7043. Paroxetine

Nomenclature

CAS number: 61869-08-7
(3S,4R)-3-[(1,3-Benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine; (-)-trans-4-(p-fluorophenyl)-3-[[3,4-(methylenedioxy)phenoxy]methyl]piperidine; FG-7051; BRL-29060.
C19H20FNO3; mol wt 329.37.
C 69.28%, H 6.12%, F 5.77%, N 4.25%, O 14.57%.

Description and 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). Electroanalytical determn in pharmaceuticals: H. P. A. Nouws et al., J. Pharm. Biomed. Anal. 42, 341 (2006). 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); of clinical efficacy of controlled-release formulation: C.-U. Pae, A. A. Patkar, Expert Rev. Neurother. 7, 107-120 (2007).

Chemical structure

Derivative

Hydrochloride hemihydrate.

Nomenclature

CAS number: 110429-35-1; 78246-49-8 (hydrochloride)
Aropax (GSK); Deroxat (GSK); ParoLich (Winthrop); Paroxat (Hexal); Paxil (GSK); Seroxat (GSK); Tagonis (GSK).
C19H20FNO3.HCl. 1/2 H2O; mol wt 374.83.
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.

Derivative

Maleate.

Nomenclature

CAS number: 64006-44-6

Properties

Crystals from ethanol-ether, mp 136-138°. [α]D -87° (c = 5 in ethanol). LD50 in mice (mg/kg): 845 s.c.; 500 orally (Christensen, Squires, 1977).

Derivative

Methanesulfonaate.

Nomenclature

CAS number: 217797-14-3
Paroxetine mesylate; Divarius (Chiesi); Euplix (Desitin); Pexeva (JDS).
C19H20FNO3.CH4O3S; mol wt 425.47.
C 56.46%, H 5.69%, F 4.47%, N 3.29%, O 22.56%, S 7.54%.

Properties

Odorless, off-white powder, mp 147-150°. Soly in water: >1g/ml.

Therapeutic Category

Antidepressant; antiobsessional.

Therapeutic Category (Veterinary)

In treatment of canine and feline behavioral disorders.

Keywords

Antidepressant; Bicyclics; Serotonin Uptake Inhibitor; Antiobsessional