{"id":1705,"date":"2022-08-10T07:27:00","date_gmt":"2022-08-10T01:57:00","guid":{"rendered":"https:\/\/chiralpedia.com\/blog\/?p=1705"},"modified":"2024-07-05T10:49:24","modified_gmt":"2024-07-05T05:19:24","slug":"citalopram","status":"publish","type":"post","link":"https:\/\/chiralpedia.com\/blog\/citalopram\/","title":{"rendered":"Escitalopram"},"content":{"rendered":"\n

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

Citalopram belongs to a class of antidepressant agents known as selective serotonin-reuptake inhibitors (SSRIs). It is indicated for the treatment of depression.<\/p>\n\n\n\n

\"\"
Escitalopram<\/strong><\/figcaption><\/figure>\n\n\n\n

Chirality and biological activity<\/strong><\/p>\n\n\n\n

Citalopram has one stereocenter, to which a 4-fluoro phenyl group and an N, N-dimethyl-3-aminopropyl group are linked. As a consequence the molecule exists as an enantiomeric pair, the S-(+)-citalopram and R-(\u2013)-citalopram.<\/p>\n\n\n\n

The selective serotonin-reuptake inhibitor  activity resides primarily in the  S-enantiomer (eutomer) while the R-enantiomer is 30-fold less potent (distomer). To know more about eutomer and distomer nomenclature read @ <https:\/\/chiralpedia.com\/blog\/chiral-twins-identical-but-not-really<\/a>\/> In clinical trials, both racemic (R,S)-citalopram and (S)-citalopram were significantly better than placebo for improving depression and data suggests that (S)-citalopram has greater efficacy than and fewer side-effects than the (\u00b1)-citalopram. By and large, (S)-citalopram appears to have advantages over (\u00b1)-citalopram and is a good example of the potential benefits of enantiopure drugs.<\/p>\n\n\n\n

Reasoning for the chiral switch<\/strong><\/p>\n\n\n\n