Structure via PubChem · Public domain (PubChem)
dapoxetine
Sign in to saveAlso known as LY 210448, LY-210448, Dapoxetina, Dapoxetinum
Dapoxetine, sold under the brand name Priligy among others, is a selective serotonin reuptake inhibitor (SSRI) used for the treatment of premature ejaculation (PE) in men ages 18 to 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 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
Chemical data
- Formula
- C21H23NO
- Molecular weight
- 305.4 g/mol
- IUPAC name
- (1S)-N,N-dimethyl-3-naphthalen-1-yloxy-1-phenylpropan-1-amine
- SMILES
- CN(C)[C@@H](CCOC1=CC=CC2=CC=CC=C21)C3=CC=CC=C3
- InChIKey
- USRHYDPUVLEVMC-FQEVSTJZSA-N
- XLogP
- 5.1
- Polar surface area
- 12.5 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 305.177964
Show 5 more facts
- Commons category
- Dapoxetine
- chemical formula
- C₂₁H₂₃NO
- defined daily dose
- 30
- isomeric SMILES
- CN(C)[C@@H](CCOC1=CC=CC2=CC=CC=C21)C3=CC=CC=C3
- canonical SMILES
- CN(C)C(CCOC1=CC=CC2=CC=CC=C21)C3=CC=CC=C3
Sources (3)
via Wikidata · CC0
~10 min read
Article
20 sectionsContents
- Medical uses
- Premature ejaculation
- Depression and anxiety
- Contraindications
- Adverse effects
- Overdose
- Interactions
- Phosphodiesterase 5 inhibitors
- Alcohol
- Pharmacology
- Mechanism of action
- Pharmacokinetics
- Safety and tolerability
- Cardiovascular safety
- Neurocognitive safety
- Withdrawal
- Synthesis
- Regulatory history
- See also
- References
Dapoxetine, sold under the brand name Priligy among others, is a selective serotonin reuptake inhibitor (SSRI) used for the treatment of premature ejaculation (PE) in men ages 18 to 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 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.
Originally created by Eli Lilly pharmaceutical company, dapoxetine was sold to Johnson & Johnson in 2003 and submitted as a New Drug Application to the US 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 Pharmaceuticals to market dapoxetine in the United States, 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.