ContaminantDB: Dapoxetine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 07:16:47 UTC

Update Date

2016-11-09 01:16:14 UTC

Accession Number

CHEM020626

Identification

Common Name

Dapoxetine

Class

Small Molecule

Description

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.

Contaminant Sources

STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Priligy	MeSH
N,N-Dimethyl-alpha-(2-(1-naphthalenyloxy)ethyl)benzenemethanamine	MeSH
Dapoxetine hydrochloride	MeSH

Chemical Formula

C₂₁H₂₃NO

Average Molecular Mass

305.413 g/mol

Monoisotopic Mass

305.178 g/mol

CAS Registry Number

119356-77-3

IUPAC Name

dimethyl[(1S)-3-(naphthalen-1-yloxy)-1-phenylpropyl]amine

Traditional Name

dapoxetine

SMILES

CN(C)[C@@H](CCOC1=CC=CC2=CC=CC=C12)C1=CC=CC=C1

InChI Identifier

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

InChI Key

USRHYDPUVLEVMC-FQEVSTJZSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as naphthalenes. Naphthalenes 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

Substituents

Naphthalene
Aralkylamine
Alkyl aryl ether
Monocyclic benzene moiety
Tertiary aliphatic amine
Tertiary amine
Ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00084 g/L	ALOGPS
logP	4.75	ALOGPS
logP	4.67	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Basic)	9.04	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

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0319000000-de474915fcd40bfbbdc4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-08fr-0922000000-eb3b9d9243b6bfea0cc1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02c2-3900000000-0d0df9126ae3beeed9e3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0409000000-88756d023eb4543ddbb2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0903000000-954fd1c46260559c97ee	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-0900000000-d4e6c17e4d4777a2310f	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB04884

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Dapoxetine

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

71353

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Dapoxetine (CHEM020626)

Structure for CHEM020626: Dapoxetine