Fluoxetine

Fluoxetine
(R)-fluoxetine (left), (S)-fluoxetine (right)
Clinical data
PronunciationUS: /fluˈɑːksətn/ floo-AHKS-ə-teen
UK: /fluˈɒksətn/ floo-OKS-ə-teen
Trade namesProzac, Sarafem, others
AHFS/Drugs.comMonograph
MedlinePlusa689006
License data
Pregnancy
category
  • AU: C
Addiction
liability
None
Routes of
administration
By mouth
Drug classSelective serotonin reuptake inhibitor (SSRI)
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability60–80%
Protein binding94–95%
MetabolismLiver (mostly CYP2D6-mediated)
MetabolitesNorfluoxetine, desmethylfluoxetine
Elimination half-life1–3 days (acute)
4–6 days (chronic)
ExcretionUrine (80%), feces (15%)
Identifiers
  • N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.125.370
Chemical and physical data
FormulaC17H18F3NO
Molar mass309.332 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
Melting point179 to 182 °C (354 to 360 °F)
Boiling point395 °C (743 °F)
Solubility in water14
  • CNCCC(c1ccccc1)Oc2ccc(cc2)C(F)(F)F
  • 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 Y
  • Key:RTHCYVBBDHJXIQ-UHFFFAOYSA-N Y
  (verify)

Fluoxetine, sold under the brand name Prozac, among others, is an antidepressant medication of the selective serotonin reuptake inhibitor (SSRI) class used for the treatment of major depressive disorder, anxiety, obsessive–compulsive disorder (OCD), panic disorder, premenstrual dysphoric disorder, and bulimia nervosa. It is also approved for treatment of major depressive disorder in adolescents and children 8 years of age and over. It has also been used to treat premature ejaculation. Fluoxetine is taken by mouth.

Common side effects include loss of appetite, nausea, diarrhea, headache, trouble sleeping, dry mouth, and sexual dysfunction. Serious side effects include serotonin syndrome, mania, seizures, an increased risk of suicidal behavior in people under 25 years old, and an increased risk of bleeding. Antidepressant discontinuation syndrome is less likely to occur with fluoxetine than with other antidepressants. Fluoxetine taken during pregnancy is associated with a significant increase in congenital heart defects in newborns. It has been suggested that fluoxetine therapy may be continued during breastfeeding if it was used during pregnancy or if other antidepressants were ineffective.

Fluoxetine was invented by Eli Lilly and Company in 1972 and entered medical use in 1986. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication. In 2022, it was the 22nd most commonly prescribed medication in the United States, with more than 24 million prescriptions.

Eli Lilly also markets fluoxetine in a fixed-dose combination with olanzapine as olanzapine/fluoxetine (Symbyax), which was approved by the US Food and Drug Administration (FDA) for the treatment of depressive episodes of bipolar I disorder in 2003 and for treatment-resistant depression in 2009.