Fluoxetine

Chemistry

Also known as

• 54910-89-3
• Fluoxetina
• Fluval
• N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine
• Animex-On
• Fluoxetinum
• Fluoxetin
• Fluoxetin ratiopharm

Stereoisomers

2 distinct stereoisomers are registered for this structure. This area's record is the racemate — the mixture, which is normally the form encountered.

• Fluoxetine this area mixture CID 3386
• (S)-Fluoxetine CID 1548968
• (+)-Fluoxetine CID 1548970

Prescribed as the racemate. Both enantiomers inhibit serotonin reuptake with broadly similar potency, so unlike escitalopram there is no single-enantiomer version worth marketing. They differ downstream: S-norfluoxetine, the metabolite, is the long-lived active one and is why fluoxetine takes weeks to clear.

Attribution

• Bryan Molloy — first synthesis, 1972

  With Klaus Schmiegel, from a project begun with Ray Fuller in 1970.

• David T. Wong — discovered its activity, 1974

  Identified it as the series' most serotonin-selective member.