Fluoxetine

"Prozac" redirects here. For other uses, see Prozac (disambiguation).
Not to be confused with Fluvoxamine.

Fluoxetine
Fluoxetine (top),
(R)-fluoxetine (left), (S)-fluoxetine (right)
Clinical data
Pronunciation/fluˈɒksətiːn/
floo-OKS-ə-teen
Trade namesProzac, Sarafem, others
AHFS/Drugs.comMonograph
MedlinePlusa689006
License data
Pregnancy
category
  • AU: C
Addiction
liability		None[1]
Routes of
administration		By mouth
Drug classSelective serotonin reuptake inhibitor (SSRI)[2]
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability60–80%[2]
Protein binding94–95%[7]
MetabolismLiver (mostly CYP2D6-mediated)[9]
MetabolitesNorfluoxetine, desmethylfluoxetine
Elimination half-life1–3 days (acute)
4–6 days (chronic)[9][10]
ExcretionUrine (80%), faeces (15%)[9][10]
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 Edit this at Wikidata
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 checkY
  • Key:RTHCYVBBDHJXIQ-UHFFFAOYSA-N checkY
  (verify)

Fluoxetine, sold under the brand name Prozac, among others, is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class.[2] It is used for the treatment of major depressive disorder, obsessive–compulsive disorder (OCD), anxiety, bulimia nervosa, panic disorder, and premenstrual dysphoric disorder.[2] It is also approved for treatment of major depressive disorder in adolescents and children 8 years of age and over.[11] It has also been used to treat premature ejaculation.[2] Fluoxetine is taken by mouth.[2]

Common side effects include indigestion, trouble sleeping, sexual dysfunction, loss of appetite, nausea, diarrhea, dry mouth, and rash. 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.[2] Antidepressant discontinuation syndrome is less likely to occur with fluoxetine than with other antidepressants, but it still happens in many cases. Fluoxetine taken during pregnancy is associated with significant increase in congenital heart defects in the newborns.[12][13] It has been suggested that fluoxetine therapy may be continued during breastfeeding if it was used during pregnancy or if other antidepressants were ineffective.[14]

Fluoxetine was invented by Eli Lilly and Company in 1972, and entered medical use in 1986.[15] It is on the World Health Organization's List of Essential Medicines.[16] It is available as a generic medication.[2] In 2022, it was the 22nd most commonly prescribed medication in the United States, with more than 24 million prescriptions.[17][18]

Eli Lilly also markets fluoxetine in a fixed-dose combination with olanzapine as olanzapine/fluoxetine (Symbyax), which was approved by the U.S. FDA for the treatment of depressive episodes of bipolar I disorder in 2003 and for treatment-resistant depression in 2009.[19][20]

  1. ^ Hubbard JR, Martin PR (2001). Substance Abuse in the Mentally and Physically Disabled. CRC Press. p. 26. ISBN 978-0-8247-4497-7.
  2. ^ a b c d e f g h "Fluoxetine Hydrochloride". The American Society of Health-System Pharmacists. Archived from the original on 8 December 2015. Retrieved 2 December 2015.
  3. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  4. ^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
  5. ^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.
  6. ^ "Mental health". Health Canada. 9 May 2018. Retrieved 13 April 2024.
  7. ^ a b Cite error: The named reference Prozac FDA label was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference Sarafem FDA label was invoked but never defined (see the help page).
  9. ^ a b c "Prozac Fluoxetine Hydrochloride" (PDF). TGA eBusiness Services. Eli Lilly Australia Pty. Limited. 9 October 2013. Archived from the original on 25 April 2017. Retrieved 23 November 2013.
  10. ^ a b Altamura AC, Moro AR, Percudani M (March 1994). "Clinical pharmacokinetics of fluoxetine". Clinical Pharmacokinetics. 26 (3): 201–14. doi:10.2165/00003088-199426030-00004. PMID 8194283. S2CID 1406955.
  11. ^ "Depressive Disorders in Children and Adolescents – Pediatrics". Merck Manuals Professional Edition. Retrieved 25 December 2020.
  12. ^ Cite error: The named reference pmid30415641 was invoked but never defined (see the help page).
  13. ^ Cite error: The named reference pmid33354752 was invoked but never defined (see the help page).
  14. ^ "Fluoxetine Pregnancy and Breastfeeding Warnings". Archived from the original on 31 August 2017. Retrieved 2 December 2015.
  15. ^ Myers RL (2007). The 100 most important chemical compounds: a reference guide (1st ed.). Westport, CN: Greenwood Press. p. 128. ISBN 978-0-313-33758-1.
  16. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  17. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  18. ^ "Fluoxetine Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
  19. ^ "Symbyax- olanzapine and fluoxetine hydrochloride capsule". DailyMed. 21 April 2020. Retrieved 30 September 2020.
  20. ^ Grohol, J. "FDA Approves Symbyax for Treatment Resistant Depression". Psych Central Blog. Archived from the original on 26 December 2017. Retrieved 17 July 2010.