File:Seproxetine.svg · Wikimedia Commons · See Wikimedia Commons
fluoxetine
Sign in to saveAlso known as Prozac
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.
OverviewAI-generated
Fluoxetine is a chemical compound with the formula C₁₇H₁₈F₃NO. Its IUPAC name is N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine. The substance has a mass of 309.134049 and a weight of 309.33. It features a defined daily dose of 20 and a price of 0.11. The stylized name for the compound is FLUoxetine.
Chemical properties include a charge of 0, an xlogp value of 4, and a topological polar surface area of 21.3. The molecule contains one hydrogen bond donor and five hydrogen bond acceptors. Its canonical SMILES notation is CNCCC(C1=CC=CC=C1)OC2=CC=C(C=C2)C(F)(F)F. Fluoxetine is referenced by 3,295 other encyclopedia articles and has 17,088 associated PubMed entries.
Synthesized by Vinony from 20 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Key facts
- Drug.verifiedrevid
- 456481815
- Drug.image
- Fluoxetine.svg
- Drug.image_class
- skin-invert-image
- Drug.image2
- R-and-S-fluoxetine-enantiomers-based-on-HCl-xtal-Mercury-3D-balls.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 250
- Drug.caption
- (R)-fluoxetine (left), (S)-fluoxetine (right)
- Drug.chirality
- Racemic mixture
- Drug.pronounce
- US: UK:
- Drug.tradename
- Prozac, Sarafem, others
- Drug.MedlinePlus
- a689006
- Drug.DailyMedID
- Fluoxetine
- Drug.pregnancy_AU
- C
- Drug.addiction_liability
- None
- Drug.routes_of_administration
- By mouth
- Drug.class
- Selective serotonin reuptake inhibitor (SSRI)
- Drug.ATC_prefix
- N06
- Drug.ATC_suffix
- AB03
via Wikipedia infobox
Chemical data
- Formula
- C17H18F3NO
- Molecular weight
- 309.33 g/mol
- IUPAC name
- N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine
- SMILES
- CNCCC(C1=CC=CC=C1)OC2=CC=C(C=C2)C(F)(F)F
- InChIKey
- RTHCYVBBDHJXIQ-UHFFFAOYSA-N
- XLogP
- 4
- Polar surface area
- 21.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Research
17,088 papers- Clinical pharmacokinetics of fluoxetine.ReviewClinical pharmacokinetics · 1994Altamura AC, Moro AR, Percudani MDOI: 10.2165/00003088-199426030-00004
- Fluoxetine. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in depressive illness.ReviewDrugs · 1986Benfield P, Heel RC, Lewis SPDOI: 10.2165/00003495-198632060-00002
- Fluoxetine.ReviewThe New England journal of medicine · 1994Gram LDOI: 10.1056/NEJM199411173312008
- Once-weekly fluoxetine.ReviewDrugs · 2001Wagstaff AJ, Goa KLDOI: 10.2165/00003495-200161150-00006
- Fluoxetine: a five-year review.ReviewClinical therapeutics · 1993Stokes PE
- Fluoxetine drug-drug interactions. II.ReviewJournal of clinical psychopharmacology · 1990Ciraulo DA, Shader RI
- [Fluoxetine].ReviewMedicina (Florence, Italy) · 1989Tiraboschi P, Spagnoli A
- Fluoxetine: a case history of its discovery and preclinical development.ReviewExpert opinion on drug discovery · 2014Perez-Caballero L, Torres-Sanchez S, Bravo L et al.DOI: 10.1517/17460441.2014.907790
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Has part
- hydrogen
- Mass
- 309.134049
- Has use
- medication
Show 14 more facts
- defined daily dose
- 20
- significant drug interaction
- (RS)-citalopram
- Commons category
- Fluoxetine
- chemical formula
- C₁₇H₁₈F₃NO
- World Health Organisation international non-proprietary name
- fluoxetine
- medical condition treated
- anxiety disorder
- price
- 0.11
- canonical SMILES
- CNCCC(C1=CC=CC=C1)OC2=CC=C(C=C2)C(F)(F)F
- subject has role
- essential medicine
- physically interacts with
- solute carrier family 6 member 4
- found in taxon
- Hordeum vulgare
- route of administration
- oral administration
- stylized name
- FLUoxetine
- legal status (medicine)
- boxed warning
Sources (11)
via Wikidata · CC0
~32 min read
Encyclopedic overview
34 sectionsContents
- Medical uses
- Depression
- Obsessive–compulsive disorder
- Panic disorder
- Bulimia nervosa
- Premenstrual dysphoric disorder
- Impulsive aggression
- Obesity and overweight adults
- Special populations
- Adverse effects
- Sexual dysfunction
- Withdrawal
- Pregnancy
- Suicide
- QT prolongation
- Overdose
- Interactions
- Pharmacology
- Pharmacodynamics
- Mechanism of action
- Pharmacokinetics
- Measurement in body fluids
- History
- Society and culture
- Prescription trends
- Environmental effects
- Politics
- American aircraft pilots
- Research
- Veterinary use
- See also
- References
- Further reading
- External links
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, 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.
Excerpted from Wikipedia’s “fluoxetine” article, available under the CC BY-SA 4.0 licence.