2318. Citalopram

Nomenclature

CAS number: 59729-33-8
1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarbonitrile; 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-5-phthalancarbonitrile; nitalapram; Lu-10-171.
C20H21FN2O; mol wt 324.39.
C 74.05%, H 6.53%, F 5.86%, N 8.64%, O 4.93%.

Description and references

Selective serotonin reuptake inhibitor (SSRI). Prepn: K. P. Boegesoe, A. S. Toft, DE 2657013; eidem, US 4136193 (1977, 1979 both to Kefalas); A. J. Bigler et al., Eur. J. Med. Chem. - Chim. Ther. 12, 289 (1977). Prepn of enantiomers: K. P. Boegesoe, J. Perregaard, EP 347066; eidem, US 4943590, reissued as US RE 34712 (1989, 1990, 1994 all to Lundbeck). Pharmacology: A. V. Christensen et al., Eur. J. Pharmacol. 41, 153 (1977). HPLC determn in plasma and urine: E. Oyehaug et al., J. Chromatogr. 308, 199 (1984). Comparative biotransformation of enantiomers: L. L. Von Moltke et al., Drug Metab. Dispos. 29, 1102 (2001). Evaluation of suicidality risk: G. Laje et al., Am. J. Psychiatry 164, 1530 (2007). Review of clinical pharmacokinetics: K. Brosen, C. A. Naranjo, Eur. Neuropsychopharmacol. 11, 275-283 (2001). Review of clinical experience in depression: M. B. Keller, J. Clin. Psychiatry 61, 896-908 (2000); of escitalopram in depression: P. Malin et al., Expert Rev. Neurother. 4, 769-779 (2004); in anxiety disorders: D. S. Baldwin, R. V. Nair, ibid. 5, 443-449 (2005); S. R. Bareggi et al., Expert Opin. Drug Metab. Toxicol. 3, 741-753 (2007).

Chemical structure

Properties

bp0.03 175-181°.

Derivative

Hydrobromide.

Nomenclature

CAS number: 59729-32-7
Celexa (Forest); Cipramil (Lundbeck); Elopram (Recordati); Seropram (Lundbeck).
C20H21FN2O.HBr; mol wt 405.30.
C 59.27%, H 5.47%, F 4.69%, N 6.91%, O 3.95%, Br 19.71%.

Properties

Fine, white to off-white powder. Crystals from isopropanol, mp 182-183°. Sol in ethanol; sparingly sol in water.

Derivative

Escitalopram.

Nomenclature

CAS number: 128196-01-0
S-(+)-Citalopram.

Properties

[α]D +12.33° (c = 1 in methanol).

Derivative

Escitalopram oxalate.

Nomenclature

CAS number: 219861-08-2
Lu-26-054-0; Cipralex (Lundbeck); Gaudium (Recordati); Lexapro (Forest).
C20H21FN2O.C2H2O4; mol wt 414.43.
C 63.76%, H 5.59%, F 4.58%, N 6.76%, O 19.30%.

Properties

Fine white to slightly yellow powder. Crystals from acetone, mp 147-148°. [α]D +12.31° (c = 1 in methanol). Freely sol in methanol, DMSO; sol in isotonic saline; sparingly sol in water, ethanol; slightly sol in ethyl acetate. Insol in heptane.

Therapeutic Category

Antidepressant. Escitalopram as antidepressant, anxiolytic.

Keywords

Antidepressant; Bicyclics; Serotonin Uptake Inhibitor

Escitalopram: Antidepressant; Bicyclics; Anxiolytic; Serotonin Uptake Inhibitor