Agomelatine

Title: Agomelatine
CAS Registry Number: 138112-76-2
CAS Name: N-[2-(7-Methoxy-1-naphthalenyl)ethyl]acetamide
Manufacturers' Codes: S-20098
Trademarks: Valdoxan (Biopharma)
Molecular Formula: C15H17NO2
Molecular Weight: 243.30
Percent Composition: C 74.05%, H 7.04%, N 5.76%, O 13.15%
Literature 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. Lôo et al., Int. Clin. Psychopharmacol. 17, 239 (2002); S. H. Kennedy, R. Emsley, Eur. Neuropsychopharmacol. 16, 93 (2006).
Properties: Crystals from toluene + hexane, 2:1, mp 109-110°.
Melting point: mp 109-110°
Therap-Cat: Antidepressant.
Keywords: Serotonin Receptor Antagonist; Antidepressant.
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Agomelatine
Agomelatine2DACS.svg
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Systematic (IUPAC) name
N-[2-(7-methoxynaphthalen-1-yl)ethyl]acetamide
Clinical data
Trade names Melitor, Thymanax, Valdoxan
AHFS/Drugs.com International Drug Names
Licence data EMA:Link
Pregnancy cat. B1 (AU)
Legal status Prescription Only (S4) (AU) POM (UK)
Routes Oral
Pharmacokinetic data
Bioavailability 80%[1]
Protein binding 95%[1]
Metabolism hepatic (90% CYP1A2 and 10% CYP2C9)[1]
Half-life 1-2 hours[1]
Excretion Renal (80%, mostly as metabolites)[1]
Identifiers
CAS number 138112-76-2 N
ATC code N06AX22
PubChem CID 82148
IUPHAR ligand 198
ChemSpider 74141 YesY
UNII 137R1N49AD YesY
KEGG D02578 YesY
ChEMBL CHEMBL10878 YesY
Chemical data
Formula C15H17NO2 
Mol. mass 243.301
 N (what is this?)  (verify)

Agomelatine (BAN, rINN; trade names Valdoxan, Melitor, Thymanax) is a melatonergic antidepressant developed by the pharmaceutical company Servier. It is marketed for the treatment of major depressive disorder and has been reported to not produce discontinuation syndrome and have no sexual side effects compared to SSRIs, SNRIs and the older tricyclic antidepressants. Agomelatine may also have positive effects on sleep.