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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

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

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
New agents in the treatment of premature ejaculation.
2006 Dec
Just hold on a minute (or should it be two?).
2006 Jul
Single- and multiple-dose pharmacokinetics of dapoxetine hydrochloride, a novel agent for the treatment of premature ejaculation.
2006 Mar
What's the point?
2006 Mar
Pharmacokinetics of dapoxetine, a new treatment for premature ejaculation: Impact of age and effects of a high-fat meal.
2006 Sep
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
Development of in situ ion selective sensors for dissolution.
2007 Jan 2
Dapoxetine has no pharmacokinetic or cognitive interactions with ethanol in healthy male volunteers.
2007 Mar
Supraspinal site of action for the inhibition of ejaculatory reflex by dapoxetine.
2007 Mar
W is for Wilbert's wee willy (which tends to go off prematurely).
2007 Sep 25
Dapoxetine and paroxetine for the treatment of premature ejaculation.
2007 Sep-Oct
Dapoxetine in the treatment of premature ejaculation.
2007 Sep-Oct
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
Dapoxetine for the treatment of premature ejaculation: results from a randomized, double-blind, placebo-controlled phase 3 trial in 22 countries.
2009 Apr
Isolation and structural elucidation of dapoxetine as an adulterant in a health supplement used for sexual performance enhancement.
2009 Dec 5
MMIX: annus festine lente?
2009 Jan
Pharmacokinetic, pharmacodynamic, and electrocardiographic effects of dapoxetine and moxifloxacin compared with placebo in healthy adult male subjects.
2009 Jun
[Efficacy and safety of selective serotonin re-uptake inhibitors in the treatment of premature ejaculation: a systematic evaluation].
2009 Mar
Dapoxetine: a novel treatment for premature ejaculation.
2009 Sep
Challenges in the pharmacotherapy of urogenital disorders.
2010
The dapoxetine paradox.
2010 Apr
Pharmacokinetics of dapoxetine hydrochloride in healthy Chinese, Japanese, and Caucasian men.
2010 Dec
Premature ejaculation: treatment update.
2010 Feb
Highly efficient, enantioselective syntheses of (S)-(+)- and (R)-(-)-dapoxetine starting with 3-phenyl-1-propanol.
2010 Jan 1
Available and future therapies for premature ejaculation.
2010 Jul
Dapoxetine for premature ejaculation.
2010 Jul
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:17:24 UTC 2023
Edited
by admin
on Fri Dec 15 16:17:24 UTC 2023
Record UNII
GB2433A4M3
Record Status Validated (UNII)
Record Version
  • Download
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 UTC 2023 , Edited by admin on Fri Dec 15 16:17:24 UTC 2023
WHO-VATC QG04BX14
Created by admin on Fri Dec 15 16:17:24 UTC 2023 , Edited by admin on Fri Dec 15 16:17:24 UTC 2023
NCI_THESAURUS C265
Created by admin on Fri Dec 15 16:17:24 UTC 2023 , Edited by admin on Fri Dec 15 16:17:24 UTC 2023
WHO-ATC G04BX14
Created by admin on Fri Dec 15 16:17:24 UTC 2023 , Edited by admin on Fri Dec 15 16:17:24 UTC 2023
Code System Code Type Description
SMS_ID
100000083441
Created by admin on Fri Dec 15 16:17:24 UTC 2023 , Edited by admin on Fri Dec 15 16:17:24 UTC 2023
PRIMARY
CAS
119356-77-3
Created by admin on Fri Dec 15 16:17:24 UTC 2023 , Edited by admin on Fri Dec 15 16:17:24 UTC 2023
PRIMARY
WIKIPEDIA
Dapoxetine
Created by admin on Fri Dec 15 16:17:24 UTC 2023 , Edited by admin on Fri Dec 15 16:17:24 UTC 2023
PRIMARY
NCI_THESAURUS
C75168
Created by admin on Fri Dec 15 16:17:24 UTC 2023 , Edited by admin on Fri Dec 15 16:17:24 UTC 2023
PRIMARY
FDA UNII
GB2433A4M3
Created by admin on Fri Dec 15 16:17:24 UTC 2023 , Edited by admin on Fri Dec 15 16:17:24 UTC 2023
PRIMARY
ChEMBL
CHEMBL2110900
Created by admin on Fri Dec 15 16:17:24 UTC 2023 , Edited by admin on Fri Dec 15 16:17:24 UTC 2023
PRIMARY
EVMPD
SUB06908MIG
Created by admin on Fri Dec 15 16:17:24 UTC 2023 , Edited by admin on Fri Dec 15 16:17:24 UTC 2023
PRIMARY
IUPHAR
7901
Created by admin on Fri Dec 15 16:17:24 UTC 2023 , Edited by admin on Fri Dec 15 16:17:24 UTC 2023
PRIMARY
DRUG CENTRAL
4381
Created by admin on Fri Dec 15 16:17:24 UTC 2023 , Edited by admin on Fri Dec 15 16:17:24 UTC 2023
PRIMARY
PUBCHEM
71353
Created by admin on Fri Dec 15 16:17:24 UTC 2023 , Edited by admin on Fri Dec 15 16:17:24 UTC 2023
PRIMARY
MERCK INDEX
m4091
Created by admin on Fri Dec 15 16:17:24 UTC 2023 , Edited by admin on Fri Dec 15 16:17:24 UTC 2023
PRIMARY Merck Index
INN
6834
Created by admin on Fri Dec 15 16:17:24 UTC 2023 , Edited by admin on Fri Dec 15 16:17:24 UTC 2023
PRIMARY
EPA CompTox
DTXSID0057627
Created by admin on Fri Dec 15 16:17:24 UTC 2023 , Edited by admin on Fri Dec 15 16:17:24 UTC 2023
PRIMARY
DRUG BANK
DB04884
Created by admin on Fri Dec 15 16:17:24 UTC 2023 , Edited by admin on Fri Dec 15 16:17:24 UTC 2023
PRIMARY
MESH
C080598
Created by admin on Fri Dec 15 16:17:24 UTC 2023 , Edited by admin on Fri Dec 15 16:17:24 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY