{"id":1525,"date":"2022-08-03T07:49:23","date_gmt":"2022-08-03T02:19:23","guid":{"rendered":"https:\/\/chiralpedia.com\/blog\/?p=1525"},"modified":"2024-07-05T10:49:25","modified_gmt":"2024-07-05T05:19:25","slug":"propoxyphene","status":"publish","type":"post","link":"https:\/\/chiralpedia.com\/blog\/propoxyphene\/","title":{"rendered":"Propoxyphene"},"content":{"rendered":"\n<p><\/p>\n\n\n\n<p class=\"has-ast-global-color-0-color has-text-color has-medium-font-size\"><strong>Chiral twins with independent therapeutic value<\/strong><\/p>\n\n\n\n<p>Propoxyphene is a classical example of a synthetic chiral drug where the<em> enantiomers of a chiral drug exhibit desirable but different therapeutic activity<\/em>. Example of such biological behavior is exemplified by some of the natural products as well (e.g., <em>quinine and quinidine<\/em>) with anti-malarial and anti-arrhythmic activity.<\/p>\n\n\n\n<figure class=\"wp-block-image aligncenter size-full\"><img loading=\"lazy\" decoding=\"async\" width=\"381\" height=\"300\" src=\"https:\/\/chiralpedia.com\/blog\/wp-content\/uploads\/2022\/07\/Dextropropoxyphene_780\u00d7300_3D_Conformer-4.png\" alt=\"\" class=\"wp-image-1632\" srcset=\"https:\/\/chiralpedia.com\/blog\/wp-content\/uploads\/2022\/07\/Dextropropoxyphene_780\u00d7300_3D_Conformer-4.png 381w, https:\/\/chiralpedia.com\/blog\/wp-content\/uploads\/2022\/07\/Dextropropoxyphene_780\u00d7300_3D_Conformer-4-300x236.png 300w\" sizes=\"auto, (max-width: 381px) 100vw, 381px\" \/><\/figure>\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>Propoxyphene carries two stereogenic centers meaning it can exist in two pair of enantiomers (4 stereoisomers). One of the enantiomeric pairs the (+)-Dexpropoxyphene is analgesic where as the (-)-Levopropoxyphene is effective antitussive but has no analgesic activity.<\/p>\n\n\n\n<figure class=\"wp-block-image aligncenter size-full\"><img loading=\"lazy\" decoding=\"async\" width=\"662\" height=\"396\" src=\"https:\/\/chiralpedia.com\/blog\/wp-content\/uploads\/2022\/08\/Propoxyphene.png\" alt=\"\" class=\"wp-image-1691\" srcset=\"https:\/\/chiralpedia.com\/blog\/wp-content\/uploads\/2022\/08\/Propoxyphene.png 662w, https:\/\/chiralpedia.com\/blog\/wp-content\/uploads\/2022\/08\/Propoxyphene-300x179.png 300w\" sizes=\"auto, (max-width: 662px) 100vw, 662px\" \/><\/figure>\n\n\n\n<p>Interesting to note that the mirror-image relationship is reflected in the trade names (DARVON and NOVRAD) under which the drugs are marketed by Eli Lilly.<\/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>Dexpropoxyphene:  [(2<em>S<\/em>,3<em>R<\/em>)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate  <\/p>\n\n\n\n<p>Levopropoxyphene: [(2<em>R<\/em>,3<em>S<\/em>)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate<\/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>Understand the nomenclature and stereo-descriptors employed in describing the enantiomeric pair of propoxyphene<\/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 drug. Wikipedia, Wikipedia Foundation, 03\/08\/2022. &nbsp;<a href=\"https:\/\/en.wikipedia.org\/wiki\/Chiral_drugs\">https:\/\/en.wikipedia.org\/wiki\/Chiral_drugs<\/a> and references therein<\/p>\n\n\n\n<p><a href=\"https:\/\/pubchem.ncbi.nlm.nih.gov\/compound\/dextropropoxyphene#section=Names-and-Identifiers\">https:\/\/pubchem.ncbi.nlm.nih.gov\/compound\/dextropropoxyphene#section=Names-and-Identifiers<\/a><\/p>\n\n\n\n<p><a href=\"https:\/\/pubchem.ncbi.nlm.nih.gov\/compound\/levopropoxyphene#section=Names-and-Identifiers\">https:\/\/pubchem.ncbi.nlm.nih.gov\/compound\/levopropoxyphene#section=Names-and-Identifiers<\/a><\/p>\n","protected":false},"excerpt":{"rendered":"<p>Chiral twins with independent therapeutic value Propoxyphene is a classical example of a synthetic chiral drug where the enantiomers of a chiral drug exhibit desirable but different therapeutic activity. Example of such biological behavior is exemplified by some of the natural products as well (e.g., quinine and quinidine) with anti-malarial and anti-arrhythmic activity. Chirality and biological activity Propoxyphene carries two stereogenic centers meaning it can exist in two pair of enantiomers (4 stereoisomers). One of &hellip;<\/p>\n<p class=\"read-more\"> <a class=\"\" href=\"https:\/\/chiralpedia.com\/blog\/propoxyphene\/\"> <span class=\"screen-reader-text\">Propoxyphene<\/span> Read More &raquo;<\/a><\/p>\n","protected":false},"author":1,"featured_media":1693,"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-1525","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\/1525","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=1525"}],"version-history":[{"count":21,"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/posts\/1525\/revisions"}],"predecessor-version":[{"id":1694,"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/posts\/1525\/revisions\/1694"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/media\/1693"}],"wp:attachment":[{"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/media?parent=1525"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/categories?post=1525"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/tags?post=1525"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/ppma_author?post=1525"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}