190. Agomelatine

Nomenclature

CAS number: 138112-76-2
N-[2-(7-Methoxy-1-naphthalenyl)ethyl]acetamide; S-20098; Valdoxan (Biopharma).
C15H17NO2; mol wt 243.30.
C 74.05%, H 7.04%, N 5.76%, O 13.15%.

Description and references

Melatoninergic agonist and selective serotonin 5-HT2B and 5-HT2C receptor antagonist; metabolically stable analogue of melatonin, q.v. Prepn: J. Andrieux et al., EP 447285; eidem, US 5225442 (1991, 1993 both to Adir); and structure-activity studies: S. Yous et al., J. Med. Chem. 35, 1484 (1992); P. Depreux et al., ibid. 37, 3231 (1994). Mechanism of action: M. J. Millan et al., J. Pharmacol. Exp. Ther. 306, 954 (2003). Clinical evaluation in major depressive disorder: H. Lo et al., Int. Clin. Psychopharmacol. 17, 239 (2002); S. H. Kennedy, R. Emsley, Eur. Neuropsychopharmacol. 16, 93 (2006).

Chemical structure

Properties

Crystals from toluene + hexane, 2:1, mp 109-110°.

Therapeutic Category

Antidepressant.

Keywords

Serotonin Receptor Antagonist; Antidepressant