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| Formula | C20H25NO |
| Molar mass | 295.426 g·mol−1 |
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Talopram (Lu 3-010),[1] also known asphthalapromine, is aselectivenorepinephrine reuptake inhibitor (NRI) which was researched for the management ofdepression in the 1960s and 1970s but was never commercialized. Along withtalsupram, talopram isstructurally related to theselective serotonin reuptake inhibitor (SSRI)citalopram,[2] as well as tomelitracen:[3]
In 1971, the company hiredKlaus Bøgesø as a medicinal chemist. Over the years Bøgesø turned out to have aMidas touch at the game of drug hunting, creating more molecules that made it to the market than almost any other medicinal chemist in the field. The challenge facing him in 1971 following his recruitment was to produce a selective norepinephrine reuptake inhibitor. Like other companies at the time,Lundbeck had little interest in an SSRI. Bøgesø began from an accident in the laboratory. Trying to create a derivative of their norepinephrine reuptake inhibiting antidepressant melitracen, Lundbeck chemists accidentally produced a new chemical — a phenylphthalene. Against all the odds, just likemelitracen, this was also a selective norepinephrine reuptake inhibitor. Two potential antidepressants came out of this — talopram and tasulopram, which were pressed into clinical trials. Both however turned out to be energizing, and in a number of cases there were suicide attempts. The fact that there were suicide attempts appeared to confirm another proposal ofPaul Kielholz, that activating antidepressants might lead to suicide. Lundbeck's experience suggested that norepinephrine reuptake inhibitors were likely to lead to just this problem. Lundbeck retreated, scared. If norepinephrine reuptake inhibitors were likely to trigger suicide, the greatest hazard of an antidepressant, then Kielholz's view suggested that an SSRI would be less likely to lead to suicide. Bøgesø's job was to see whether the new series of drugs could be converted into a series of SSRIs. Following a lead from Carlsson on how to do this, he converted talopram into citalopram, the most selective serotonin reuptake inhibitor to come to the market.
An unexpected/fortuitous rearrangement product in the synthesis oflitracen is what led to talopram.[3][4]
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