Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0414)
Drug Name
Dapoxetine
Synonyms
Dapoxetina; Dapoxetina [INN-Spanish]; Dapoxetine; Dapoxetine [INN]; Dapoxetine hydrochloride; Dapoxetinum; Dapoxetinum [INN-Latin]; GB2433A4M3; Kutub, Priligy, Duratia; LY 210448; LY-210448; LY210448; (+)-Dapoxetine; (1S)-N,N-dimethyl-3-naphthalen-1-yloxy-1-phenylpropan-1-amine; (1s)-n,n-dimethyl-3-(1-naphthyloxy)-1-phenylpropan-1-amine; (S)-N,N-Dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine; 119356-77-3; Benzenemethanamine, N,N-dimethyl-alpha-(2-(1-naphthalenyloxy)ethyl)-, (+)-; DSSTox_RID_97302; UNII-GB2433A4M3
Indication Ejaculatory dysfunction [ICD11: HA03] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 305.4 Topological Polar Surface Area 12.5
Heavy Atom Count 23 Rotatable Bond Count 6
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
71353
PubChem SID
8194577 ; 14849767 ; 14923158 ; 43127692 ; 49880434 ; 57318151 ; 79154397 ; 103065098 ; 103078304 ; 104350255 ; 117555106 ; 121277907 ; 126629125 ; 135029363 ; 135929225 ; 137249315 ; 140744274 ; 152034602 ; 152164187 ; 160839263 ; 162180638 ; 162224681 ; 163099314 ; 163402775 ; 163884608 ; 164788309 ; 170466555 ; 172091693 ; 172913400 ; 174006832 ; 175426887 ; 176484780 ; 179149672 ; 198971449 ; 204429427 ; 223535479 ; 223656149 ; 224680431 ; 226420934 ; 242549858 ; 242590301 ; 249565584 ; 249865605 ; 251916780 ; 251918019 ; 252077306 ; 252347836 ; 252430157
ChEBI ID
CHEBI:135962
CAS Number
119356-77-3
TTD Drug ID
D0H5LK
Formula
C21H23NO
Canonical SMILES
CN(C)C(CCOC1=CC=CC2=CC=CC=C21)C3=CC=CC=C3
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
InChIKey
USRHYDPUVLEVMC-FQEVSTJZSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Dapoxetine Metabolite M1 DM006559
11779061
Oxidation - N-dealkylation 1 [4]
Dapoxetine Metabolite M11 DM006564
87581357
Other reaction - Deacylation 1 [4]
Dapoxetine Metabolite M3 DM006563 N. A. Oxidation - Hydrolyzationn 1 [4]
Dapoxetine Metabolite M7 DM006568 N. A. Oxidation - Hydrolyzationn 1 [4]
Dapoxetine-n-oxide DM006566
71315184
Oxidation - Oxidationn 1 [4]
Didesmethyldapoxetine DM006570
60166945
Unclear 1 [2]
Dapoxetine Metabolite M10 DM006567 N. A. Oxidation - Hydrolyzationn 2 [4]
Dapoxetine Metabolite M2 DM006560 N. A. Oxidation - Demethylation 2 [4]
Dapoxetine Metabolite M2 DM006560 N. A. Oxidation - Hydrolyzationn 2 [4]
Dapoxetine Metabolite M4 DM006565
12520910
Other reaction - Deacylation 2 [4]
Dapoxetine Metabolite M8 DM006569 N. A. Oxidation - Demethylation 2 [4]
Desmethyldapoxetine DM006562
19884996
Oxidation - Demethylation 2 [2] , [5] , [6]
Dapoxetine Metabolite M9 DM006561 N. A. Oxidation - Demethylation 3 [4]
⏷ Show the Full List of 13  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007073 Dapoxetine Dapoxetine Metabolite M1 Oxidation - N-dealkylation Unclear [4]
MR007077 Dapoxetine Dapoxetine Metabolite M3 Oxidation - Hydrolyzationn Unclear [4]
MR007079 Dapoxetine Dapoxetine Metabolite M11 Other reaction - Deacylation Unclear [4]
MR007081 Dapoxetine Dapoxetine-n-oxide Oxidation - Oxidationn CYP2D6 [4]
MR007083 Dapoxetine Dapoxetine Metabolite M7 Oxidation - Hydrolyzationn Unclear [4]
MR007085 Dapoxetine Didesmethyldapoxetine Unclear Unclear [2]
MR007074 Dapoxetine Metabolite M1 Dapoxetine Metabolite M2 Oxidation - Hydrolyzationn Unclear [4]
MR007076 Dapoxetine Metabolite M1 Desmethyldapoxetine Oxidation - Demethylation CYP3A4 ... [2], [5], [6]
MR007080 Dapoxetine Metabolite M11 Dapoxetine Metabolite M4 Other reaction - Deacylation Unclear [4]
MR007078 Dapoxetine Metabolite M3 Dapoxetine Metabolite M2 Oxidation - Demethylation Unclear [4]
MR007084 Dapoxetine Metabolite M7 Dapoxetine Metabolite M8 Oxidation - Demethylation Unclear [4]
MR007082 Dapoxetine-n-oxide Dapoxetine Metabolite M10 Oxidation - Hydrolyzationn Unclear [4]
MR007075 Dapoxetine Metabolite M2 Dapoxetine Metabolite M9 Oxidation - Demethylation Unclear [4]
⏷ Show the Full List of 13 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Dimethylaniline oxidase 1 (FMO1) DME0059 Homo sapiens
FMO1_HUMAN
1.14.13.8
[3]
References
1 ClinicalTrials.gov (NCT01273545) PRILIGY Usage Patterns in Selected Populations.
2 Dapoxetine: a new option in the medical management of premature ejaculation. Ther Adv Urol. 2012 Oct;4(5):233-51.
3 Pharmacokinetics of single and multiple escalating doses of dapoxetine in healthy volunteers. Clinical Pharmacology Therapeutics, 2004, 75(2):P32.
4 Characterization of Phase I Hepatic Metabolites of Anti-Premature Ejaculation Drug Dapoxetine by UHPLC-ESI-Q-TOF
5 Effects of Evodiamine on the Pharmacokinetics of Dapoxetine and Its Metabolite Desmethyl Dapoxetine in Rats
6 Effects of 22 novel CYP2D6 variants found in Chinese population on the metabolism of dapoxetine

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