{"id":1950,"date":"2022-08-25T19:18:34","date_gmt":"2022-08-25T13:48:34","guid":{"rendered":"https:\/\/chiralpedia.com\/blog\/?p=1950"},"modified":"2024-07-05T10:49:22","modified_gmt":"2024-07-05T05:19:22","slug":"terodiline","status":"publish","type":"post","link":"https:\/\/chiralpedia.com\/blog\/terodiline\/","title":{"rendered":"Terodiline"},"content":{"rendered":"\n

<\/p>\n\n\n\n

(\u00b1)-Terodiline, the antianginal agent, perhaps represents the best authenticated example of a drug that had to be withdrawn from the world market as consequence of proven stereospecific toxicity. Terodiline has a close similarity to prenylamine from a structural and pharmacological view point.<\/p>\n\n\n\n

\"\"<\/figure>\n\n\n\n

It was firs marketed as an antianginal agent but it exhibited urinary retention as a frequent and worrying side-effect. It was decided to exploit the the side-effect. Therefore the drug was redeveloped and marketed in 1986 for clinical use in urinary incontinence (leaking urine by accident<\/em>). Over a couple of years reports of serious cardiac toxicity started emerging following the clinical use of terodiline and some of them had a critical outcome. Because of these observations, in 1991, terodiline was withdrawn from the market world-wide<\/p>\n\n\n\n

Chirality and drug withdrawals<\/strong><\/p>\n\n\n\n

Terodiline has one stereogenic center and exists as mirror-image twins. Terodiline being structurally related to prenylamine demonstrates enantioselective pharmacological effects.  The calcium agonist activity remains predominantly in the (S<\/em>)-(-)-terodiline, whereas the anticholinergic actions is found in the (R<\/em>)-(+)-enantiomer. Both the pharmacodynamic actions possibly contribute to the overall therapeutic effect to a variable extent. <\/p>\n\n\n\n

\"\"
Terodiline – chiral twins<\/strong><\/figcaption><\/figure>\n\n\n\n

Enantioselective studies has shown that the (R )-(+)-terodiline is responsible for the prolongation of the QT interval associated with the racemic terodiline. Hence, the (R)-enantiomer is found to be the culprit for the serious ventricular tachyarrhythmias observed with the clinical use of this drug.<\/p>\n\n\n\n

Nomenclature<\/strong><\/p>\n\n\n\n

(RS<\/em>)-N-tert-butyl-4,4-diphenylbutan-2-amine (RS<\/em>)-N-tert-Butyl-1-methyl-3,3-diphenylpropylamine<\/p>\n\n\n\n

Therapeutic category<\/strong><\/p>\n\n\n\n

Antianginal and treat urinary incontinence – Withdrawn from world market due to stereospecific toxicity<\/strong><\/p>\n\n\n\n

Exercise<\/strong><\/p>\n\n\n\n

Learn to draw stereochemical structure, understand stereo-descriptors employed in the nomenclature system<\/p>\n\n\n\n

References<\/strong><\/p>\n\n\n\n

https:\/\/pubchem.ncbi.nlm.nih.gov\/compound\/Terodiline<\/a><\/p>\n\n\n\n

Eichelbaum, Michel F., Testa, Bernard, Somogyi, Andrew (Eds.). Stereochemical aspects of drug action and disposition, Springer, Page 401-32, 2003.<\/p>\n","protected":false},"excerpt":{"rendered":"

(\u00b1)-Terodiline, the antianginal agent, perhaps represents the best authenticated example of a drug that had to be withdrawn from the world market as consequence of proven stereospecific toxicity. Terodiline has a close similarity to prenylamine from a structural and pharmacological view point. It was firs marketed as an antianginal agent but it exhibited urinary retention as a frequent and worrying side-effect. It was decided to exploit the the side-effect. Therefore the drug was redeveloped and …<\/p>\n

Terodiline<\/span> Read More »<\/a><\/p>\n","protected":false},"author":1,"featured_media":2011,"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":[23,22,67,82],"ppma_author":[93],"class_list":["post-1950","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-chirality","tag-chiral_drugs","tag-chirality","tag-chiralpedia","tag-drug_withdrawls"],"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\/1950","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=1950"}],"version-history":[{"count":24,"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/posts\/1950\/revisions"}],"predecessor-version":[{"id":2403,"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/posts\/1950\/revisions\/2403"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/media\/2011"}],"wp:attachment":[{"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/media?parent=1950"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/categories?post=1950"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/tags?post=1950"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/chiralpedia.com\/blog\/wp-json\/wp\/v2\/ppma_author?post=1950"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}