Prozac

Fluoxetine

Fluoxetine (top), (R)-fluoxetine (center), (S)-fluoxetine (bottom)
Clinical data
Trade names	Prozac, Sarafem, Adofen, other
AHFS/Drugs.com	Monograph
MedlinePlus	a689006
License data	US FDA: Fluoxetine
Pregnancy category	AU: C US: C (Risk not ruled out)
Dependence liability	Physical: Low Psychological: Low
Addiction liability	None
Routes of administration	By mouth
ATC code	N06AB03 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	60–80%
Protein binding	94–95%
Metabolism	Liver (mostly CYP2D6-mediated)
Biological half-life	1–3 days (acute) 4–6 days (chronic)
Excretion	Urine (80%), faeces (15%)
Identifiers
IUPAC name N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine
CAS Number	54910-89-3 Y
PubChem CID	3386
IUPHAR/BPS	203
DrugBank	DB00472 Y
ChemSpider	3269 Y
UNII	01K63SUP8D
KEGG	D00326 Y
ChEBI	CHEBI:5118 Y
ChEMBL	CHEMBL41 Y
ECHA InfoCard	100.125.370
Chemical and physical data
Formula	C17H18F3NO
Molar mass	309.33 g·mol−1
3D model (Jmol)	Interactive image
Chirality	Racemic mixture
Melting point	179 to 182 °C (354 to 360 °F)
Boiling point	395 °C (743 °F)
Solubility in water	14 mg/mL (20 °C)
SMILES CNCCC(c1ccccc1)Oc2ccc(cc2)C(F)(F)F
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 Y Key:RTHCYVBBDHJXIQ-UHFFFAOYSA-N Y

Fluoxetine, also known by trade names Prozac and Sarafem among others, is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. It is used for the treatment of major depressive disorder, obsessive–compulsive disorder (OCD), bulimia nervosa, panic disorder, and premenstrual dysphoric disorder. It may decrease the risk of suicide in those over the age of 65. Fluoxetine has also been used to treat premature ejaculation. It is taken by mouth.

Common side effects include trouble sleeping, loss of appetite, dry mouth, rash, and abnormal dreams. 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. If stopped suddenly a withdrawal syndrome may occur with anxiety, dizziness, and changes in sensation. It is unclear if it is safe in pregnancy. If already on the medication it may be reasonable to continue during breastfeeding. Its mechanism of action is not entirely clear but believed to be related to increasing serotonin activity in the brain.

Fluoxetine was discovered 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, the most effective and safe medicines needed in a health system. It is available as a generic medication. The wholesale cost in the developing world is between 0.01 and 0.04 USD per day as of 2014. In the United States it costs about 0.85 USD per day.