Details of the Drug

General Information of Drug (ID: DMYN8MA)

Drug Name

Tianeptine

Synonyms

Tianeptina; Tianeptinum; Tianeptine Acid; Tianeptine [INN]; Stablon (TN); Tianeptine (INN); (1)-7-((3-Chloro-6,11-dihydro-6-methyldibenzo(c,f)(1,2)thiazepin-11-yl)amino)heptanoic acid S,S-dioxide; 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

Indication

Disease Entry	ICD 11	Status	REF
Major depressive disorder	6A70.3	Approved	[1]

Affected Organisms

Humans

ATC Code

N06AX14: Tianeptine

N06AX: Other antidepressants

N06A: ANTIDEPRESSANTS

N06: PSYCHOANALEPTICS

N: NERVOUS SYSTEM

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

437

Logarithm of the Partition Coefficient (xlogp)

1.2

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Bioavailability: The bioavailability of drug is 99% [2]
Clearance: The drug is rapidly cleared by the kidneys [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 2.5 hours [4]
Metabolism: The drug is metabolized via the beta-oxidation of its heptanoic side chain [5]
Unbound Fraction: The unbound fraction of drug in plasma is 0.05% [6]
Vd: The volume of distribution (Vd) of drug is 0.8 L/kg [4]

Chemical Identifiers

Formula: C21H25ClN2O4S
IUPAC Name: 7-[(3-chloro-6-methyl-5,5-dioxo-11H-benzo[c][2,1]benzothiazepin-11-yl)amino]heptanoic acid
Canonical SMILES: CN1C2=CC=CC=C2C(C3=C(S1(=O)=O)C=C(C=C3)Cl)NCCCCCCC(=O)O
InChI: 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

Cross-matching ID

PubChem CID: 68870
ChEBI ID: CHEMBL91749
CAS Number: 72797-41-2
UNII: 0T493YFU8O
DrugBank ID: DB09289
TTD ID: D06CVT
VARIDT ID: DR01101
INTEDE ID: DR1589

Drug Pharmacogenomic Perturbation (DPP)^NEW

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Drug ADMET Endpoint Profile (DAE)^NEW

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Serotonin transporter (SERT)	TT3ROYC	SC6A4_HUMAN	Inhibitor	[7]

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)_{Main DME}	DE4LYSA	CP3A4_HUMAN	Substrate	[8]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Mu-type opioid receptor (OPRM1)	OT16AAT8	OPRM_HUMAN	Gene/Protein Processing	[9]

Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Major depressive disorder

ICD Disease Classification

6A70.3

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Serotonin transporter (SERT)	DTT	SLC6A4	8.76E-01	7.18E-05	6.19E-04
Cytochrome P450 3A4 (CYP3A4)	DME	CYP3A4	1.76E-01	1.26E-01	8.27E-01

Molecular Expression Atlas (MEA)

MEA Detail

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References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7558).
2	Salvadori C, Ward C, Defrance R, Hopkins R: The pharmacokinetics of the antidepressant tianeptine and its main metabolite in healthy humans--influence of alcohol co-administration. Fundam Clin Pharmacol. 1990;4(1):115-25.
3	Antidepressants: Past, Present and Future
4	Pharmacokinetic and metabolic parameters of tianeptine in healthy volunteers and in populations with risk factors. Clin Neuropharmacol. 1988;11 Suppl 2:S90-6.
5	Briciu C, Neag M, Muntean D, Bocsan C, Buzoianu A, Antonescu O, Gheldiu AM, Achim M, Popa A, Vlase L: Phenotypic differences in nebivolol metabolism and bioavailability in healthy volunteers. Clujul Med. 2015;88(2):208-13. doi: 10.15386/cjmed-395. Epub 2015 Apr 15.
6	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
7	Emerging treatments for depression. Expert Opin Pharmacother. 2006 Dec;7(17):2323-39.
8	Tianeptine: a facilitator of the reuptake of serotonin and norepinephrine as an antidepressant? J Psychiatr Pract. 2004 Sep;10(5):323-30.
9	In vitro functional characterization of a panel of non-fentanyl opioid new psychoactive substances. Arch Toxicol. 2020 Nov;94(11):3819-3830. doi: 10.1007/s00204-020-02855-7. Epub 2020 Jul 31.