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

General Information of Drug (ID: DR1589)
Drug Name
Tianeptine
Synonyms
Tianeptina; Tianeptine; Tianeptine (INN); Tianeptine Acid; Tianeptine [INN]; XV6773012I; (+)-Tianeptine; (-)-Tianeptine; 66981-73-5; 7-((3-Chloro-6-methyl-5,5-dioxido-6,11-dihydrodibenzo[c,f][1,2]thiazepin-11-yl)amino)heptanoic acid; 7-[(3-chloro-6-methyl-5,5-dioxido-6,11-dihydrodibenzo[c,f][1,2]thiazepin-11-yl)amino]heptanoic acid; 7-[(3-chloro-6-methyl-5,5-dioxo-11H-benzo[c][2,1]benzothiazepin-11-yl)amino]heptanoic acid; 72797-41-2; AKU7QFL9ZT; Q-100759; Stablon (TN); EINECS 276-851-9; UNII-AKU7QFL9ZT; UNII-XV6773012I
Indication Depression [ICD11: 6A71] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 437 Topological Polar Surface Area 95.1
Heavy Atom Count 29 Rotatable Bond Count 8
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
68870
PubChem SID
6243297 ; 8192407 ; 14930306 ; 17396746 ; 43125383 ; 49834577 ; 57317121 ; 78806126 ; 85175447 ; 91616270 ; 92719757 ; 99381468 ; 104343282 ; 117461940 ; 118844741 ; 123087233 ; 125355861 ; 126620557 ; 126655743 ; 126669538 ; 128278297 ; 131323118 ; 134338709 ; 135204769 ; 135259984 ; 137172964 ; 142970937 ; 152040009 ; 152258933 ; 160647777 ; 162178730 ; 163068340 ; 164234531 ; 164765590 ; 164814565 ; 177748539 ; 179226145 ; 185990403 ; 187072591 ; 211536271 ; 223365894 ; 223387136 ; 223678309 ; 223704753 ; 224381628 ; 226433082 ; 242455962 ; 252357546 ; 252357547 ; 252424765
ChEBI ID
CHEBI:91749
CAS Number
26638-66-4
TTD Drug ID
D06CVT
Formula
C21H25ClN2O4S
Canonical SMILES
CN1C2=CC=CC=C2C(C3=C(S1(=O)=O)C=C(C=C3)Cl)NCCCCCCC(=O)O
InChI
1S/C21H25ClN2O4S/c1-24-18-9-6-5-8-16(18)21(23-13-7-3-2-4-10-20(25)26)17-12-11-15(22)14-19(17)29(24,27)28/h5-6,8-9,11-12,14,21,23H,2-4,7,10,13H2,1H3,(H,25,26)
InChIKey
JICJBGPOMZQUBB-UHFFFAOYSA-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
Tianeptine metabolite DM005785
5487151
Oxidation - #NAME? 1 [3] , [4]
Tianeptine metabolite M DM005782
57824321
Oxidation - Oxidationn 1 [3] , [4]
Unclear DM009999 N. A. Unclear 1 [2]
Tianeptine metabolite DM005786
57824331
Oxidation - #NAME? 2 [3] , [4]
Tianeptine metabolite LMC5 DM005787
101588787
Other reaction - Lactamization 2 [3] , [4]
Tianeptine metabolite N DM005783
14950938
Oxidation - N-dealkylation 2 [3] , [4]
Unclear DM009999 N. A. Oxidation - N-dealkylation 3 [3] , [4]
Tianeptine metabolite P DM005784 N. A. Reduction - Reduction 4 [3] , [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006175 Tianeptine Tianeptine metabolite M Oxidation - Oxidationn Unclear [3], [4]
MR006179 Tianeptine Tianeptine metabolite Oxidation - #NAME? Unclear [3], [4]
MR006182 Tianeptine Unclear Unclear CYP3A4 [2]
MR006180 Tianeptine metabolite Tianeptine metabolite Oxidation - #NAME? Unclear [3], [4]
MR006181 Tianeptine metabolite Tianeptine metabolite LMC5 Other reaction - Lactamization Unclear [3], [4]
MR006176 Tianeptine metabolite M Tianeptine metabolite N Oxidation - N-dealkylation Unclear [3], [4]
MR006177 Tianeptine metabolite N Unclear Oxidation - N-dealkylation Unclear [3], [4]
MR006178 Unclear Tianeptine metabolite P Reduction - Reduction Unclear [3], [4]
⏷ Show the Full List of 8 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 ClinicalTrials.gov (NCT01309776) Comparison of Tianeptine Versus Escitalopram Patients Major Depressive Disorder.
2 Tianeptine: a facilitator of the reuptake of serotonin and norepinephrine as an antidepressant? J Psychiatr Pract. 2004 Sep;10(5):323-30.
3 Ion-pair extraction and high-performance liquid chromatographic determination of tianeptine and its metabolites in human plasma, urine and tissues
4 The metabolic pathways of tianeptine, a new antidepressant, in healthy volunteers

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