{"id":1395,"date":"2022-07-28T09:52:00","date_gmt":"2022-07-28T04:22:00","guid":{"rendered":"https:\/\/chiralpedia.com\/blog\/?p=1395"},"modified":"2024-07-05T10:49:26","modified_gmt":"2024-07-05T05:19:26","slug":"esomeprazole","status":"publish","type":"post","link":"https:\/\/chiralpedia.com\/blog\/esomeprazole\/","title":{"rendered":"Esomeprazole"},"content":{"rendered":"\n<p><\/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\/Esomeprazole_780\u00d7300_3D_Conformer.png\" alt=\"\" class=\"wp-image-1398\" width=\"378\" height=\"153\" srcset=\"https:\/\/chiralpedia.com\/blog\/wp-content\/uploads\/2022\/07\/Esomeprazole_780\u00d7300_3D_Conformer.png 599w, https:\/\/chiralpedia.com\/blog\/wp-content\/uploads\/2022\/07\/Esomeprazole_780\u00d7300_3D_Conformer-300x121.png 300w\" sizes=\"auto, (max-width: 378px) 100vw, 378px\" \/><\/figure>\n\n\n\n<p>Esomeprazole is&nbsp;used to treat conditions where there is too much acid in the stomach. It is used to treat duodenal and gastric ulcers, erosive esophagitis,&nbsp;gastroesophageal reflux disease (GERD), and Zollinger-Ellison syndrome, a condition wherein the stomach produces too much acid. It was launched by AstraZeneca, in 2000. Esomeprazole magnesium [AstraZeneca; <a href=\"http:\/\/www.astrazeneca.com\">http:\/\/www.astrazeneca.com<\/a>] (gastrointestinal). <\/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<p>Esomeprazole is the (S)-(\u2212)-enantiomer of (\u00b1)-omeprazole. It is a chiral switch (Read more about chiral switch @ my page in Wikipedia &#8211; &lt;Chiral switch. Wikipedia, Wikipedia Foundation, 22\/07\/2022. &nbsp;<a href=\"https:\/\/en.wikipedia.org\/wiki\/Chiral_switch\">https:\/\/en.wikipedia.org\/wiki\/Chiral_switch<\/a>&gt;.) Its chirality stems from the presence of stereogenic center at the sulfur atom of methylsulfinyl bridge between 1H-benzimidazole and the pyridine moieties. <\/p>\n\n\n\n<figure class=\"wp-block-image aligncenter size-full\"><img loading=\"lazy\" decoding=\"async\" width=\"399\" height=\"281\" src=\"https:\/\/chiralpedia.com\/blog\/wp-content\/uploads\/2022\/07\/Esomeprazole-3.png\" alt=\"\" class=\"wp-image-1551\" srcset=\"https:\/\/chiralpedia.com\/blog\/wp-content\/uploads\/2022\/07\/Esomeprazole-3.png 399w, https:\/\/chiralpedia.com\/blog\/wp-content\/uploads\/2022\/07\/Esomeprazole-3-300x211.png 300w\" sizes=\"auto, (max-width: 399px) 100vw, 399px\" \/><figcaption><strong>Esomeprazole<\/strong><\/figcaption><\/figure>\n\n\n\n<p>In commercial terms, probably the most important chiral switch so far has been the switch from the blockbuster gastric anti-secretory proton pump (H+\/K+-ATPase) inhibitor (PPI) omeprazole to esomeprazole. (\u00b1)-Omeprazole is a racemate launched in 1988 by Astra AB was the world\u2019s highest-selling drug, and had worldwide annual sales of US $6.2 billion in 2000.<\/p>\n\n\n\n<p class=\"has-ast-global-color-0-color has-text-color\"><strong>Claims for the switch from (\u00b1)-Omeprazole to S-Omeprazole include:<\/strong><\/p>\n\n\n\n<ul class=\"wp-block-list\"><li>Less variable metabolism; Esomeprazole&nbsp; clearance is less dependent on CYP2C19 than the racemate<\/li><li>Higher dose efficiency \u2013 S-isomer&nbsp; 4 x better in preventing acid &nbsp;&nbsp;&nbsp;&nbsp;secretion than R-isomer<\/li><li>Lower first pass metabolism<\/li><li>Slower plasma clearance and increased systemic availability compared to R- isomer;<\/li><li>Increased clinical efficiency<\/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>(S)-(-)-&nbsp;5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole                                                                     <\/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>Proton pump inhibitor; Treatment of peptic ulcer disease<\/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>Identify the stereogenic center in Esomeprazole <\/li><li>Number the ring system and examine the nomenclature <\/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>Israel Agranat, Hava Caner and John Caldwell, Nature reviews, Drug Discovery, 1, October,| 753-768, 2002.<\/p>\n\n\n\n<p>Hans-J\u00fcrgen Federsel in&nbsp;<em>Chirality in drug research.<\/em> Edited by Eric Francotte, W. Lindner. Weinheim: Wiley-VCH.&nbsp;ISBN&nbsp;978-3-527-60943-7.&nbsp;Page 39 2006.<\/p>\n\n\n\n<p>Chiral switch. Wikipedia, Wikipedia Foundation, 22\/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><\/p>\n","protected":false},"excerpt":{"rendered":"<p>Esomeprazole is&nbsp;used to treat conditions where there is too much acid in the stomach. It is used to treat duodenal and gastric ulcers, erosive esophagitis,&nbsp;gastroesophageal reflux disease (GERD), and Zollinger-Ellison syndrome, a condition wherein the stomach produces too much acid. It was launched by AstraZeneca, in 2000. Esomeprazole magnesium [AstraZeneca; http:\/\/www.astrazeneca.com] (gastrointestinal). Chirality and biological activity Esomeprazole is the (S)-(\u2212)-enantiomer of (\u00b1)-omeprazole. It is a chiral switch (Read more about chiral switch @ my page &hellip;<\/p>\n<p class=\"read-more\"> <a class=\"\" href=\"https:\/\/chiralpedia.com\/blog\/esomeprazole\/\"> <span class=\"screen-reader-text\">Esomeprazole<\/span> Read More &raquo;<\/a><\/p>\n","protected":false},"author":1,"featured_media":0,"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-1395","post","type-post","status-publish","format-standard","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\/1395","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=1395"}],"version-history":[{"count":38,"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/posts\/1395\/revisions"}],"predecessor-version":[{"id":2278,"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/posts\/1395\/revisions\/2278"}],"wp:attachment":[{"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/media?parent=1395"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/categories?post=1395"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/tags?post=1395"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/ppma_author?post=1395"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}