Dapoxetine

Identification

Summary

Dapoxetine is a selective serotonin reuptake inhibitor used in the treatment of premature ejaculation.

Generic Name

Dapoxetine

DrugBank Accession Number

DB04884

Background

Dapoxetine is a selective serotonin reuptake inhibitor, for the treatment of premature ejaculation. In a phase II proof-of-concept study conducted by PPD, dapoxetine demonstrated a statistically significant increase in ejaculatory latency when compared to placebo. Alza submitted a NDA to the FDA for dapoxetine for the treatment of premature ejaculation in December 2004. In October 2005, the company received a FDA Non-Approvable letter from the FDA, at which time they planned to work with regulators to address outstanding questions.

Type

Small Molecule

Groups

Investigational

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Dapoxetine (DB04884)

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Weight

Average: 305.4134
Monoisotopic: 305.177964363

Chemical Formula

C₂₁H₂₃NO

Synonyms

• Dapoxetina
• Dapoxetine
• Dapoxetinum

External IDs

• LY 210448
• LY-210448

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Pharmacology

Indication

For the treatment of premature ejaculation.

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Treatment of	Premature ejaculation		••••••••••••	•••••	••••••••	••••••
Used in combination to treat	Premature ejaculation	Combination Product in combination with: Tadalafil (DB00820)	••••••••••••		•••••••• •••••••••••	••••••• ••••••
Treatment of	Premature ejaculation		••••••••••••			••••••• ••••••• ••••••• ••••••• •••• ••••••

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Pharmacodynamics

Dapoxetine is a selective serotonin reuptake inhibitor currently undergoing trials through Alza (under license from GenuPro, a collaboration between Eli Lilly and PPD). Dapoxetine is a short-acting SSRI drug currently being considered for approval by the Food and Drug Administration (FDA) for the treatment of premature ejaculation in men, which would make it the first drug approved for such treatment. Despite two clinical trials finished in 2006, experts doubt it will be approved by the FDA soon because SSRIs come with undesirable side-effects after long-term use, such as psychiatric problems, dermatological reactions, increase in body weight, lower sex-drive, nausea, headache, upset stomach and weakness, thus not significantly outweighing the benefit of premature ejaculation medication versus the risks. By contrast with SSRIs approved for depression, which take 2 weeks or longer to reach steady-state concentration, dapoxetine has a unique pharmacokinetic profile, with a short time to maximum serum concentration (about 1 h) and rapid elimination (initial half-life of 1-2 h).

Mechanism of action

The drug's mechanism of action is thought to be related to inhibition of neuronal reuptake of serotonin and subsequent potentiation of serotonin activity. The central ejaculatory neural circuit comprises spinal and cerebral areas that form a highly interconnected network. The sympathetic, parasympathetic, and somatic spinal centers, under the influence of sensory genital and cerebral stimuli integrated and processed at the spinal cord level, act in synergy to command physiologic events occurring during ejaculation. Experimental evidence indicates that serotonin (5-HT), throughout brain descending pathways, exerts an inhibitory role on ejaculation. To date, three 5-HT receptor subtypes (5-HT(1A), 5-HT(1B), and 5-HT(2C)) have been postulated to mediate 5-HT's modulating activity on ejaculation.

Target	Actions	Organism
U5-hydroxytryptamine receptor 1A	Not Available	Humans
U5-hydroxytryptamine receptor 1B	Not Available	Humans
U5-hydroxytryptamine receptor 2C	Not Available	Humans

Absorption

Rapidly absorbed.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half-life

Initial half-life of 1-2 hours.

Clearance

Not Available

Adverse Effects

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Toxicity

Not Available

Pathways

Not Available

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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1,2-Benzodiazepine	The risk or severity of adverse effects can be increased when 1,2-Benzodiazepine is combined with Dapoxetine.
Abametapir	The serum concentration of Dapoxetine can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Dapoxetine can be increased when combined with Abatacept.
Abciximab	The risk or severity of hemorrhage can be increased when Dapoxetine is combined with Abciximab.
Abemaciclib	The metabolism of Abemaciclib can be decreased when combined with Dapoxetine.

Food Interactions

Not Available

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Dapoxetine hydrochloride	U4OHT63MRI	129938-20-1	IHWDIQRWYNMKFM-BDQAORGHSA-N

