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

General Information of Drug (ID: DR1477)
Drug Name
Sertraline hydrochloride
Synonyms
Sertraline (hydrochloride); Sertraline HCl; Sertraline hydrochloride; Sertralina; Sertralina [Spanish]; Sertraline [INN:BAN]; Sertraline [Zoloft]; Sertralinum; Sertralinum [Latin]; UNII-QUC7NX6WMB; VGKDLMBJGBXTGI-SJCJKPOMSA-N; cis-(+)-sertraline; sertraline; sertraline (Zoloft); (+)-Sertraline; (1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine; (1S,4S)-sertraline; (1S-cis)-1,2,3,4-Tetrahydro-4-(3,4-dichlorophenyl)-N-methyl-1-naphthalenamine; 79617-96-2; Apo-Sertraline; BRN 5753709; CHEBI:9123; CHEMBL809; Cp 51974; HSDB 7037; QUC7NX6WMB; Tatig; Tresleen; UNII-UTI8907Y6X; UTI8907Y6X; (+)-sertraline hydrochloride; (1S,4S)-1-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-4-(methylamino)naphthalene Hydrochloride; (1S,4S)-4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine hydrochloride; (1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine hydrochloride; 79559-97-0; Atruline; CHEBI:9124; CPD000466298; Cp 51,974-1; Gladem; MFCD00895772; Serad
Indication Depression [ICD11: 6A71] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 342.7 Topological Polar Surface Area 12
Heavy Atom Count 21 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 1
Cross-matching ID
PubChem CID
63009
ChEBI ID
CHEBI:9124
CAS Number
79559-97-0
TTD Drug ID
D0K0TC
Formula
C17H18Cl3N
Canonical SMILES
CNC1CCC(C2=CC=CC=C12)C3=CC(=C(C=C3)Cl)Cl.Cl
InChI
1S/C17H17Cl2N.ClH/c1-20-17-9-7-12(13-4-2-3-5-14(13)17)11-6-8-15(18)16(19)10-11;/h2-6,8,10,12,17,20H,7,9H2,1H3;1H/t12-,17-;/m0./s1
InChIKey
BLFQGGGGFNSJKA-XHXSRVRCSA-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
Desmethylsertraline DM001305
114743
Oxidation - N-Demethylation 1 [4] , [9] , [10] , [11]
Alpha-hydroxy sertraline ketone DM001306 N. A. Oxidation - N-Hydroxylation 2 [8]
Alpha-hydroxy sertraline ketone glucuronide DM001308 N. A. Oxidation - N-Hydroxylation; Glucuronidation 2 [12]
Sertraline carbamoyl-O-glucuronide DM001307
71752187
Conjugation - O-Glucuronidation 3 [8]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002247 Sertraline hydrochloride Desmethylsertraline Oxidation - N-Demethylation CYP3A4 ... [4], [9], [10], [11]
MR002244 Desmethylsertraline Alpha-hydroxy sertraline ketone Oxidation - N-Hydroxylation MAOA ... [8]
MR002245 Desmethylsertraline Alpha-hydroxy sertraline ketone glucuronide Oxidation - N-Hydroxylation; Glucuronidation Unclear [12]
MR002246 Alpha-hydroxy sertraline ketone Sertraline carbamoyl-O-glucuronide Conjugation - O-Glucuronidation UGT [8]
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 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[4]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[5]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[6]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[7]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[3]
Monoamine oxidase type A (MAO-A) DME0044 Homo sapiens
AOFA_HUMAN
1.4.3.4
[8]
Monoamine oxidase type B (MAO-B) DME0045 Homo sapiens
AOFB_HUMAN
1.4.3.4
[8]
⏷ Show the Full List of 9  DME(s)
References
1 Sertraline Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 The selective serotonin reuptake inhibitor sertraline: its profile and use in psychiatric disorders. CNS Drug Rev. 2001 Spring;7(1):1-24.
3 Influence of CYP2B6 and CYP2C19 polymorphisms on sertraline metabolism in major depression patients. Int J Clin Pharm. 2016 Apr;38(2):388-94.
4 Sertraline is metabolized by multiple cytochrome P450 enzymes, monoamine oxidases, and glucuronyl transferases in human: an in vitro study. Drug Metab Dispos. 2005 Feb;33(2):262-70.
5 Some aspects of genetic polymorphism in the biotransformation of antidepressants. Therapie. 2004 Jan-Feb;59(1):5-12.
6 PharmGKB: A worldwide resource for pharmacogenomic information. Wiley Interdiscip Rev Syst Biol Med. 2018 Jul;10(4):e1417. (ID: PA166181117)
7 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.
8 DrugBank(Pharmacology-Metabolism)Sertraline hydrochloride
9 Pharmacogenetic Testing and Therapeutic Drug Monitoring Of Sertraline at a Residential Treatment Center for Children and Adolescents: A Pilot Study. Innov Pharm. 2022 Dec 26;13(4):10.24926/iip.v13i4.5035. doi: 10.24926/iip.v13i4.5035.
10 Sertraline. 2022 May 15. Drugs and Lactation Database (LactMed?) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006C.
11 Neonicotinoids and pharmaceuticals in hair of the Red fox (Vulpes vulpes) from the Cavallino-Treporti peninsula, Italy. Environ Res. 2023 Jul 1;228:115837. doi: 10.1016/j.envres.2023.115837.
12 Absorption, metabolism and excretion of the GLP-1 analogue semaglutide in humans and nonclinical species. Eur J Pharm Sci. 2017 Jun 15;104:31-41.

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