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]
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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: CHEBI:91749
CAS Number: 72797-41-2
UNII: 0T493YFU8O
DrugBank ID: DB09289
TTD ID: D06CVT
VARIDT ID: DR01101
INTEDE ID: DR1589

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]

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Drug-Metabolizing Enzyme (DME)

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

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Angiopoietin-related protein 3 (ANGPTL3)	OTCD5Z9W	ANGL3_HUMAN	Gene/Protein Processing	[9]
Insulin-like growth factor-binding protein 1 (IGFBP1)	OT6UQV2K	IBP1_HUMAN	Gene/Protein Processing	[9]
Mu-type opioid receptor (OPRM1)	OT16AAT8	OPRM_HUMAN	Gene/Protein Processing	[10]
Sterol regulatory element-binding protein 1 (SREBF1)	OTWBRPAI	SRBP1_HUMAN	Gene/Protein Processing	[9]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

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

Jump to Detail Molecular Expression Atlas of This Drug

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	Advantageous use of HepaRG cells for the screening and mechanistic study of drug-induced steatosis. Toxicol Appl Pharmacol. 2016 Jul 1;302:1-9. doi: 10.1016/j.taap.2016.04.007. Epub 2016 Apr 16.
10	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.