International/Other Brands

Priligy

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
DAPOKSEL 30 MG/50 MG FILM TABLET ,3 FILM TABLET	Dapoxetine hydrochloride (30 mg) + Sildenafil citrate (50 mg)	Tablet, film coated	Oral	NOBEL İLAÇ SAN. VE TİC. A.Ş.	2016-05-24	2017-11-14
DAPOKSEL 30 MG/50 MG FILM TABLET ,6 FILM TABLET	Dapoxetine hydrochloride (30 mg) + Sildenafil citrate (50 mg)	Tablet, film coated	Oral	NOBEL İLAÇ SAN. VE TİC. A.Ş.	2016-05-24	2017-11-14
DAPOXIL 30/50 MG FILM KAPLI TABLET, 3 FILM KAPLI TABLET	Dapoxetine hydrochloride (30 mg) + Sildenafil citrate (50 mg)	Tablet, coated	Oral	VİTALİS İLAÇ SAN. TİC. A.Ş.	2020-08-14	2021-02-15
DAPOXIL 30/50 MG FILM KAPLI TABLET, 6 FILM KAPLI TABLET	Dapoxetine hydrochloride (30 mg) + Sildenafil citrate (50 mg)	Tablet, coated	Oral	VİTALİS İLAÇ SAN. TİC. A.Ş.	2020-08-14	2021-02-15
DAPOXIL 30/50 MG FILM KAPLI TABLET,18 FILM KAPLI TABLET	Dapoxetine hydrochloride (30 mg) + Sildenafil citrate (50 mg)	Tablet, coated	Oral	VİTALİS İLAÇ SAN. TİC. A.Ş.	2020-08-14	2021-02-15

Categories

ATC Codes

G04BX14 — Dapoxetine

• G04BX — Other urologicals
• G04B — UROLOGICALS
• G04 — UROLOGICALS
• G — GENITO URINARY SYSTEM AND SEX HORMONES

Drug Categories

• Amines
• Antidepressive Agents
• Benzene Derivatives
• Benzyl Compounds
• Central Nervous System Depressants
• Cytochrome P-450 CYP2D6 Substrates
• Cytochrome P-450 CYP3A Inhibitors
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A4 Inhibitors
• Cytochrome P-450 CYP3A4 Inhibitors (weak)
• Cytochrome P-450 CYP3A4 Substrates
• Cytochrome P-450 Enzyme Inhibitors
• Cytochrome P-450 Substrates
• Genito Urinary System and Sex Hormones
• Hypoglycemia-Associated Agents
• Selective Serotonin Reuptake Inhibitors
• Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
• Serotonin Agents
• Serotonin Modulators
• Urologicals

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Not Available

Direct Parent

Naphthalenes

Alternative Parents

Aralkylamines / Alkyl aryl ethers / Benzene and substituted derivatives / Trialkylamines / Organopnictogen compounds / Hydrocarbon derivatives

Substituents

Alkyl aryl ether / Amine / Aralkylamine / Aromatic homopolycyclic compound / Ether / Hydrocarbon derivative / Monocyclic benzene moiety / Naphthalene / Organic nitrogen compound / Organic oxygen compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Affected organisms

• Humans and other mammals

Chemical Identifiers

UNII

GB2433A4M3

CAS number

119356-77-3

InChI Key

USRHYDPUVLEVMC-FQEVSTJZSA-N

InChI

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

IUPAC Name

dimethyl[(1S)-3-(naphthalen-1-yloxy)-1-phenylpropyl]amine

SMILES

CN(C)[C@@H](CCOC1=CC=CC2=CC=CC=C12)C1=CC=CC=C1

References

General References

1. Safarinejad MR: Safety and efficacy of dapoxetine in the treatment of premature ejaculation: a double-blind, placebo-controlled, fixed-dose, randomized study. Neuropsychopharmacology. 2008 May;33(6):1259-65. Epub 2007 Jul 11. [Article]
2. Cirillo-Penn K, Modi NB: Dapoxetine and paroxetine for the treatment of premature ejaculation. Clin Neuropharmacol. 2007 Sep-Oct;30(5):315. [Article]
3. McMahon C: Dapoxetine in the treatment of premature ejaculation. Clin Neuropharmacol. 2007 Sep-Oct;30(5):314-5. [Article]
4. Wang WF, Chang L, Minhas S, Ralph DJ: Selective serotonin reuptake inhibitors in the treatment of premature ejaculation. Chin Med J (Engl). 2007 Jun 5;120(11):1000-6. [Article]
5. Pryor JL, Althof SE, Steidle C, Rosen RC, Hellstrom WJ, Shabsigh R, Miloslavsky M, Kell S: Efficacy and tolerability of dapoxetine in treatment of premature ejaculation: an integrated analysis of two double-blind, randomised controlled trials. Lancet. 2006 Sep 9;368(9539):929-37. [Article]
6. Hellstrom WJ, Heintz JW: Treatment of premature ejaculation: new drugs and treatment strategies. Curr Urol Rep. 2006 Nov;7(6):473-8. [Article]
7. Modi NB, Dresser M, Desai D, Edgar C, Wesnes K: Dapoxetine has no pharmacokinetic or cognitive interactions with ethanol in healthy male volunteers. J Clin Pharmacol. 2007 Mar;47(3):315-22. [Article]
8. Payne RE, Sadovsky R: Identifying and treating premature ejaculation: importance of the sexual history. Cleve Clin J Med. 2007 May;74 Suppl 3:S47-53. [Article]

