U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of DAPOXETINE

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

HIDE SMILES / InChI
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

Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/9234326

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
2.68 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PRILIGY

Approved Use

INDICATIONS. 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

PubMed

TitleDatePubMed
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
Mind over matter: CNS-based approaches to urological diseases.
2004 Dec
The brain leads the way.
2004 Nov
Dapoxetine: LY 210448.
2005
The era of ESSTIs is slowly approaching?
2005 Jul
Lifelong premature ejaculation: definition, serotonergic neurotransmission and drug treatment.
2005 Jun
New agents in the treatment of premature ejaculation.
2006 Dec
Pharmacokinetic and pharmacodynamic features of dapoxetine, a novel drug for 'on-demand' treatment of premature ejaculation.
2006 Feb
Dapoxetine, a novel treatment for premature ejaculation, does not have pharmacokinetic interactions with phosphodiesterase-5 inhibitors.
2006 Jan-Feb
Just hold on a minute (or should it be two?).
2006 Jul
Treatment of premature ejaculation: new drugs and treatment strategies.
2006 Nov
Dapoxetine for treatment of premature ejaculation.
2006 Nov 11
Pharmacokinetics of dapoxetine, a new treatment for premature ejaculation: Impact of age and effects of a high-fat meal.
2006 Sep
Efficacy and tolerability of dapoxetine in treatment of premature ejaculation: an integrated analysis of two double-blind, randomised controlled trials.
2006 Sep 9
Medical therapy for premature ejaculation.
2006 Sep 9
Comparison of dapoxetine versus paroxetine in patients with premature ejaculation: a double-blind, placebo-controlled, fixed-dose, randomized study.
2006 Sep-Oct
Premature ejaculation.
2007 Apr
Effect of acute dapoxetine administration on the pudendal motoneuron reflex in anesthetized rats: comparison with paroxetine.
2007 Jan
Development of in situ ion selective sensors for dissolution.
2007 Jan 2
The majority of men with lifelong premature ejaculation prefer daily drug treatment: an observation study in a consecutive group of Dutch men.
2007 Jul
Dapoxetine, a novel selective serotonin transport inhibitor for the treatment of premature ejaculation.
2007 Jun
Selective serotonin reuptake inhibitors in the treatment of premature ejaculation.
2007 Jun 5
Dapoxetine has no pharmacokinetic or cognitive interactions with ethanol in healthy male volunteers.
2007 Mar
Regarding Waldinger and Schweitzer's "premature ejaculation and pharmaceutical company-based medicine: the dapoxetine case".
2008 Apr
Safety and efficacy of dapoxetine in the treatment of premature ejaculation: a double-blind, placebo-controlled, fixed-dose, randomized study.
2008 May
Emerging treatments for premature ejaculation: focus on dapoxetine.
2009
Dapoxetine for the treatment of premature ejaculation: results from a randomized, double-blind, placebo-controlled phase 3 trial in 22 countries.
2009 Apr
[Premature ejaculation].
2009 Jun
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
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
Name Type Language
DAPOXETINE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
DAPOXETINE [MART.]
Common Name English
Dapoxetine [WHO-DD]
Common Name English
KUTUB
Brand Name English
LY-210448
Code English
PRILIGY
Brand Name English
BENZENEMETHANAMINE, N,N-DIMETHYL-.ALPHA.-(2-(1-NAPHTHALENYLOXY)ETHYL)-
Systematic Name English
(+)-(S)-N,N-DIMETHYL-.ALPHA.-(2-(1-NAPHTHYLOXY)ETHYL)BENZYLAMINE
Systematic Name English
DAPOXETINE [MI]
Common Name English
dapoxetine [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C94725
Created by admin on Fri Dec 15 16:17:24 GMT 2023 , Edited by admin on Fri Dec 15 16:17:24 GMT 2023
WHO-VATC QG04BX14
Created by admin on Fri Dec 15 16:17:24 GMT 2023 , Edited by admin on Fri Dec 15 16:17:24 GMT 2023
NCI_THESAURUS C265
Created by admin on Fri Dec 15 16:17:24 GMT 2023 , Edited by admin on Fri Dec 15 16:17:24 GMT 2023
WHO-ATC G04BX14
Created by admin on Fri Dec 15 16:17:24 GMT 2023 , Edited by admin on Fri Dec 15 16:17:24 GMT 2023
Code System Code Type Description
SMS_ID
100000083441
Created by admin on Fri Dec 15 16:17:24 GMT 2023 , Edited by admin on Fri Dec 15 16:17:24 GMT 2023
PRIMARY
CAS
119356-77-3
Created by admin on Fri Dec 15 16:17:24 GMT 2023 , Edited by admin on Fri Dec 15 16:17:24 GMT 2023
PRIMARY
WIKIPEDIA
Dapoxetine
Created by admin on Fri Dec 15 16:17:24 GMT 2023 , Edited by admin on Fri Dec 15 16:17:24 GMT 2023
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NCI_THESAURUS
C75168
Created by admin on Fri Dec 15 16:17:24 GMT 2023 , Edited by admin on Fri Dec 15 16:17:24 GMT 2023
PRIMARY
FDA UNII
GB2433A4M3
Created by admin on Fri Dec 15 16:17:24 GMT 2023 , Edited by admin on Fri Dec 15 16:17:24 GMT 2023
PRIMARY
ChEMBL
CHEMBL2110900
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PRIMARY
EVMPD
SUB06908MIG
Created by admin on Fri Dec 15 16:17:24 GMT 2023 , Edited by admin on Fri Dec 15 16:17:24 GMT 2023
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IUPHAR
7901
Created by admin on Fri Dec 15 16:17:24 GMT 2023 , Edited by admin on Fri Dec 15 16:17:24 GMT 2023
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DRUG CENTRAL
4381
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PUBCHEM
71353
Created by admin on Fri Dec 15 16:17:24 GMT 2023 , Edited by admin on Fri Dec 15 16:17:24 GMT 2023
PRIMARY
MERCK INDEX
m4091
Created by admin on Fri Dec 15 16:17:24 GMT 2023 , Edited by admin on Fri Dec 15 16:17:24 GMT 2023
PRIMARY Merck Index
INN
6834
Created by admin on Fri Dec 15 16:17:24 GMT 2023 , Edited by admin on Fri Dec 15 16:17:24 GMT 2023
PRIMARY
EPA CompTox
DTXSID0057627
Created by admin on Fri Dec 15 16:17:24 GMT 2023 , Edited by admin on Fri Dec 15 16:17:24 GMT 2023
PRIMARY
DRUG BANK
DB04884
Created by admin on Fri Dec 15 16:17:24 GMT 2023 , Edited by admin on Fri Dec 15 16:17:24 GMT 2023
PRIMARY
MESH
C080598
Created by admin on Fri Dec 15 16:17:24 GMT 2023 , Edited by admin on Fri Dec 15 16:17:24 GMT 2023
PRIMARY