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

General Information of Drug (ID: DR1245)
Drug Name
Paroxetine hydrochloride
Synonyms
Paroxetine Hcl; Paroxetine hydrochloride; Paroxetine hydrochloride [USP]; Paxil (TN); SDB 7175; paroxetine (hydrochloride); (3S,4R)-3-((Benzo[d][1,3]dioxol-5-yloxy)methyl)-4-(4-fluorophenyl)piperidine hydrochloride; 110429-35-1; 3I3T11UD2S; 78246-49-8; BRL 29060 hydrochloride; BRL 29060A; BRL29060A; C19H21ClFNO3; HSDB 7175; Paroxetine hydrochloride hemihydrate; Paroxetine hydrochloride hemihydrate (MW = 374.83); Paxil; S3005; UNII-3I3T11UD2S; Aropax; Aropax 20; Paroxat; [3H]-Paroxetine; [3H]Paroxetine; AHOUBRCZNHFOSL-RXMHWKDRSA-N; CHEMBL1628650; GTPL4561
Indication Depression [ICD11: 6A71] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 365.8 Topological Polar Surface Area 39.7
Heavy Atom Count 25 Rotatable Bond Count 4
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
62878
ChEBI ID
CHEBI:7944
CAS Number
78246-49-8
TTD Drug ID
D06GDY
Formula
C19H21ClFNO3
Canonical SMILES
C1CNCC(C1C2=CC=C(C=C2)F)COC3=CC4=C(C=C3)OCO4.Cl
InChI
1S/C19H20FNO3.ClH/c20-15-3-1-13(2-4-15)17-7-8-21-10-14(17)11-22-16-5-6-18-19(9-16)24-12-23-18;/h1-6,9,14,17,21H,7-8,10-12H2;1H/t14-,17-;/m0./s1
InChIKey
GELRVIPPMNMYGS-RVXRQPKJSA-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
Paroxetine catechol DM001177
162260575
Unclear 1 [8] , [6]
(-)-trans-4-[4-(4'-Fluorophenyl)-3-piperidinylmethoxy]-2-methoxyphenol DM001178
10359344
Conjugation - Methylation 2 [6]
(3S-trans)-5-[[4-(4-Fluorophenyl)-3-piperidinyl]methoxy]-2-methoxyphenol DM001181
87196
Conjugation - Methylation 2 [6]
4-(4-Fluorophenyl)-3-(4-hydroxy-3-methoxyphenoxymethyl)piperidine DM001179
163876
Conjugation - Methylation 2 [6]
4-(4-Fluorophenyl)-3-(4-methoxy-3-hydroxyphenoxymethyl)piperidine DM001180
53416071
Conjugation - Methylation 2 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003337 Paroxetine hydrochloride Paroxetine catechol Unclear CYP2D6 ... [8], [6]
MR003333 Paroxetine catechol (-)-trans-4-[4-(4'-Fluorophenyl)-3-piperidinylmethoxy]-2-methoxyphenol Conjugation - Methylation Unclear [6]
MR003334 Paroxetine catechol 4-(4-Fluorophenyl)-3-(4-hydroxy-3-methoxyphenoxymethyl)piperidine Conjugation - Methylation Unclear [6]
MR003335 Paroxetine catechol 4-(4-Fluorophenyl)-3-(4-methoxy-3-hydroxyphenoxymethyl)piperidine Conjugation - Methylation Unclear [6]
MR003336 Paroxetine catechol (3S-trans)-5-[[4-(4-Fluorophenyl)-3-piperidinyl]methoxy]-2-methoxyphenol Conjugation - Methylation Unclear [6]
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 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[5]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[6]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [7]
⏷ Show the Full List of 6  DME(s)
References
1 Paroxetine Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 CYP1A2 genetic polymorphisms are associated with treatment response to the antidepressant paroxetine. Pharmacogenomics. 2010 Nov;11(11):1535-43.
3 Clinical pharmacogenetics implementation consortium (CPIC) guideline for CYP2D6 and CYP2C19 genotypes and dosing of selective serotonin reuptake inhibitors. Clin Pharmacol Ther. 2015 Aug;98(2):127-34.
4 New orally active anticoagulant agents for the prevention and treatment of venous thromboembolism in cancer patients. Ther Clin Risk Manag. 2014 Jun 13;10:423-36.
5 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development Curr Med Chem. 2009;16(27):3480-675. doi: 10.2174/092986709789057635.
6 Identification of cytochrome P450 isoforms involved in the metabolism of paroxetine and estimation of their importance for human paroxetine metabolism using a population-based simulator. Drug Metab Dispos. 2010 Mar;38(3):376-85.
7 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
8 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.

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