Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C21H23NO.ClH |
Molecular Weight | 341.8751 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)[C@@]([H])(CCOc1cccc2ccccc21)c3ccccc3.Cl
InChI
InChIKey=IHWDIQRWYNMKFM-BDQAORGHSA-N
InChI=1S/C21H23NO.ClH/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;1H/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 |
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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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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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Pharmacologic treatment of rapid ejaculation: levels of evidence-based review. | 2006 Sep |
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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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Selective serotonin reuptake inhibitors in the treatment of premature ejaculation. | 2007 Jun 5 |
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[Update of pharmacotherapy for premature ejaculation]. | 2007 May |
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Rational use of dapoxetine for the treatment of premature ejaculation. | 2008 Oct |
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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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The Premature Ejaculation Profile: validation of self-reported outcome measures for research and practice. | 2009 Feb |
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MMIX: annus festine lente? | 2009 Jan |
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Challenges in the pharmacotherapy of urogenital disorders. | 2010 |
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The dapoxetine paradox. | 2010 Apr |
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Counterfeit dapoxetine sold on the Internet contains undisclosed sildenafil. | 2010 Aug |
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[Dapoxetine in treatment of premature ejaculation: a systematic review]. | 2010 Aug 18 |
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Pharmacokinetics of dapoxetine hydrochloride in healthy Chinese, Japanese, and Caucasian men. | 2010 Dec |
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Premature ejaculation: treatment update. | 2010 Feb |
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Recent advances in the treatment of premature ejaculation. | 2010 Feb 18 |
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Baseline characteristics and treatment outcomes for men with acquired or lifelong premature ejaculation with mild or no erectile dysfunction: integrated analyses of two phase 3 dapoxetine trials. | 2010 Jun |
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Guidelines on male sexual dysfunction: erectile dysfunction and premature ejaculation. | 2010 May |
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
Created by
admin on Sat Jun 26 11:11:12 UTC 2021 , Edited by admin on Sat Jun 26 11:11:12 UTC 2021
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NCI_THESAURUS |
C265
Created by
admin on Sat Jun 26 11:11:12 UTC 2021 , Edited by admin on Sat Jun 26 11:11:12 UTC 2021
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Code System | Code | Type | Description | ||
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C080598
Created by
admin on Sat Jun 26 11:11:12 UTC 2021 , Edited by admin on Sat Jun 26 11:11:12 UTC 2021
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PRIMARY | |||
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M4091
Created by
admin on Sat Jun 26 11:11:12 UTC 2021 , Edited by admin on Sat Jun 26 11:11:12 UTC 2021
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PRIMARY | Merck Index | ||
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129938-20-1
Created by
admin on Sat Jun 26 11:11:12 UTC 2021 , Edited by admin on Sat Jun 26 11:11:12 UTC 2021
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PRIMARY | |||
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71352
Created by
admin on Sat Jun 26 11:11:12 UTC 2021 , Edited by admin on Sat Jun 26 11:11:12 UTC 2021
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PRIMARY | |||
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C76101
Created by
admin on Sat Jun 26 11:11:12 UTC 2021 , Edited by admin on Sat Jun 26 11:11:12 UTC 2021
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PRIMARY | |||
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SUB30408
Created by
admin on Sat Jun 26 11:11:12 UTC 2021 , Edited by admin on Sat Jun 26 11:11:12 UTC 2021
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PRIMARY | |||
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U4OHT63MRI
Created by
admin on Sat Jun 26 11:11:12 UTC 2021 , Edited by admin on Sat Jun 26 11:11:12 UTC 2021
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PRIMARY | |||
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CHEMBL2110900
Created by
admin on Sat Jun 26 11:11:12 UTC 2021 , Edited by admin on Sat Jun 26 11:11:12 UTC 2021
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PRIMARY |
ACTIVE MOIETY
SUBSTANCE RECORD