Fluoxetine

Title: Fluoxetine
CAS Registry Number: 54910-89-3
CAS Name: N-Methyl-g-[4-(trifluoromethyl)phenoxy]benzenepropanamine
Additional Names: (±)-N-methyl-3-phenyl-3-[(a,a,a-trifluoro-p-tolyl)oxy]propylamine; dl-N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine
Molecular Formula: C17H18F3NO
Molecular Weight: 309.33
Percent Composition: C 66.01%, H 5.87%, F 18.43%, N 4.53%, O 5.17%
Literature References: Selective serotonin reuptake inhibitor (SSRI). Prepn: B. B. Malloy, K. K. Schmiegel, DE 2500110; eidem, US 4314081 (1975, 1982 both to Lilly). Pharmacology: D. T. Wong et al., Life Sci. 15, 471 (1974). GC determn in plasma: J. F. Nash et al., Clin. Chem. 28, 2100 (1982). Series of articles on clinical pharmacology and therapeutic efficacy in depression: J. Clin. Psychiatry 46, Suppl. 3(2), 2-67 (1985). Toxicity data: P. Stark et al., ibid. 7. Clinical trial in bulimia nervosa: D. J. Goldstein et al., Br. J. Psychiatry 166, 660 (1995); in obsessive-compulsive disorder: J. J. Lopez-Ibor, Jr. et al., Eur. Neuropsychopharmacol. 6, 111 (1996). Veterinary trial in canine aggression: N. H. Dodman et al., J. Am. Vet. Med. Assoc. 209, 1585 (1996). Comprehensive description: D. S. Risley, R. J. Bopp, Anal. Profiles Drug Subs. 19, 193-219 (1990). Review of clinical experience: P. E. Stokes, A. Holtz, Clin. Ther. 19, 1135-1250 (1997); in premenstrual dysphoric disorder: S. Romano et al., Clin. Ther. 21, 615 (1999).
Derivative Type: Hydrochloride
CAS Registry Number: 59333-67-4
Manufacturers' Codes: LY-110140
Trademarks: Adofen (Ferrer); Fluctin (Lilly); Fluoxeren (Menarini); Fontex (Lilly); Foxetin (Gador); Lovan (Lilly); Prozac (Lilly); Reneuron (Juste); Sarafem (Lilly)
Molecular Formula: C17H18F3NO.HCl
Molecular Weight: 345.79
Percent Composition: C 59.05%, H 5.54%, F 16.48%, N 4.05%, O 4.63%, Cl 10.25%
Properties: White to off-white crystalline solid. mp 158.4-158.9°. Soly (mg/ml): methanol, ethanol >100; acetone, acetonitrile, chloroform 33-100; dichloromethane 5-10; ethyl acetate 2-2.5; toluene, cyclohexane, hexane 0.5-0.67. Maximum soly in water: 14 mg/ml. uv max (methanol) 227, 264, 268, 275 nm (E1%1cm 372.0, 29.2, 29.3, 21.5). LD50 in mice, rats (mg/kg): 248, 452 orally (Stark).
Melting point: mp 158.4-158.9°
Absorption maximum: uv max (methanol) 227, 264, 268, 275 nm (E1%1cm 372.0, 29.2, 29.3, 21.5)
Toxicity data: LD50 in mice, rats (mg/kg): 248, 452 orally (Stark)
Derivative Type: Oxalate
Molecular Formula: C19H18F3NO5
Molecular Weight: 397.35
Percent Composition: C 57.43%, H 4.57%, F 14.34%, N 3.53%, O 20.13%
Properties: Crystals from ethyl acetate-methanol, mp 179-182° (dec).
Melting point: mp 179-182° (dec)
Therap-Cat: Antidepressant; antiobessional; antibulimic.
Keywords: Antidepressant; Serotonin Uptake Inhibitor; Antiobsessional.
Fluoxymesterone Flupentixol Fluperolone Acetate Fluphenazine Flupirtine

Fluoxetine
Fluoxetine2DACS.svg
Fluoxetine3Dan3.gif
Systematic (IUPAC) name
(RS)-N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine
Clinical data
Trade names Prozac, among others
AHFS/Drugs.com monograph
MedlinePlus a689006
Licence data US FDA:link
Pregnancy cat. C (AU) C (US)
Legal status Prescription Only (S4) (AU) -only (CA) POM (UK) -only (US)
Routes Oral
Pharmacokinetic data
Bioavailability 72%[1]
Protein binding 94-95%[1][2][3][4][5]
Metabolism Hepatic (mostly CYP2D6-mediated)[1][2][3][4][5]
Half-life 1–3 days (acute)
4–6 days (chronic)[1][2][3][4][5]
Excretion Urine (80%), faeces (15%)[1][2][3][4][5]
Identifiers
CAS number 54910-89-3 YesY  YesY
ATC code N06AB03
PubChem CID 3386
IUPHAR ligand 203
DrugBank DB00472
ChemSpider 3269 YesY
UNII 01K63SUP8D YesY
KEGG D00823 N
ChEBI CHEBI:5118 YesY
ChEMBL CHEMBL41 YesY
Chemical data
Formula C17H18F3NO 
Mol. mass 309.33 g·mol−1
Physical data
Melt. point 179–182 °C (354–360 °F)
Boiling point 395 °C (743 °F)
Solubility in water 14 mg/mL (20 °C)
 N (what is this?)  (verify)

Fluoxetine (also known by the tradenames Prozac, Sarafem, Ladose and Fontex, among others) is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. Fluoxetine was first documented in 1974 by scientists from Eli Lilly and Company.[6] It was presented to the U.S. Food and Drug Administration in February 1977, with Eli Lilly receiving final approval to market the drug in December 1987. Fluoxetine went off-patent in August 2001.[7]

Fluoxetine is approved in the US for the treatment of major depression (including pediatric depression), obsessive-compulsive disorder (in both adult and paediatric populations), bulimia nervosa, panic disorder and premenstrual dysphoric disorder.[8] In addition, fluoxetine is used to treat trichotillomania if cognitive behaviour therapy is unsuccessful.[9] In combination with the atypical antipsychotic olanzapine it is known by a few brand names,[note 1] including its US brand name Symbyax, which is approved for the treatment of depressive episodes as part of bipolar I disorder and in the treatment of treatment-resistant depression.

Despite the availability of newer agents, fluoxetine remains extremely popular. In 2010, over 24.4 million prescriptions for generic formulations of fluoxetine were filled in the United States alone,[10] making it the third most prescribed antidepressant after sertraline (SSRI; became generic in 2006) and citalopram (SSRI; became generic in 2003).[10] In 2011, 6 million prescriptions for fluoxetine were handed out in the UK.[11]