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Dapoxetine

Dapoxetine structure

CAS No:
119356-77-3
Formula:
C21H23NO
Chemical Name:
Dapoxetine
Synonyms:
Benzenemethanamine,N,N-dimethyl-α-[2-(1-naphthalenyloxy)ethyl]-,(αS)-;Benzenemethanamine,N,N-dimethyl-α-[2-(1-naphthalenyloxy)ethyl]-,(S)-;(αS)-N,N-Dimethyl-α-[2-(1-naphthalenyloxy)ethyl]benzenemethanamine;Dapoxetine;LY 210448;(S)-(+)-Dapoxetine;(S)-(+)-N,N-Dimethyl-α-[2-(1-naphthalenyloxy)ethyl]benzenemethanamine;(S)-(+)-N,N-Dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine;(1S)-N,N-Dimethyl-3-naphthalen-1-yloxy-1-phenylpropan-1-amine
Categories:
Active Pharmaceutical Ingredients > Circulatory System Drugs

Description

Premature ejaculation (PE) is the most common male sexual dysfunction. Dapoxetine hydrochloride,marketed as Priligy and Westoxetin, is a class of PE treatment drugs known as selective serotonin reuptake inhibitors (SSRI) , was the first drug originally approved for the on-demand treatment of men 18–64 years old with PE. Dapoxetine works by inhibiting the serotonin transporter, increasing serotonin's action at the post synaptic cleft, and as a result promoting ejaculatory delay.

Dapoxetine is a member of naphthalenes.|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.

Dapoxetine Basic Attributes

Molecular Weight：

341.88

Exact Mass：

305.41

UNII：

GB2433A4M3

DSSTox ID：

DTXSID0057627

ATC Code：

G04BX14|G - Genito urinary system and sex hormones

HScode：

2922299090

Characteristics

PSA：

12.5

XLogP3：

5.13

Density：

1.081±0.06 g/cm3(Predicted)

Boiling Point：

454.4±38.0 °C(Predicted)

Flash Point：

132.6±29.1 °C

Refractive Index：

1.607

Safety Information

Precautionary statement(s)：

P264, P270, P273, P280, P301+P312, P305+P351+P338, P330, P337+P313, P501

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (97.67%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P280, P301+P312, P305+P351+P338, P330, P337+P313, and P501|Aggregated GHS information provided by 43 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

Drug Indication：

For the treatment of premature ejaculation.

Pharmacology：

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).

Absorption：

Rapidly absorbed.

Biological Half-Life：

Initial half-life of 1-2 hours.

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.

MeSH Entry Terms：

dapoxetine

Dapoxetine Use and Manufacturing

Antidepressant.White crystal powder with sweet taste and no odor, hygroscopic and soluble in water. It has a stable chemical property with the melting point at 175~177℃.Oral administration of one pill 20-30 mins before sexual intercourse； it can be taken irregularly; it’s better to take it with an empty stomach; avoid fatty food during administration; no tea before administration. Its effect is significant when the user under sexual stimulus.

Computed Properties

Molecular Weight:305.4
XLogP3:5.1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:6
Exact Mass:305.177964357
Monoisotopic Mass:305.177964357
Topological Polar Surface Area:12.5
Heavy Atom Count:23
Complexity:337
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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