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

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
Structure of DAPOXETINE HYDROCHLORIDE

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

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
Disposition of 14C-dapoxetine in rats: complementary experiments with whole-body autoradiographic and tissue dissection techniques.
1994 Mar
Dapoxetine for treatment of premature ejaculation.
2006 Nov 11
Selective serotonin reuptake inhibitors in the treatment of premature ejaculation.
2007 Jun 5
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
Safety and efficacy of dapoxetine in the treatment of premature ejaculation: a double-blind, placebo-controlled, fixed-dose, randomized study.
2008 May
Rational use of dapoxetine for the treatment of premature ejaculation.
2008 Oct
Emerging treatments for premature ejaculation: focus on dapoxetine.
2009
Isolation and structural elucidation of dapoxetine as an adulterant in a health supplement used for sexual performance enhancement.
2009 Dec 5
[Premature ejaculation].
2009 Jun
Counterfeit dapoxetine sold on the Internet contains undisclosed sildenafil.
2010 Aug
Dapoxetine. Premature ejaculation: not worth the risk.
2010 Feb
Available and future therapies for premature ejaculation.
2010 Jul
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
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
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 Hydrochloride [WHO-DD]
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
Classification Tree Code System Code
NCI_THESAURUS C94725
Created by admin on Fri Dec 15 15:30:14 GMT 2023 , Edited by admin on Fri Dec 15 15:30:14 GMT 2023
NCI_THESAURUS C265
Created by admin on Fri Dec 15 15:30:14 GMT 2023 , Edited by admin on Fri Dec 15 15:30:14 GMT 2023
Code System Code Type Description
MESH
C080598
Created by admin on Fri Dec 15 15:30:14 GMT 2023 , Edited by admin on Fri Dec 15 15:30:14 GMT 2023
PRIMARY
MERCK INDEX
m4091
Created by admin on Fri Dec 15 15:30:14 GMT 2023 , Edited by admin on Fri Dec 15 15:30:14 GMT 2023
PRIMARY Merck Index
CAS
129938-20-1
Created by admin on Fri Dec 15 15:30:14 GMT 2023 , Edited by admin on Fri Dec 15 15:30:14 GMT 2023
PRIMARY
USAN
DD-11
Created by admin on Fri Dec 15 15:30:14 GMT 2023 , Edited by admin on Fri Dec 15 15:30:14 GMT 2023
PRIMARY
EPA CompTox
DTXSID20926531
Created by admin on Fri Dec 15 15:30:14 GMT 2023 , Edited by admin on Fri Dec 15 15:30:14 GMT 2023
PRIMARY
PUBCHEM
71352
Created by admin on Fri Dec 15 15:30:14 GMT 2023 , Edited by admin on Fri Dec 15 15:30:14 GMT 2023
PRIMARY
NCI_THESAURUS
C76101
Created by admin on Fri Dec 15 15:30:14 GMT 2023 , Edited by admin on Fri Dec 15 15:30:14 GMT 2023
PRIMARY
EVMPD
SUB30408
Created by admin on Fri Dec 15 15:30:14 GMT 2023 , Edited by admin on Fri Dec 15 15:30:14 GMT 2023
PRIMARY
SMS_ID
100000093369
Created by admin on Fri Dec 15 15:30:14 GMT 2023 , Edited by admin on Fri Dec 15 15:30:14 GMT 2023
PRIMARY
FDA UNII
U4OHT63MRI
Created by admin on Fri Dec 15 15:30:14 GMT 2023 , Edited by admin on Fri Dec 15 15:30:14 GMT 2023
PRIMARY
ChEMBL
CHEMBL2110900
Created by admin on Fri Dec 15 15:30:14 GMT 2023 , Edited by admin on Fri Dec 15 15:30:14 GMT 2023
PRIMARY