Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C21H23NO.ClH |
Molecular Weight | 341.874 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CN(C)[C@@H](CCOC1=CC=CC2=CC=CC=C12)C3=CC=CC=C3
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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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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Disposition of 14C-dapoxetine in rats: complementary experiments with whole-body autoradiographic and tissue dissection techniques. | 1994 Mar |
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Dapoxetine for treatment of premature ejaculation. | 2006 Nov 11 |
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Selective serotonin reuptake inhibitors in the treatment of premature ejaculation. | 2007 Jun 5 |
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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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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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Rational use of dapoxetine for the treatment of premature ejaculation. | 2008 Oct |
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Emerging treatments for premature ejaculation: focus on dapoxetine. | 2009 |
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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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[Premature ejaculation]. | 2009 Jun |
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Counterfeit dapoxetine sold on the Internet contains undisclosed sildenafil. | 2010 Aug |
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Dapoxetine. Premature ejaculation: not worth the risk. | 2010 Feb |
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Available and future therapies for premature ejaculation. | 2010 Jul |
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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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Validity of the patient-reported Clinical Global Impression of Change as a measure of treatment response in men with premature ejaculation. | 2010 Jun |
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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NCI_THESAURUS |
C265
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C080598
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m4091
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129938-20-1
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DD-11
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DTXSID20926531
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71352
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C76101
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SUB30408
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100000093369
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U4OHT63MRI
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CHEMBL2110900
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ACTIVE MOIETY
SUBSTANCE RECORD