129938-20-1

Basic information

• Product Name: Dapoxetine hydrochloride
• Synonyms: DL-Dapoxteine HCL;N,N-DiMethyl-1-phenyl-3-(1-naphthalenyloxy)propanaMinehydrochloride;(S)-N,N-Dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine hydrochloride;D-(+)N,N-diMethyl-3-(naphthalen-1-yloxy);(αS)- N,N-dimethyl-α-[2-(1-naphthalenyloxy)ethyl]-benzenemethanamine, hydrochloride (1:1);(6R,7R)-7-Amino-8-oxo-3-(1-propenyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidDapoxetine hydrochloride;Dapoxetine hydrochloride (1S)-N,N-Dimethyl-3-naphthalen-1-yloxy-1-phenyl-propan-1-amine hydrochloride;S-(+)-N,N-dimethyl-a-[2-(naphthalenyloxy)ethyl] benzenemethanamine hydrochloride, LY-210448 hydrochloride
• CAS NO: 129938-20-1
• Molecular Formula: C9H7ClN2O5
• Molecular Weight: 258.62
• EINECS: 1308068-626-2
• Product Categories: Dapoxetine Hydrochloride;Intermediates & Fine Chemicals;Pharmaceuticals;Amines;Aromatics;Inhibitors
• Mol File: 129938-20-1.mol
• Article Data: 0

Chemical Properties

• Melting Point: 175-1790C
• Boiling Point: 454.4 °C at 760 mmHg
• Flash Point: 132.6 °C
• Appearance: white/
• Vapor Pressure: 1.27E-09mmHg at 25°C
• Storage Temp.: -20°C Freezer
• Solubility: DMSO: ≥20mg/mL
• Merck: 14,2821
• CAS DataBase Reference: Dapoxetine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Dapoxetine hydrochloride(129938-20-1)
• EPA Substance Registry System: Dapoxetine hydrochloride(129938-20-1)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-36-50/53
• Safety Statements: 36-60-61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 129938-20-1(Hazardous Substances Data)

Usage

Description

Dapoxetine hydrochloride, also known as Priligy, is a short-acting selective serotonin reuptake inhibitor (SSRI) with a unique structure similar to fluoxetine. It is the first drug approved for the on-demand treatment of premature ejaculation (PE) in men, offering a rapid absorption and peak plasma concentration within 1.4 to 2 hours after oral administration. As a BCSI class II compound, its solubility varies with different crystal forms, affecting clinical efficacy.

Uses

Used in Pharmaceutical Industry:
Dapoxetine hydrochloride is used as a therapeutic agent for the treatment of premature ejaculation (PE) in men. It is particularly effective due to its rapid absorption and short-acting nature, providing on-demand relief for the most common male sexual dysfunction, which is estimated to affect up to 30% of men.

Originator

Lilly (US)

Biochem/physiol Actions

Potent Selective serotonin reuptake inhibitor (SSRI); used in treatment of premature ejaculation

Synthesis

Dapoxetine can be synthesized in four chemical steps starting from R-1phenyl- 1,3-propanediol via selective tosylation of the primary hydroxy group with p-toluenesulfonyl chloride, triethylamine and 4-(dimethylamino) pyridine (DMAP), and subsequent condensation with 1naphthol by means of sodium- or lithium hydroxide to yield R-3-(1naphthyloxy)- 1-phenylpropanol as the key intermediate. Conversion of the alcohol group to the corresponding mesylate with methanesulfonyl chloride, triethylamine, and DMAP, followed by treatment with dimethylamine affords dapoxetine, which is then acidified to its hydrochloride salt.

Mode of action

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. Dapoxetine is a centrally-acting SSRI that modulates serotonin levels in relevant areas such as the lateral paragigantocellular nucleus through inhibition of the serotonin transporter (SERT). This compound also decreases peak amplitude and accelerates the decay rate of current inactivation in a variety of voltage-gated K+ channels.

InChI:InChI=1/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