Dapoxetine

Dapoxetine, marketed as Priligy, among others, is a selective serotonin reuptake inhibitor (SSRI) used for the treatment of premature ejaculation (PE) in men 18–64 years old. Dapoxetine works by inhibiting the serotonin transporter, increasing serotonin's action at the postsynaptic cleft, and as a consequence promoting ejaculatory delay. As a member of the 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.

Dapoxetine
Clinical data
Trade namesEJ-30, Priligy, others (see below)
AHFS/Drugs.comInternational Drug Names
Routes of
administration
Oral (tablets)
ATC code
Legal status
Legal status
  • BR: Class C1 (Other controlled substances)
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability15–76% (mean 42%), Tmax = 1–1.3 hours
Protein binding>99%
MetabolismLiver (CYP2D6, CYP3A4), kidney (FMO1)
MetabolitesDapoxetine-N-oxide, desmethyldapoxetine, didesmethyldapoxetine
Elimination half-life1.5–1.6 h
ExcretionKidneys
Identifiers
  • (S)-N,N-Dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H23NO
Molar mass305.421 g·mol−1
3D model (JSmol)
SMILES
  • CN(C)[C@@H](CCOc1cccc2ccccc12)c1ccccc1
  • InChI=1S/C21H23NO/c1-22(2)20(18-10-4-3-5-11-18)15-16-23-21-14-8-12-17-9-6-7-13-19(17)21/h3-14,20H,15-16H2,1-2H3/t20-/m0/s1
  • Key:USRHYDPUVLEVMC-FQEVSTJZSA-N

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. Dapoxetine is sold in several European and Asian countries, and in Mexico. In the US, dapoxetine has been in phase III development. In May 2012, US-based Furiex Pharmaceuticals reached an agreement with ALZA Corp and Janssen Pharmaceutica to market dapoxetine in the USA, Japan, and Canada, while selling the rights to market the drug in Europe, most of Asia, Africa, Latin America, and the Middle East to Menarini.

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