Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C21H23NO |
Molecular Weight | 305.4134 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)[C@@H](CCOC1=CC=CC2=C1C=CC=C2)C3=CC=CC=C3
InChI
InChIKey=USRHYDPUVLEVMC-FQEVSTJZSA-N
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
Dapoxetine hydrochloride is a selective serotonin reuptake inhibitor (SSRIs). In addition, dapoxetine inhibits voltage-dependent K+ (Kv) channels in a dose-, time-, use-, and state (open)-dependent manner, independent of serotonin reuptake inhibition. Dapoxetine is indicated for the treatment of premature ejaculation (PE) in men 18 to 64 years of age, who have all of the following: persistent or recurrent ejaculation with minimal sexual stimulation before, on, or shortly after penetration and before the patient wishes; and marked personal distress or interpersonal difficulty as a consequence of PE; and poor control over ejaculation. The mechanism of action of dapoxetine in premature ejaculation is presumed to be linked to the inhibition of neuronal reuptake of serotonin and the subsequent potentiation of the neurotransmitter's action at pre- and post-synaptic receptors. The most common effects when taking dapoxetine are nausea, dizziness, dry mouth, headache, diarrhea, and insomnia.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22906232
Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/9234326
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2362996 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28058743 |
2.68 µM [IC50] | ||
Target ID: CHEMBL228 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16430636 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | PRILIGY Approved UseINDICATIONS. PRILIGY is indicated for the treatment of premature ejaculation (PE) in men 18 to 64 years of age,
who have all of the following: persistent or recurrent ejaculation with minimal sexual stimulation before, on, or shortly after penetration and before the patient wishes; and marked personal distress or interpersonal difficulty as a consequence of PE; and poor control over ejaculation. |
PubMed
Title | Date | PubMed |
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Determination of dapoxetine, an investigational agent with the potential for treating depression, and its mono- and di-desmethyl metabolites in human plasma using column-switching high-performance liquid chromatography. | 1993 Feb 26 |
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Mind over matter: CNS-based approaches to urological diseases. | 2004 Dec |
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The brain leads the way. | 2004 Nov |
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Dapoxetine: LY 210448. | 2005 |
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The era of ESSTIs is slowly approaching? | 2005 Jul |
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Lifelong premature ejaculation: definition, serotonergic neurotransmission and drug treatment. | 2005 Jun |
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New agents in the treatment of premature ejaculation. | 2006 Dec |
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Pharmacokinetic and pharmacodynamic features of dapoxetine, a novel drug for 'on-demand' treatment of premature ejaculation. | 2006 Feb |
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Dapoxetine, a novel treatment for premature ejaculation, does not have pharmacokinetic interactions with phosphodiesterase-5 inhibitors. | 2006 Jan-Feb |
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Just hold on a minute (or should it be two?). | 2006 Jul |
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Treatment of premature ejaculation: new drugs and treatment strategies. | 2006 Nov |
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Dapoxetine for treatment of premature ejaculation. | 2006 Nov 11 |
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Pharmacokinetics of dapoxetine, a new treatment for premature ejaculation: Impact of age and effects of a high-fat meal. | 2006 Sep |
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Efficacy and tolerability of dapoxetine in treatment of premature ejaculation: an integrated analysis of two double-blind, randomised controlled trials. | 2006 Sep 9 |
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Medical therapy for premature ejaculation. | 2006 Sep 9 |
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Comparison of dapoxetine versus paroxetine in patients with premature ejaculation: a double-blind, placebo-controlled, fixed-dose, randomized study. | 2006 Sep-Oct |
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Premature ejaculation. | 2007 Apr |
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Effect of acute dapoxetine administration on the pudendal motoneuron reflex in anesthetized rats: comparison with paroxetine. | 2007 Jan |
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Development of in situ ion selective sensors for dissolution. | 2007 Jan 2 |
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The majority of men with lifelong premature ejaculation prefer daily drug treatment: an observation study in a consecutive group of Dutch men. | 2007 Jul |
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Dapoxetine, a novel selective serotonin transport inhibitor for the treatment of premature ejaculation. | 2007 Jun |
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Selective serotonin reuptake inhibitors in the treatment of premature ejaculation. | 2007 Jun 5 |
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Dapoxetine has no pharmacokinetic or cognitive interactions with ethanol in healthy male volunteers. | 2007 Mar |
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Regarding Waldinger and Schweitzer's "premature ejaculation and pharmaceutical company-based medicine: the dapoxetine case". | 2008 Apr |
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Safety and efficacy of dapoxetine in the treatment of premature ejaculation: a double-blind, placebo-controlled, fixed-dose, randomized study. | 2008 May |
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Emerging treatments for premature ejaculation: focus on dapoxetine. | 2009 |
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Dapoxetine for the treatment of premature ejaculation: results from a randomized, double-blind, placebo-controlled phase 3 trial in 22 countries. | 2009 Apr |
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[Premature ejaculation]. | 2009 Jun |
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Counterfeit dapoxetine sold on the Internet contains undisclosed sildenafil. | 2010 Aug |
Patents
Sample Use Guides
The recommended starting dose for all patients is 30 mg, taken as needed approximately 1 to 3 hours prior to sexual activity. If the effect of 30 mg is insufficient and the side effects are acceptable, the dose may be increased to the maximum recommended dose of 60 mg. The maximum recommended dosing frequency is one dose every 24 hours.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28058743
Effect of dapoxetine on Kv channels using freshly isolated coronary arterial smooth muscle cells was investigated. Whole-cell configuration was used to record Kv currents. Steady-state voltage-dependent inactivation curves were acquired using a two-step protocol. Peak currents were recorded with a 600-ms test potential to +40 mV after 7-s preconditioning steps (from -80 to +30 mV in steps of 10 mV) in the absence and presence of dapoxetine
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C94725
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WHO-VATC |
QG04BX14
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C265
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G04BX14
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100000083441
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119356-77-3
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Dapoxetine
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C75168
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GB2433A4M3
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CHEMBL2110900
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m4091
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DB04884
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C080598
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ACTIVE MOIETY