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Fluoxetine_racemate
Fluoxetine racemate
Synonyms LY-110140
Brand names Lovan, Prozac and others
IUPAC name

IUPAC name
methyl({3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl})amine
ChemSpider

3269

DrugBank

DB00472

PubChem

3386

PDB fields

N/A

Formula

C17H18F3NO

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
InChIKey
InChIKey
RTHCYVBBDHJXIQ-UHFFFAOYSA-N
SMILES
SMILES
CNCCC(OC1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C1
(Jmol 3D structure)
Mol. mass

309.3261 g/mol

Fluoxetine is a selective serotonin reuptake inhibitor, that was the first such agent to be approved in the United States. It is also the agent with the longest half-life, along with its active metabolite norfluoxetine. In fact, a preparation called Prozac Weekly is available in the U.S., as it can be taken once a week. Consequently it is one of only two antidepressants (the other being agomelatine) that can be discontinued without any withdrawal syndrome being seen. It is also a potent inhibitor of CYP2D6, hence can interact with a wide variety of different agents including codeine, oxycodone, tamoxifen, aripiprazole and risperidone. It is considered the most stimulating (that is, most prone to wake people up, causing anxiety, insomnia, etc.) SSRI.[1] Likewise it also inhibits CYP2C19 and CYP3A4; induces CYP2C9.[1]

Other structural images[]

Fluoxetine structures
Fluoxetine racemate
(R)-fluoxetine
(S)-fluoxetine
350px (R)-fluoxetine
350px (S)-fluoxetine


External links[]

Reference list[]

  1. 1.0 1.1 Brunton, L; Chabner, B; Knollman, B (2010). Goodman and Gilman's The Pharmacological Basis of Therapeutics (12th ed.). New York, USA: McGraw-Hill Professional. ISBN 978-0-07-162442-8. 
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