Trademarks: Prozac; Sarafem; Fontex
Molecular Formula: C17H18F3NO
CAS Registry Number: 54910-89-3
CAS Name: methyl({3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl})amine
Molecular Weight: 309.326
SMILES: COC1=C(OC)C=C2C(=O)C(CC3CCN(CC4=CC=CC=C4)CC3)CC2=C1
InChI Key: RTHCYVBBDHJXIQ-UHFFFAOYSA-N
InChI: InChI=1S/C17H18F3NO/c1-21-12-11-16(13-5-3-2-4-6-13)22-15-9-7-14(8-10-15)17(18,19)20/h2-10,16,21H,11-12H2,1H3
Activity: Selective Serotonin-Reuptake Inhibitors; SSRI Inhibitors; Major Depressive Disorder Therapy; Obsessive-Compulsive Disorder Therapy; OCD Therapy; Premenstrual Dysphoric Disorder Therapy; Serotonin Uptake Inhibitors; Serotonin Agents; Antidepressive Agents; Second Generation Antidepressive Agents
Status: Launched 1987
Originator: Eli Lily
Fluoxetine synthesis: US4314081A
Fluoxetine is marketed as a racemate. Both of its enantiomers display similar activity both in vitro (Ki, (R)-(+)-enantiomer is 21 nM and Ki, (S)-(-)- enantiomer is 33 nM) and in vivo. However, it is (S)-fluoxetine that is the predominant therapeutic enantiomer since it is eliminated more slowly that the (R)-enantiomer.
(S)-fluoxetine synthesis: J Med Chem 1988, 31(7), 1412-1417
References:
1. Molloy, B. B.; et. al. Antidepressants. US4314081A
2. Robertson, D. W.; et. al. The absolute configurations and pharmacological activities of the optical isomers of fluoxetine, a selective serotonin-uptake inhibitor. J Med Chem 1988, 31(7), 1412-1417.
3. Stokes, P. E. Fluoxetine: a five-year review. Clin Ther 1993, 15(2), 216-243. (activity)
4. Rossi, A.; et. al. Fluoxetine: a review on evidence based medicine. Ann Gen Hosp Psychiatry 2004, 3, 2. (activity)
