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HomeProduct name listDapoxetine hydrochloride

Dapoxetine hydrochloride

  • CAS NO.:129938-20-1
  • Empirical Formula: C21H24ClNO
  • Molecular Weight: 341.88
  • MDL number: MFCD08272809
  • EINECS: 640-411-8
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-05 08:26:49
Dapoxetine hydrochloride Structural

What is Dapoxetine hydrochloride?

Description

Dapoxetine hydrochloride, belonging to the class of SSRIs, was the first drug originally approved for the on-demand treatment of men with PE by seven European countries in 2008.
Premature ejaculation (PE) is the most common male sexual dysfunction. Dapoxetine is a short-acting SSRI. It is differentiated from the existing SSRI treatments for PE by the fact that it can be administered on an as-needed basis. In healthy subjects, dapoxetine is rapidly absorbed after oral administration with a peak plasma concentration (Tmax) occurring between 1.4 and 2h.

Chemical properties

Dapoxetine hydrochloride is a white to slightly yellow powder. It is freely soluble in methanol, propylene glycol, some organic solvents (eg. N,N-dimethylformamide) , slightly soluble in ethanol and almost insoluble in water. It is a BCSI class II compound, and poor solubility is a key factor affecting the difference in clinical efficacy. Dapoxetine hydrochloride exists in various crystal forms, the solubility of different crystal forms is quite different, and there is a phenomenon of phase and transformation between crystal forms.

Originator

Lilly (US)

The Uses of Dapoxetine hydrochloride

Dapoxetine hydrochloride is a short-acting novel selective serotonin reuptake inhibitor marketed for the treatment of premature ejaculation in men. Premature ejaculation (PE) is the most common male sexual disorder, estimated to affect up to 30% of men.

What are the applications of Application

Dapoxetine Hydrochloride is a selective serotonin reuptake inhibitor

brand name

Priligy

General Description

Dapoxetine ((+)-(S)-N,N-dimethyl-(α)-[2(1naphthal enyloxy)ethyl]-benzenemethanamine hydrochloride) possess a similar structure as that of fluoxetine.

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.

storage

room temperature (desiccate)

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.

Properties of Dapoxetine hydrochloride

Melting point: 175-1790C
alpha  D +135.78° (c = 2.18 in methanol)
storage temp.  room temp
solubility  DMSO: ≥20mg/mL
form  powder
color  white
optical activity [α]/D +125 to +135°, c = 1 in methanol
Merck  14,2821
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/t20-;/s3
CAS DataBase Reference 129938-20-1(CAS DataBase Reference)

Safety information for Dapoxetine hydrochloride

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H319:Serious eye damage/eye irritation
H413:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Dapoxetine hydrochloride

InChIKey IHWDIQRWYNMKFM-OZYVVJTJNA-N
SMILES O(C1=CC=CC2C=CC=CC1=2)CC[C@@H](C1C=CC=CC=1)N(C)C.Cl |&1:13,r|

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