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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
Structure of DAPOXETINE HYDROCHLORIDE

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

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
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
Pharmacologic treatment of rapid ejaculation: levels of evidence-based review.
2006 Sep
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
Selective serotonin reuptake inhibitors in the treatment of premature ejaculation.
2007 Jun 5
[Update of pharmacotherapy for premature ejaculation].
2007 May
Rational use of dapoxetine for the treatment of premature ejaculation.
2008 Oct
Dapoxetine for the treatment of premature ejaculation: results from a randomized, double-blind, placebo-controlled phase 3 trial in 22 countries.
2009 Apr
The Premature Ejaculation Profile: validation of self-reported outcome measures for research and practice.
2009 Feb
MMIX: annus festine lente?
2009 Jan
Challenges in the pharmacotherapy of urogenital disorders.
2010
The dapoxetine paradox.
2010 Apr
Counterfeit dapoxetine sold on the Internet contains undisclosed sildenafil.
2010 Aug
[Dapoxetine in treatment of premature ejaculation: a systematic review].
2010 Aug 18
Pharmacokinetics of dapoxetine hydrochloride in healthy Chinese, Japanese, and Caucasian men.
2010 Dec
Premature ejaculation: treatment update.
2010 Feb
Recent advances in the treatment of premature ejaculation.
2010 Feb 18
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
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
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 HYDROCHLORIDE
MART.   MI   USAN   WHO-DD  
USAN  
Official Name English
DAPOXETINE HYDROCHLORIDE [MI]
Common Name English
LY210448 HCL
Code English
(+)-(S)-N,N-DIMETHYL-.ALPHA.-(2-(1-NAPHTHYLOXY)ETHYL)BENZYLAMINE HYDROCHLORIDE
Systematic Name English
DAPOXETINE HYDROCHLORIDE [USAN]
Common Name English
DAPOXETINE HCL
Common Name English
DAPOXETINE HYDROCHLORIDE [MART.]
Common Name English
BENZENEMETHANAMINE, N,N-DIMETHYL-.ALPHA.-(2-(1-NAPHTHALENYLOXY)ETHYL)-, HYDROCHLORIDE, (S)-
Systematic Name English
DAPOXETINE (AS HYDROCHLORIDE)
Common Name English
DAPOXETINE HYDROCHLORIDE [WHO-DD]
Common Name English
Classification Tree Code System Code
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
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
Code System Code Type Description
MESH
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
PRIMARY
MERCK INDEX
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
PRIMARY Merck Index
CAS
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
PRIMARY
PUBCHEM
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
PRIMARY
NCI_THESAURUS
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
PRIMARY
EVMPD
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
PRIMARY
FDA UNII
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
PRIMARY
ChEMBL
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
PRIMARY