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

General Information of Drug (ID: DR0554)
Drug Name
Duloxetine hydrochloride
Synonyms
Duloxetine (hydrochloride); Duloxetine HCl; Duloxetine hydrochloride [USAN]; Duloxetine; (3S)-N-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propan-1-amine; (S)-Duloxetine; (S)-N-Methyl-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propan-1-amine; (S)-N-Methyl-gamma-(1-naphthalenyloxy)-2-thiophenepropanamine; 116539-59-4; CHEBI:36795; CPD000449282; Duloxetine [INN:BAN]; HSDB 7368; LY 248686; LY248686; MFCD06801358; N-Methyl-gama-(1-naphthalenyloxy)-2-thiophenepropanamine; O5TNM5N07U; UNII-O5TNM5N07U; Yentreve; LY-248686; Q-102508; UNII-9044SC542W; (3S)-N-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propan-1-amine hydrochloride; (S)-Duloxetine HCl; (S)-N-Methyl-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propan-1-amine hydrochloride; (S)-duloxetine hydrochloride; 136434-34-9; 9044SC542W; C18H19NOS.HCl; C18H20ClNOS; CHEBI:31526; CPD000469136; DSSTox_CID_26443; DSSTox_GSID_46443; DSSTox_RID_81618
Indication Depression [ICD11: 6A71] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 333.9 Topological Polar Surface Area 49.5
Heavy Atom Count 22 Rotatable Bond Count 6
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
60834
ChEBI ID
CHEBI:31526
CAS Number
136434-34-9
TTD Drug ID
D01AXB
Formula
C18H20ClNOS
Canonical SMILES
CNCCC(C1=CC=CS1)OC2=CC=CC3=CC=CC=C32.Cl
InChI
1S/C18H19NOS.ClH/c1-19-12-11-17(18-10-5-13-21-18)20-16-9-4-7-14-6-2-3-8-15(14)16;/h2-10,13,17,19H,11-12H2,1H3;1H/t17-;/m0./s1
InChIKey
BFFSMCNJSOPUAY-LMOVPXPDSA-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
4-hydroxy duloxetine DM006266
29981497
Oxidation - Hydrolyzationn 1 [2]
5-hydroxy duloxetine DM006260
44344235
Oxidation - Hydrolyzationn 1 [2]
6-hydroxy duloxetine DM006265
10086952
Oxidation - Hydrolyzationn 1 [2]
Dihydrodiol duloxetine DM006270 N. A. Unclear 1 [4]
N-desmethyl duloxetine DM006269
10107888
Unclear 1 [4]
Thinel alcohol+Naphthol DM006268
10095047
Unclear 1 [4]
4-hydroxy duloxetine glucuronide DM006267
29981513
Conjugation - Glucuronidation 2 [5]
Catechol duloxetine DM006261
44344115
Oxidation - Hydrolyzationn 2 [5]
5-hydroxy, 6-methoxy duloxetine DM006262
29981679
Conjugation - O-methylation 3 [5]
5-hydroxy, 6-methoxy duloxetine glucuronide DM006263 N. A. Conjugation - Glucuronidation 4 [5]
5-hydroxy, 6-methoxy duloxetine sulfate DM006264
131770039
Conjugation - Sulfation 4 [5]
⏷ Show the Full List of 11  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006715 Duloxetine hydrochloride 5-hydroxy duloxetine Oxidation - Hydrolyzationn CYP2C9 ... [2]
MR006720 Duloxetine hydrochloride 6-hydroxy duloxetine Oxidation - Hydrolyzationn Unclear [2]
MR006722 Duloxetine hydrochloride 4-hydroxy duloxetine Oxidation - Hydrolyzationn Unclear [2]
MR006724 Duloxetine hydrochloride Thinel alcohol+Naphthol Unclear Unclear [4]
MR006725 Duloxetine hydrochloride N-desmethyl duloxetine Unclear Unclear [4]
MR006726 Duloxetine hydrochloride Dihydrodiol duloxetine Unclear Unclear [4]
MR006723 4-hydroxy duloxetine 4-hydroxy duloxetine glucuronide Conjugation - Glucuronidation Unclear [5]
MR006716 5-hydroxy duloxetine Catechol duloxetine Oxidation - Hydrolyzationn Unclear [5]
MR006721 6-hydroxy duloxetine Catechol duloxetine Oxidation - Hydrolyzationn Unclear [5]
MR006717 Catechol duloxetine 5-hydroxy, 6-methoxy duloxetine Conjugation - O-methylation Unclear [5]
MR006718 5-hydroxy, 6-methoxy duloxetine 5-hydroxy, 6-methoxy duloxetine glucuronide Conjugation - Glucuronidation Unclear [5]
MR006719 5-hydroxy, 6-methoxy duloxetine 5-hydroxy, 6-methoxy duloxetine sulfate Conjugation - Sulfation Unclear [5]
⏷ Show the Full List of 12 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1265 Escherichia coli Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1364 Bacteroides coprophilus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1376 Bacteroides ovatus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1416 Enterobacter cancerogenus Not Available Not Available [3]
⏷ Show the Full List of 11  DME(s)
References
1 Duloxetine Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Duloxetine: clinical pharmacokinetics and drug interactions. Clin Pharmacokinet. 2011 May;50(5):281-94.
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
4 Metabolism, excretion, and pharmacokinetics of duloxetine in healthy human subjects
5 DrugBank(Pharmacology-Metabolism):Duloxetine

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