Seproxetine

Seproxetine

Seproxetine
Systematic (IUPAC) name
(S)-3-Phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine
Clinical data
Legal status
  • Uncontrolled
Routes Oral
Pharmacokinetic data
Half-life 4-16 days
Identifiers
CAS number
ATC code None
PubChem
IUPHAR ligand
DrugBank
ChemSpider
UNII  YesY
Chemical data
Formula C16H16F3NO 
Mol. mass 295.30 g/mol

Seproxetine, also known as (S)-norfluoxetine, is a selective serotonin reuptake inhibitor (SSRI). It is the most important active metabolite of the widely used antidepressant fluoxetine, but little is known about its pharmacological actions. Seproxetine was being investigated by Eli Lilly and Company as an antidepressant; however, a cardiac side effect was noted and development was discontinued.

Synthesis

Seproxetine can be synthesized from a protected 3-amino-1-phenylpropan-1-ol and 1-fluoro-4-trifluoromethyl(benzene):

Seproxetine synthesis: Fuller, R. W.; Robertson, D. W.; Wong, D. T.; European Patent, 1990, EP 0369685 

References