Identification

Name
Tianeptine
Accession Number
DB09289
Type
Small Molecule
Groups
Approved, Investigational
Description

Tianeptine is a drug used primarily in the treatment of major depressive disorder and has been studied in the treatment of irritable bowel syndrome (IBS) [3]. Structurally, it is classified as a tricyclic antidepressant (TCA), but it possesses different pharmacological properties than typical tricyclic antidepressants [1].

Tianeptine was discovered and patented by The French Society of Medical Research in the 1960s. Currently, tianeptine is approved in France and manufactured and marketed by Laboratories Servier SA; it is also marketed in several other European countries under the trade name “Coaxil” as well as in Asia (including Singapore) and Latin America as “Stablon” and “Tatinol” but it is not available in Australia, Canada, New Zealand, the U.K. or the U.S.

Structure
Thumb
Synonyms
Not Available
Product Ingredients
IngredientUNIICASInChI Key
Tianeptine sodiumYG0E19592I30123-17-2ZLBSUOGMZDXYKE-UHFFFAOYSA-M
International/Other Brands
Coaxil / Neptine (Hanmi South Korea) / Salymbra / Stablon / Tatinol / Tianeurax / Zinosal
Categories
UNII
0T493YFU8O
CAS number
72797-41-2
Weight
Average: 436.952
Monoisotopic: 436.122355695
Chemical Formula
C21H25ClN2O4S
InChI Key
JICJBGPOMZQUBB-UHFFFAOYSA-N
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)
IUPAC Name
7-({6-chloro-10-methyl-9,9-dioxo-9λ⁶-thia-10-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaen-2-yl}amino)heptanoic acid
SMILES
CN1C2=CC=CC=C2C(NCCCCCCC(O)=O)C2=C(C=C(Cl)C=C2)S1(=O)=O

Pharmacology

Indication

Used primarily in the treatment of major depressive disorder and anxiety [1]. It is currently being studied for fibromyalgia pain treatment [16].

Structured Indications
Not Available
Pharmacodynamics

aneptine is a distinctive antidepressant and anxiolytic medication that stimulates the uptake of serotonin (5-hydroxytryptamine; 5-HT), and 5-hydroxyindoleacetic acid (5-HIAA) in brain tissue [2]. Although the monoaminergic neurotransmitters serotonin (5-HT), noradrenaline (NA) and dopamine (DA) are proven to be related to the occurrence of depressive disorders, it is now recognized that monoamine deficits are not sufficient to explain the mechanism of action of antidepressant medications [2]. Current research suggests that tianeptine produces its antidepressant effects through the modulation of glutamate receptor activity (for example, AMPA receptors and NMDA receptors) and affect the release of brain-derived neurotrophic factor (BDNF), which impacts neural plasticity [4]. Tianeptine reduces the hypothalamic-pituitary-adrenal response to stress, and thus prevents stress-related behavioral issues [4, 5]. Tianeptine is effective in reducing depressive symptoms in mild to severe major depressive disorder and also alleviates anxious symptoms associated with depression without the need for coadministration of an anti-anxiety medication [2]. These findings, however, are met with controversial data. In a study of healthy volunteers, Tianeptine-treated subjects were less accurate at identifying facial expressions, suggesting a lack of improvement in the psychomotor symptoms of depression. The tianeptine group also showed reduced memory and reduced attentional vigilance to various stimuli [6].

Mechanism of action

Tianeptine has challenged the monoaminergic hypothesis of depression, as well as the widely supported monoaminergic mechanisms whereby the action of most known antidepressants have been explained [14]. Specifically, this drug is thought to persistently alter glutamate receptor bursting of the hippocampal CA3 commissural associational synapse [2]. More recent studies by support the role of tianeptine in the modulation of glutamatergic activity in the amygdala, the emotional region of the brain associated with memories [2]. In rodents, the stress of acute restraint increases extracellular levels of glutamate in the basolateral amygdala an effect that was inhibited by tianeptine [2]. Interestingly, the SSRI fluoxetine increased extracellular glutamate levels in the basolateral amygdala regardless of stress conditions. These data demonstrate that the mechanism of action of tianeptine is distinct from SSRIs and support the hypothesis that the mechanism of action of tianeptine relates to alteration of glutaminergic activity in the amygdala and the hippocampus [2, 4].

Analyses in large-scale epidemiologic surveys have shown that the anxiety disorders are widely comorbid with major depression. This makes antidepressant with anxiolytic properties particularly unique and attractive [2].

