Paroxetine
Title: Paroxetine
CAS Registry Number: 61869-08-7
CAS Name: (3S-trans)-3-[(1,3-Benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine
Additional Names: (-)-trans-4-(p-fluorophenyl)-3-[[3,4-(methylenedioxy)phenoxy]methyl]piperidine
Manufacturers' Codes: FG-7051; BRL-29060
Molecular Formula: C19H20FNO3
Molecular Weight: 329.37
Percent Composition: C 69.28%, H 6.12%, F 5.77%, N 4.25%, O 14.57%
Literature References: Selective serotonin (5-HT) reuptake inhibitor (SSRI). Prepn: J. A. Christensen, R. F. Squires, DE 2404113; eidem, US 3912743; US 4007196 (1974, 1975, 1977 all to Ferrosan); of crystalline hydrochloride hemihydrate: R. D. B. Barnes et al., EP 223403; US 4721723 (1987, 1988 both to Beecham). Characterization of serotonin inhibition: J. Buus Lassen, Eur. J. Pharmacol. 47, 351 (1978). Binding to serotonin transporter complex: E. Habert et al., ibid. 118, 107 (1985). Clinical pharmacokinetics: J. Lund et al., Acta Pharmacol. Toxicol. 51, 351 (1982). HPLC determn in plasma: M. A. Brett et al., J. Chromatogr. 419, 438 (1987). Clinical trial in obsessive-compulsive disorder: J. Zohar et al., Br. J. Psychiatry 169, 468 (1996); in social phobia: M. B. Stein et al., J. Am. Med. Assoc. 280, 708 (1998). Review of pharmacology and clinical use in depression: K. L. Dechant, S. P. Clissold, Drugs 41, 225-253 (1991); of clinical experience: D. Dunner, R. Kumar, Pharmacopsychiatry 31, 89-101 (1998); of use in generalized social anxiety disorder: M. Van Ameringen et al., Expert Opin. Pharmacother. 6, 819-830 (2005).
 
Derivative Type: Hydrochloride hemihydrate
CAS Registry Number: 110429-35-1; 78246-49-8 (hydrochloride)
Trademarks: Aropax (GSK); Deroxat (GSK); Paxil (GSK); Seroxat (GSK)
Molecular Formula: C19H20FNO3.HCl.½H2O
Molecular Weight: 374.83
Percent Composition: C 60.88%, H 5.92%, F 5.07%, N 3.74%, O 14.94%, Cl 9.46%
Properties: Crystals, mp 129-131°. Soly in water: 5.4 mg/ml.
Melting point: mp 129-131°
 
Derivative Type: Maleate
CAS Registry Number: 64006-44-6
Properties: Crystals from ethanol-ether, mp 136-138°. [a]D -87° (c = 5 in ethanol). LD50 in mice (mg/kg): 845 s.c.; 500 orally (Christensen, Squires, 1977).
Melting point: mp 136-138°
Optical Rotation: [a]D -87° (c = 5 in ethanol)
Toxicity data: LD50 in mice (mg/kg): 845 s.c.; 500 orally (Christensen, Squires, 1977)
 
Therap-Cat: Antidepressant; antiobsessional.
Keywords: Antidepressant; Bicyclics; Serotonin Uptake Inhibitor; Antiobsessional.

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