User:Mr. Ibrahem/Fluoxetine

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Not to be confused with Fluvoxamine.


Mr. Ibrahem/Fluoxetine
Fluoxetine (top),
(R)-fluoxetine (left), (S)-fluoxetine (right)
Clinical data
Pronunciation/fluˈɒksətiːn/
Trade namesProzac, Sarafem, Adofen, other
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]
Legal status
Legal status
Pharmacokinetic data
Bioavailability60–80%[2]
Protein binding94–95%[3]
MetabolismLiver (mostly CYP2D6-mediated)[5]
Metabolitesnorfluoxetine, desmethylfluoxetine
Onset of action2 to 3 weeks[4]
Elimination half-life1–3 days (acute)
4–6 days (chronic)[5][6]
ExcretionUrine (80%), faeces (15%)[5][6]
Identifiers
  • N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine
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 mg/mL (20 °C)
  • 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 names Prozac and Sarafem 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), bulimia nervosa, panic disorder, and premenstrual dysphoric disorder.[2] It may decrease the risk of suicide in those over the age of 65.[2] 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, dry mouth, rash, and abnormal dreams.[2] 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] If stopped suddenly, a withdrawal syndrome may occur with anxiety, dizziness, and changes in sensation.[2] It is unclear if it is safe in pregnancy.[8] If already on the medication, it may be reasonable to continue during breastfeeding.[8] Its mechanism of action is not entirely clear but believed to be related to increasing serotonin activity in the brain.[2]

Fluoxetine was discovered by Eli Lilly and Company in 1972, and entered medical use in 1986.[9] It is on the World Health Organization's List of Essential Medicines.[10] It is available as a generic medication.[2] The wholesale cost in the developing world is between US$0.01 and US$0.04 per day as of 2014.[11] In the United States, it costs about US$0.85 per day.[2] In 2017, it was the 31st most commonly prescribed medication in the United States, with more than 21 million prescriptions.[12][13]

References[edit]

  1. ^ Hubbard, John R.; Martin, Peter R. (2001). Substance Abuse in the Mentally and Physically Disabled. CRC Press. p. 26. ISBN 9780824744977. Archived from the original on 1 August 2020. Retrieved 3 August 2020.
  2. ^ a b c d e f g h i j k l m "Fluoxetine Hydrochloride". The American Society of Health-System Pharmacists. Archived from the original on 8 December 2015. Retrieved 2 December 2015.
  3. ^ "Prozac Label" (PDF). FDA. 2014. Archived (PDF) from the original on 4 March 2016. Retrieved 5 April 2016.
  4. ^ a b "FLUOXETINE oral - Essential drugs". medicalguidelines.msf.org. Archived from the original on 29 August 2021. Retrieved 30 August 2020.
  5. ^ 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.
  6. ^ 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.
  7. ^ "WHOCC – ATC/DDD Index". www.whocc.no. Archived from the original on 7 August 2020. Retrieved 27 August 2020.
  8. ^ a b "Fluoxetine Pregnancy and Breastfeeding Warnings". Archived from the original on 31 August 2017. Retrieved 2 December 2015.
  9. ^ Myers, Richard L. (2007). The 100 most important chemical compounds: a reference guide (1st ed.). Westport, Conn.: Greenwood Press. p. 128. ISBN 978-0-313-33758-1.
  10. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  11. ^ Frye JE, Johnson K, eds. (2014). "Fluoxetine" (PDF). International Drug Price Indicator Guide. Medford, Massachusetts: Management Sciences for Health. Archived (PDF) from the original on 24 February 2021. Retrieved 9 August 2020.
  12. ^ "The Top 300 of 2020". ClinCalc. Archived from the original on 12 February 2021. Retrieved 11 April 2020.
  13. ^ "Fluoxetine Hydrochloride - Drug Usage Statistics". ClinCalc. 23 December 2019. Archived from the original on 11 April 2020. Retrieved 11 April 2020.
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