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
Molecular Formula | C21H23NO |
Molecular Weight | 305.4134 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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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New agents in the treatment of premature ejaculation. | 2006 Dec |
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Just hold on a minute (or should it be two?). | 2006 Jul |
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Single- and multiple-dose pharmacokinetics of dapoxetine hydrochloride, a novel agent for the treatment of premature ejaculation. | 2006 Mar |
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What's the point? | 2006 Mar |
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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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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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Development of in situ ion selective sensors for dissolution. | 2007 Jan 2 |
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Dapoxetine has no pharmacokinetic or cognitive interactions with ethanol in healthy male volunteers. | 2007 Mar |
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Supraspinal site of action for the inhibition of ejaculatory reflex by dapoxetine. | 2007 Mar |
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W is for Wilbert's wee willy (which tends to go off prematurely). | 2007 Sep 25 |
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Dapoxetine and paroxetine for the treatment of premature ejaculation. | 2007 Sep-Oct |
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Dapoxetine in the treatment of premature ejaculation. | 2007 Sep-Oct |
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Re: François Giuliano, Donald L. Patrick, Hartmut Porst, et Al. for the 3004 study group. Premature ejaculation: results from a five-country European observational study. Eur urol 2008;53:1048-57. | 2008 Jun |
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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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Isolation and structural elucidation of dapoxetine as an adulterant in a health supplement used for sexual performance enhancement. | 2009 Dec 5 |
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MMIX: annus festine lente? | 2009 Jan |
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Pharmacokinetic, pharmacodynamic, and electrocardiographic effects of dapoxetine and moxifloxacin compared with placebo in healthy adult male subjects. | 2009 Jun |
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[Efficacy and safety of selective serotonin re-uptake inhibitors in the treatment of premature ejaculation: a systematic evaluation]. | 2009 Mar |
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Dapoxetine: a novel treatment for premature ejaculation. | 2009 Sep |
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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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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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Highly efficient, enantioselective syntheses of (S)-(+)- and (R)-(-)-dapoxetine starting with 3-phenyl-1-propanol. | 2010 Jan 1 |
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Available and future therapies for premature ejaculation. | 2010 Jul |
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Dapoxetine for premature ejaculation. | 2010 Jul |
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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
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:17:24 UTC 2023
by
admin
on
Fri Dec 15 16:17:24 UTC 2023
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Record UNII |
GB2433A4M3
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C94725
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WHO-VATC |
QG04BX14
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NCI_THESAURUS |
C265
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WHO-ATC |
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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SUB06908MIG
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7901
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4381
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71353
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m4091
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6834
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DTXSID0057627
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DB04884
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C080598
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Related Record | Type | Details | ||
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ACTIVE MOIETY |