Dapoxetine

Title: Dapoxetine
CAS Registry Number: 119356-77-3
CAS Name: (aS)-N,N-Dimethyl-a-[2-(1-naphthalenyloxy)ethyl]benzenemethanamine
Additional Names: (+)-N,N-dimethyl-1-phenyl-3-(1-naphthalenyloxy)propanamine
Manufacturers' Codes: LY-210448
Molecular Formula: C21H23NO
Molecular Weight: 305.41
Percent Composition: C 82.59%, H 7.59%, N 4.59%, O 5.24%
Literature References: Selective serotonin reuptake inhibitor (SSRI). Prepn: D. W. Robertson et al., EP 288188; eidem, US 5135947 (1988, 1992 both to Lilly). Chiral synthesis: W. J. Wheeler, D. D. O'Bannon, J. Labelled Compd. Radiopharm. 31, 305 (1992). HPLC determn in plasma: C. L. Hamilton, J. D. Cornpropst, J. Chromatogr. 612, 253 (1993). Review of pharmacology and clinical experience: B. Feret, Formulary 40, 227-230 (2005).
Derivative Type: Hydrochloride
CAS Registry Number: 129938-20-1
Molecular Formula: C21H23NO.HCl
Molecular Weight: 341.87
Percent Composition: C 73.78%, H 7.08%, N 4.10%, O 4.68%, Cl 10.37%
Properties: White crystalline solid from hydrochloric acid and ethyl acetate. [a]D +135.78° (c = 2.18 in methanol).
Optical Rotation: [a]D +135.78° (c = 2.18 in methanol)
Therap-Cat: In treatment of premature ejaculation.
Keywords: Serotonin Uptake Inhibitor.
Dapsone Daptomycin D-Araboflavin Darbepoetin Alfa Darifenacin

Dapoxetine
Dapoxetine Structural Formulae V.1.svg
Systematic (IUPAC) name
(S)-N,N-dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine
Clinical data
Trade names Kutub, Priligy, Duratia, Pentenal-30, Sustinex
AHFS/Drugs.com International Drug Names
Legal status Prescription only
Routes Oral
Pharmacokinetic data
Half-life 1.5–1.6 h
Identifiers
CAS number 119356-77-3
129938-20-1 (HCl salt)
ATC code G04BX14
PubChem CID 71353
ChemSpider 64453
UNII GB2433A4M3 YesY
KEGG D03649
Chemical data
Formula C21H23NO 
Mol. mass 305.413 g/mol

Dapoxetine, marketed as Priligy (among and other brands) is the first compound developed specially for the treatment of premature ejaculation (PE) in men 18–64 years old.[1][2] Dapoxetine works by inhibiting the serotonin transporter, increasing serotonin’s action at the post synaptic cleft, and as a consequence promoting ejaculatory delay.[3] As a member of selective serotonin reuptake inhibitor (SSRI) family, dapoxetine was initially created as an antidepressant. However, unlike other SSRIs, dapoxetine is absorbed and eliminated rapidly in the body. Its fast acting property makes it suitable for the treatment of PE but not as an antidepressant.[4]

Originally created by Eli Lilly pharmaceutical company, dapoxetine was sold to Johnson & Johnson in 2003 and submitted as a new drug application to the Food and Drug Administration (FDA) for the treatment of PE in 2004.[5] Dapoxetine has been sold in several European and Asian countries, and lately in Mexico. In the US, dapoxetine is in phase III development and expected to be marketed soon.[3] In 2012, Menarini acquired the rights to commercialise Priligy in Europe, most of Asia, Africa, Latin America and the Middle East.[6]