4185. Fluoxetine

Nomenclature

CAS number: 54910-89-3
N-Methyl-γ-[4-(trifluoromethyl)phenoxy]benzenepropanamine; (±)-N-methyl-3-phenyl-3-[(α,α,α-trifluoro-p-tolyl)oxy]propylamine; dl-N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine.
C17H18F3NO; mol wt 309.33.
C 66.01%, H 5.87%, F 18.43%, N 4.53%, O 5.17%.

Description and 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); in post-traumatic stress disorder: F. Martenyi, V. Soldatenkova, ibid. 16, 340 (2006). Veterinary trial in canine aggression: N. H. Dodman et al., J. Am. Vet. Med. Assoc. 209, 1585 (1996). Evaluation of suicidality risk: R. H. Perlis et al., Psychother. Psychosom. 76, 40 (2007). 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: T. Pearlstein, K. A. Yonkers, Expert Opin. Pharmacother. 3, 979-991 (2002); in anorexia nervosa: S. S. Kim, Ann. Pharmacother. 37, 890-892 (2003); of safety profile: J. F. Wernicke, Expert Opin. Drug Saf. 3, 495-504 (2004); of discovery and clinical development: D. T. Wong et al., Nat. Rev. Drug Discovery 4, 764-774 (2005).

Chemical structure

Derivative

Hydrochloride.

Nomenclature

CAS number: 59333-67-4
LY-110140; Adofen (Ferrer); Fluctin (Lilly); Fluneurin (Hexal); Fluoxeren (Menarini); Fluox-Puren (Alpharma); Flusol (Ecosol); Fluxet (Krewel); Fontex (Lilly); Foxetin (Gador); Lovan (Lilly); Prozac (Lilly); Reconcile (Lilly); Sarafem (Lilly).
C17H18F3NO.HCl; mol wt 345.79.
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).

Derivative

Oxalate.
C19H18F3NO5; mol wt 397.35.
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).

Therapeutic Category

Antidepressant; antiobessional; antibulimic.

Therapeutic Category (Veterinary)

In treatment of behavioral disorders in dogs and cats.

Keywords

Antidepressant; Serotonin Uptake Inhibitor; Antiobsessional