toxic effect and the need for a switch. The chiral switch of (\u00b1)-bupivacaine, , (<em>S<\/em>)-(\u2013)-enantiomer levobupivacaine, has been developed successfully as a safer local anaesthetic that has the same therapeutic indications as the racemate. Levobupivacaine exhibits less vasodilation and possesses a greater length of action in comparison to&nbsp;bupivacaine. R-Bupivacaine, the distomer, has a greater risk of cardiotoxicity.<\/p>\n\n\n\n<p><strong>Claims justifying the switch<\/strong><\/p>\n\n\n\n<ul class=\"wp-block-list\"><li>Levobupivacaine has decreased risk of cardiotoxicity than the R-form and the racemate<\/li><li>Other clinical profiles are essentially similar as the racemate.<\/li><\/ul>\n\n\n\n<p><\/p>\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>(2<em>S<\/em>)-1-butyl-<em>N<\/em>-(2,6-dimethylphenyl)piperidine-2-carboxamide<\/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<p>Number levobupivacaine heterocyclic ring system. Understand the sterostructure. Look for alternate systematic names.<\/p>\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>Chiral switch. Wikipedia, Wikipedia Foundation, 080\/08\/2022. &nbsp;<a href=\"https:\/\/en.wikipedia.org\/wiki\/Chiral_switch\">https:\/\/en.wikipedia.org\/wiki\/Chiral_switch<\/a> and references therein<\/p>\n\n\n\n<p>Israel Agranat, Hava Caner and John Caldwell, Nature reviews, Drug Discovery, 1, October,| 753-768, 2002.<\/p>\n\n\n\n<p><a href=\"https:\/\/pubchem.ncbi.nlm.nih.gov\/compound\/Levobupivacaine\">https:\/\/pubchem.ncbi.nlm.nih.gov\/compound\/Levobupivacaine<\/a><\/p>\n","protected":false},"excerpt":{"rendered":"<p>Bupivacaine is a long acting local anesthetic in use for many years as a spinal\/epidural anesthetic for childbirth and orthopedic procedures, such as hip replacement. It is marketed by AstraZeneca under the trade name&nbsp;Chirocaine. It acts by blocking Na+ channels and also has actions on the heart, which restrict its use by intravenous injection for regional anesthesia. Chirality and Biological activity Bupivacaine is a racemic drug. This an example where the distomer shows toxic effect &hellip;<\/p>\n<p class=\"read-more\"> <a class=\"\" href=\"https:\/\/chiralpedia.com\/blog\/levobupivacaine\/\"> <span class=\"screen-reader-text\">Levobupivacaine<\/span> Read More &raquo;<\/a><\/p>\n","protected":false},"author":1,"featured_media":1609,"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-1599","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\/1599","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=1599"}],"version-history":[{"count":18,"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/posts\/1599\/revisions"}],"predecessor-version":[{"id":1702,"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/posts\/1599\/revisions\/1702"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/media\/1609"}],"wp:attachment":[{"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/media?parent=1599"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/categories?post=1599"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/tags?post=1599"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/ppma_author?post=1599"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}