Dapoxetine

Dapoxetine
Clinical data
Trade names	EJ-30, Priligy, others (see below)
AHFS/Drugs.com	International Drug Names
Routes of; administration	By mouth
ATC code	G04BX14 (WHO) ;
Legal status
Legal status	BR: Class C1 (Other controlled substances); In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	15–76% (mean 42%), ; Tmax = 1–1.3 hours
Protein binding	>99%
Metabolism	Liver (CYP2D6, CYP3A4), kidney (FMO1)
Metabolites	Dapoxetine-N-oxide, desmethyldapoxetine, didesmethyldapoxetine
Elimination half-life	1.5–1.6 hours
Excretion	Kidneys
Identifiers
	IUPAC name (S)-N,N-Dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine;
CAS Number	119356-77-3 ; 129938-20-1 (HCl salt);
PubChem CID	71353;
IUPHAR/BPS	7901;
ChemSpider	64453;
UNII	GB2433A4M3;
KEGG	D03649;
ChEMBL	ChEMBL2106574;
CompTox Dashboard (EPA)	DTXSID0057627 ;
Chemical and physical data
Formula	C21H23NO
Molar mass	305.421 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN(C)[C@@H](CCOc1cccc2ccccc12)c1ccccc1;
	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; Key:USRHYDPUVLEVMC-FQEVSTJZSA-N;

Dapoxetine, sold under the brand name Priligy among others, is a selective serotonin reuptake inhibitor (SSRI) used for the treatment of premature ejaculation (PE) in men ages 18 to 64 years old.^[3]^[4]^[5] Dapoxetine works by inhibiting the serotonin transporter, increasing serotonin's action at the postsynaptic cleft, and as a consequence promoting ejaculatory delay.^[6] As a member of the SSRI family, dapoxetine was initially created as an antidepressant. However, unlike other SSRIs, dapoxetine is absorbed and eliminated rapidly in the body. Its fast-acting property makes it suitable for the treatment of PE, but not as an antidepressant.^[7]

Originally created by Eli Lilly pharmaceutical company, dapoxetine was sold to Johnson & Johnson in 2003 and submitted as a New Drug Application to the US Food and Drug Administration (FDA) for the treatment of PE in 2004.^[8] Dapoxetine is sold in several European and Asian countries, and in Mexico. In the US, dapoxetine has been in phase III development. In May 2012, US-based Furiex Pharmaceuticals reached an agreement with ALZA Corp and Janssen Pharmaceuticals to market dapoxetine in the United States, Japan, and Canada, while selling the rights to market the drug in Europe, most of Asia, Africa, Latin America, and the Middle East to Menarini.^[9]

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ "Priligy (dapoxetine) Film-coated Tablets, for Oral Use. Full Prescribing Information". Russian State Register of Medicines. (in Russian). 25 July 2013. Retrieved 11 August 2016.
^ Dresser MJ, Desai D, Gidwani S, Seftel AD, Modi NB (2006). "Dapoxetine, a novel treatment for premature ejaculation, does not have pharmacokinetic interactions with phosphodiesterase-5 inhibitors". International Journal of Impotence Research. 18 (1): 104–110. doi:10.1038/Sj.Ijir.3901420. PMID 16307008.
^ McMahon CG (October 2012). "Dapoxetine: a new option in the medical management of premature ejaculation". Therapeutic Advances in Urology. 4 (5): 233–251. doi:10.1177/1756287212453866. PMC 3441133. PMID 23024705.
^ "Priligy is used to Treat Premature Ejaculation". deutschemedz.de (in German). 10 August 2015. Retrieved 19 November 2018.
^ "Australian Public Assessment Report for Dapoxetine" (PDF). Therapeutics Goods Administration. Australian Government. 2010.
^ Andersson KE, Mulhall JP, Wyllie MG (February 2006). "Pharmacokinetic and pharmacodynamic features of dapoxetine, a novel drug for 'on-demand' treatment of premature ejaculation". BJU International. 97 (2): 311–315. doi:10.1111/J.1464-410x.2006.05911.X. PMID 16430636. S2CID 34969671.
^ McCarty E, Dinsmore W (2012). "Dapoxetine: an evidence-based review of its effectiveness in treatment of premature ejaculation". Core Evidence. 7: 1–14. doi:10.2147/CE.S13841. PMC 3273363. PMID 22315582.
^ "Furiex Pharma gets rights to Priligy, some of which it sells on to Menarini". The Pharma Letter. 15 May 2012. Retrieved 11 February 2020.

[1] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[2] "Priligy (dapoxetine) Film-coated Tablets, for Oral Use. Full Prescribing Information". Russian State Register of Medicines. (in Russian). 25 July 2013. Retrieved 11 August 2016.

[Dresser-3] Dresser MJ, Desai D, Gidwani S, Seftel AD, Modi NB (2006). "Dapoxetine, a novel treatment for premature ejaculation, does not have pharmacokinetic interactions with phosphodiesterase-5 inhibitors". International Journal of Impotence Research. 18 (1): 104–110. doi:10.1038/Sj.Ijir.3901420. PMID 16307008.

[4] McMahon CG (October 2012). "Dapoxetine: a new option in the medical management of premature ejaculation". Therapeutic Advances in Urology. 4 (5): 233–251. doi:10.1177/1756287212453866. PMC 3441133. PMID 23024705.

[5] "Priligy is used to Treat Premature Ejaculation". deutschemedz.de (in German). 10 August 2015. Retrieved 19 November 2018.

[Government-6] "Australian Public Assessment Report for Dapoxetine" (PDF). Therapeutics Goods Administration. Australian Government. 2010.

[Andersson-7] Andersson KE, Mulhall JP, Wyllie MG (February 2006). "Pharmacokinetic and pharmacodynamic features of dapoxetine, a novel drug for 'on-demand' treatment of premature ejaculation". BJU International. 97 (2): 311–315. doi:10.1111/J.1464-410x.2006.05911.X. PMID 16430636. S2CID 34969671.

[8] McCarty E, Dinsmore W (2012). "Dapoxetine: an evidence-based review of its effectiveness in treatment of premature ejaculation". Core Evidence. 7: 1–14. doi:10.2147/CE.S13841. PMC 3273363. PMID 22315582.

[9] "Furiex Pharma gets rights to Priligy, some of which it sells on to Menarini". The Pharma Letter. 15 May 2012. Retrieved 11 February 2020.

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Dapoxetine

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