TargetActionsOrganism
USodium-dependent serotonin transporterNot AvailableHuman
U5-hydroxytryptamine receptor 1A
antagonist
Human
UGlutamate receptor 1Not AvailableHuman
Absorption

Well absorbed, approximately 99% bioavailability [9].

Volume of distribution

About 31% for adult females [18]. The average tianeptine volume of distribution at steady state dose in rats was 2.03 L/kg and the systemic clearance equaled 1.84 L/h/kg [10].

Protein binding

95% bound to plasma protein [18].

Metabolism

Tianeptine is metabolized primarily by beta-oxidation of its heptanoic side chain [7]. The metabolism of tianeptine was studied after a one-time oral administration of radioisotopically (14C) labeled compound to healthy male volunteers. After 1 week, approximately 66% of the dose was eliminated by the kidneys (55% elimination during the first 24 hr). After 24h, unchanged drug 3% of the drug was found unchanged in the urine. Three major metabolites result from beta-oxidation of Tianeptine. The metabolite profiles of tianeptine in feces and plasma were found to be qualitatively similar to that in urine [8].

Route of elimination

Eliminated with bile as glucuronide and glutamine conjugates [10].

Half life

2.5h [L14529]

Clearance

Rapidly cleared by the kidneys [18].

Toxicity

There are several published case reports of tianeptine intoxication and death [21]. An overdose of tianeptine can lead to opiod-like effects and lead to respiratory failure and death, due to its direct effect on the mu opioid receptor [L14535]. In addition, cardiotoxicity can result from an overdose of this medication [21].

