3465. Duloxetine

Nomenclature

CAS number: 116539-59-4
S)-N-Methyl-γ-(1-naphthalenyloxy)-2-thiophenepropanamine; (+)-(S)-N-methyl-γ-(1-naphthyloxy)-2-thiophenepropylamine; (+)-N-methyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine; LY-248686.
C18H19NOS; mol wt 297.41.
C 72.69%, H 6.44%, N 4.71%, O 5.38%, S 10.78%.

Description and references

Selective serotonin and norepinephrine reuptake inhibitor (SNRI). Prepn: D. W. Robertson et al., EP 273658; eidem, US 5023269 (1988, 1991 both to Lilly); and abs config: J. Deeter et al., Tetrahedron Lett. 31, 7101 (1990). Improved process: R. A. Berglund, US 5362886 (1994 to Lilly). Pharmacology: D. T. Wong et al., Neuropsychopharmacology 8, 23 (1993). Neurochemical effects in vivo: R. W. Fuller et al., J. Pharmacol. Exp. Ther. 269, 132 (1994). Determn of chiral purity: E. C. Rickard, R. J. Bopp, J. Chromatogr. A 680, 609 (1994). Clinical pharmacokinetics: A. Sharma et al., J. Clin. Pharmacol. 40, 161 (2000). Evaluation of suicidality risk: N. Acharya et al., J. Clin. Psychopharmacol. 26, 587 (2006). Clinical trial in diabetic neuropathic pain: D. K. Kajdasz et al., Clin. Ther. 29, 2536 (2007); in fibromyalgia: L. M. Arnold et al., J. Womens Health 16, 1145 (2007). Review of mechanism of action: K. B. Thor et al., Int. J. Clin. Pract. 61, 1349-1355 (2007). Review of clinical experience in depression: M. Bauer et al., Expert Opin. Pharmacother. 7, 421-427 (2006); in stress urinary incontinence: P. Mariappan et al., Eur. Urol. 51, 67-74 (2007); in generalized anxiety disorder: C. Allgulander et al., Curr. Med. Res. Opin. 23, 1245-1252 (2007).

Chemical structure

Derivative

Hydrochloride.

Nomenclature

CAS number: 136434-34-9
Ariclaim (Lilly); Cymbalta (Lilly); Yentreve (Lilly).
C18H19NOS.HCl; mol wt 333.88.
C 64.75%, H 6.04%, N 4.20%, O 4.79%, S 9.60%, Cl 10.62%.

Properties

White to slightly brownish white solid. pKa in DMF-water (66:34): 9.6. Slightly sol in water.

Therapeutic Category

Antidepressant; anxiolytic. In treatment of stress urinary incontinence; in diabetic peripheral neuropathic pain.

Keywords

Antidepressant; Serotonin Noradrenaline Reuptake Inhibitor (SNRI); Anxiolytic