External Links

KEGG Drug

D03649

PubChem Compound

71353

PubChem Substance

175426887

ChemSpider

64453

ChEBI

135962

ChEMBL

CHEMBL2110900

ZINC

ZINC000001482019

PharmGKB

PA166151992

Wikipedia

Dapoxetine

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Treatment	Erectile Dysfunction / Premature Ejaculation	1
4	Not Yet Recruiting	Treatment	Erectile Dysfunction / Premature Ejaculation / Safety Issues	1
3	Completed	Treatment	Ejaculation	2
3	Completed	Treatment	Ejaculation / Erectile Dysfunction / Sexual Dysfunctions	1
3	Completed	Treatment	Ejaculation / Sexual Dysfunctions	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Tablet, coated	Oral
Tablet, film coated	Oral
Tablet, coated	Oral
Tablet	Oral	67.200 mg
Tablet	Oral	30.000 mg
Tablet, film coated	Oral
Tablet, coated	Oral	60 mg
Tablet, film coated	Oral	30 mg
Tablet, film coated	Oral	60 mg
Tablet, coated
Tablet	Oral	30 mg
Tablet, coated	Oral	30 mg

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.000837 mg/mL	ALOGPS
logP	4.75	ALOGPS
logP	4.67	Chemaxon
logS	-5.6	ALOGPS
pKa (Strongest Basic)	8.96	Chemaxon
Physiological Charge	1	Chemaxon
Hydrogen Acceptor Count	2	Chemaxon
Hydrogen Donor Count	0	Chemaxon
Polar Surface Area	12.47 Å2	Chemaxon
Rotatable Bond Count	6	Chemaxon
Refractivity	96.14 m3·mol-1	Chemaxon
Polarizability	35 Å3	Chemaxon
Number of Rings	3	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	Yes	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9933
Blood Brain Barrier	+	0.9758
Caco-2 permeable	+	0.817
P-glycoprotein substrate	Substrate	0.5085
P-glycoprotein inhibitor I	Inhibitor	0.6464
P-glycoprotein inhibitor II	Non-inhibitor	0.8833
Renal organic cation transporter	Inhibitor	0.74
CYP450 2C9 substrate	Non-substrate	0.7484
CYP450 2D6 substrate	Substrate	0.7615
CYP450 3A4 substrate	Substrate	0.7727
CYP450 1A2 substrate	Inhibitor	0.9354
CYP450 2C9 inhibitor	Non-inhibitor	0.7353
CYP450 2D6 inhibitor	Non-inhibitor	0.5597
CYP450 2C19 inhibitor	Non-inhibitor	0.7689
CYP450 3A4 inhibitor	Non-inhibitor	0.8382
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.6419
Ames test	AMES toxic	0.6626
Carcinogenicity	Non-carcinogens	0.8718
Biodegradation	Not ready biodegradable	0.9866
Rat acute toxicity	2.5199 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.6032
hERG inhibition (predictor II)	Inhibitor	0.663

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4i-2928000000-3ad18db198c1606bc98c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0f8a-0901000000-4a9b087ffc9a6a06e2c0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0006-2900000000-fd487422bc6713fd635d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-00xs-7901000000-ae95ca17cc256300121c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-002f-1900000000-cf8fc2a0900b24eaf837
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-014l-3900000000-3a8556fe61d650451f4d
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	182.1351736	predicted	DarkChem Lite v0.1.0
[M-H]-	169.70369	predicted	DeepCCS 1.0 (2019)
[M+H]+	183.4400736	predicted	DarkChem Lite v0.1.0
[M+H]+	172.06168	predicted	DeepCCS 1.0 (2019)
[M+Na]+	183.3432736	predicted	DarkChem Lite v0.1.0
[M+Na]+	179.17659	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. 5-hydroxytryptamine receptor 1A

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

General Function

Serotonin receptor activity

Specific Function

G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...

Gene Name

HTR1A

Uniprot ID

P08908

Uniprot Name

5-hydroxytryptamine receptor 1A

Molecular Weight

46106.335 Da

Details2. 5-hydroxytryptamine receptor 1B

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

General Function

Serotonin receptor activity

Specific Function

G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive subst...

Gene Name

HTR1B

Uniprot ID

P28222

Uniprot Name

5-hydroxytryptamine receptor 1B

Molecular Weight

43567.535 Da

Details3. 5-hydroxytryptamine receptor 2C

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

General Function

Serotonin receptor activity

Specific Function

G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-...

Gene Name

HTR2C

Uniprot ID

P28335

Uniprot Name

5-hydroxytryptamine receptor 2C

Molecular Weight

51820.705 Da

References

1. Wang WF, Chang L, Minhas S, Ralph DJ: Selective serotonin reuptake inhibitors in the treatment of premature ejaculation. Chin Med J (Engl). 2007 Jun 5;120(11):1000-6. [Article]

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Drug created at October 21, 2007 11:51 / Updated at June 12, 2021 10:53