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
- Weight
- Average: 305.4134
Monoisotopic: 305.177964363 - Chemical Formula
- C21H23NO
- Synonyms
- Dapoxetina
- Dapoxetine
- Dapoxetinum
- External IDs
- LY 210448
- LY-210448
Pharmacology
- Indication
For the treatment of premature ejaculation.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- 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 •••••••••••• ••••••• ••••••• ••••••• ••••••• •••• •••••• - Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-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
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- 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 Turkey 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 Turkey 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 Turkey 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 Turkey 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 Turkey
Categories
- ATC Codes
- G04BX14 — Dapoxetine
- 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
- 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]
- Cirillo-Penn K, Modi NB: Dapoxetine and paroxetine for the treatment of premature ejaculation. Clin Neuropharmacol. 2007 Sep-Oct;30(5):315. [Article]
- McMahon C: Dapoxetine in the treatment of premature ejaculation. Clin Neuropharmacol. 2007 Sep-Oct;30(5):314-5. [Article]
- 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]
- 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]
- Hellstrom WJ, Heintz JW: Treatment of premature ejaculation: new drugs and treatment strategies. Curr Urol Rep. 2006 Nov;7(6):473-8. [Article]
- 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]
- 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
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 predictedDarkChem Lite v0.1.0 [M-H]- 169.70369 predictedDeepCCS 1.0 (2019) [M+H]+ 183.4400736 predictedDarkChem Lite v0.1.0 [M+H]+ 172.06168 predictedDeepCCS 1.0 (2019) [M+Na]+ 183.3432736 predictedDarkChem Lite v0.1.0 [M+Na]+ 179.17659 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- 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
- 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
- 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
- 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]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInhibitor
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- McMahon CG: Dapoxetine: a new option in the medical management of premature ejaculation. Ther Adv Urol. 2012 Oct;4(5):233-51. doi: 10.1177/1756287212453866. [Article]
- Gerotziafas GT, Mahe I, Elalamy I: New orally active anticoagulant agents for the prevention and treatment of venous thromboembolism in cancer patients. Ther Clin Risk Manag. 2014 Jun 13;10:423-36. doi: 10.2147/TCRM.S49063. eCollection 2014. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
Drug created at October 21, 2007 11:51 / Updated at June 12, 2021 10:53