Affected organisms
  • Humans
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
1,10-PhenanthrolineThe serum concentration of Tianeptine can be increased when it is combined with 1,10-Phenanthroline.Experimental
2,5-Dimethoxy-4-ethylamphetamineTianeptine may increase the stimulatory activities of 2,5-Dimethoxy-4-ethylamphetamine.Experimental, Illicit
2,5-Dimethoxy-4-ethylthioamphetamineTianeptine may increase the stimulatory activities of 2,5-Dimethoxy-4-ethylthioamphetamine.Experimental
3,4-DichloroisocoumarinThe serum concentration of Tianeptine can be increased when it is combined with 3,4-Dichloroisocoumarin.Experimental
3,4-MethylenedioxyamphetamineTianeptine may increase the stimulatory activities of 3,4-Methylenedioxyamphetamine.Experimental, Illicit
4-(2-Aminoethyl)Benzenesulfonyl FluorideThe serum concentration of Tianeptine can be increased when it is combined with 4-(2-Aminoethyl)Benzenesulfonyl Fluoride.Experimental
4-Bromo-2,5-dimethoxyamphetamineTianeptine may increase the stimulatory activities of 4-Bromo-2,5-dimethoxyamphetamine.Experimental, Illicit
4-MethoxyamphetamineTianeptine may decrease the antihypertensive activities of 4-Methoxyamphetamine.Experimental, Illicit
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when Tianeptine is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.Experimental
AcenocoumarolTianeptine may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
AgmatineTianeptine may decrease the antihypertensive activities of Agmatine.Experimental, Investigational
AlogliptinThe serum concentration of Tianeptine can be increased when it is combined with Alogliptin.Approved
Alpha-1-proteinase inhibitorThe serum concentration of Tianeptine can be increased when it is combined with Alpha-1-proteinase inhibitor.Approved
AltretamineAltretamine may increase the orthostatic hypotensive activities of Tianeptine.Approved
AmobarbitalThe metabolism of Tianeptine can be increased when combined with Amobarbital.Approved, Illicit
AmphetamineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Amphetamine.Approved, Illicit, Investigational
AmprenavirThe serum concentration of Tianeptine can be increased when it is combined with Amprenavir.Approved, Investigational
Antithrombin III humanThe serum concentration of Tianeptine can be increased when it is combined with Antithrombin III human.Approved
ApixabanThe serum concentration of Tianeptine can be increased when it is combined with Apixaban.Approved
ApomorphineTianeptine may decrease the antihypertensive activities of Apomorphine.Approved, Investigational
ApraclonidineTianeptine may decrease the antihypertensive activities of Apraclonidine.Approved
AprotininThe serum concentration of Tianeptine can be increased when it is combined with Aprotinin.Approved, Investigational, Withdrawn
ArbutamineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Arbutamine.Approved
ArformoterolThe risk or severity of adverse effects can be increased when Tianeptine is combined with Arformoterol.Approved, Investigational
ArgatrobanThe serum concentration of Tianeptine can be increased when it is combined with Argatroban.Approved, Investigational
AsunaprevirThe serum concentration of Tianeptine can be increased when it is combined with Asunaprevir.Approved, Investigational, Withdrawn
AtazanavirThe serum concentration of Tianeptine can be increased when it is combined with Atazanavir.Approved, Investigational
BambuterolThe risk or severity of adverse effects can be increased when Tianeptine is combined with Bambuterol.Approved, Investigational
BarbexacloneThe metabolism of Tianeptine can be increased when combined with Barbexaclone.Experimental
BarbitalThe metabolism of Tianeptine can be increased when combined with Barbital.Illicit
BatimastatThe serum concentration of Tianeptine can be increased when it is combined with Batimastat.Experimental
BenazeprilThe serum concentration of Tianeptine can be increased when it is combined with Benazepril.Approved, Investigational
BenmoxinThe risk or severity of adverse effects can be increased when Tianeptine is combined with Benmoxin.Withdrawn
BenzamidineThe serum concentration of Tianeptine can be increased when it is combined with Benzamidine.Experimental
BenzphetamineTianeptine may decrease the antihypertensive activities of Benzphetamine.Approved, Illicit
BethanidineTianeptine may decrease the antihypertensive activities of Bethanidine.Approved
BivalirudinThe serum concentration of Tianeptine can be increased when it is combined with Bivalirudin.Approved, Investigational
BoceprevirThe serum concentration of Tianeptine can be increased when it is combined with Boceprevir.Approved, Withdrawn
BrimonidineTianeptine may decrease the antihypertensive activities of Brimonidine.Approved
BrofaromineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Brofaromine.Experimental
BromocriptineTianeptine may decrease the antihypertensive activities of Bromocriptine.Approved, Investigational
BupropionThe metabolism of Tianeptine can be decreased when combined with Bupropion.Approved
CamostatThe serum concentration of Tianeptine can be increased when it is combined with Camostat.Experimental
CandoxatrilThe serum concentration of Tianeptine can be increased when it is combined with Candoxatril.Experimental
CandoxatrilatThe serum concentration of Tianeptine can be increased when it is combined with Candoxatrilat.Experimental
CaptoprilThe serum concentration of Tianeptine can be increased when it is combined with Captopril.Approved
CarbamazepineThe metabolism of Tianeptine can be increased when combined with Carbamazepine.Approved, Investigational
CaroxazoneThe risk or severity of adverse effects can be increased when Tianeptine is combined with Caroxazone.Withdrawn
CeliprololThe risk or severity of adverse effects can be increased when Tianeptine is combined with Celiprolol.Approved, Investigational
ChlorphentermineTianeptine may increase the stimulatory activities of Chlorphentermine.Illicit, Withdrawn
CholesterolThe serum concentration of Tianeptine can be increased when it is combined with Cholesterol.Approved, Experimental, Investigational
ChymostatinThe serum concentration of Tianeptine can be increased when it is combined with Chymostatin.Experimental
CilastatinThe serum concentration of Tianeptine can be increased when it is combined with Cilastatin.Approved, Investigational
CilazaprilThe serum concentration of Tianeptine can be increased when it is combined with Cilazapril.Approved
CimetidineThe metabolism of Tianeptine can be decreased when combined with Cimetidine.Approved, Investigational
CinacalcetThe serum concentration of Tianeptine can be increased when it is combined with Cinacalcet.Approved
CirazolineTianeptine may increase the vasopressor activities of Cirazoline.Experimental
CitalopramThe risk or severity of adverse effects can be increased when Tianeptine is combined with Citalopram.Approved
ClenbuterolThe risk or severity of adverse effects can be increased when Tianeptine is combined with Clenbuterol.Approved, Investigational, Vet Approved
ClonidineTianeptine may decrease the antihypertensive activities of Clonidine.Approved
ClorindioneTianeptine may increase the anticoagulant activities of Clorindione.Experimental
Dabigatran etexilateThe serum concentration of Tianeptine can be increased when it is combined with Dabigatran etexilate.Approved
DarexabanThe serum concentration of Tianeptine can be increased when it is combined with Darexaban.Investigational
DarunavirThe serum concentration of Tianeptine can be increased when it is combined with Darunavir.Approved
DelanzomibThe serum concentration of Tianeptine can be increased when it is combined with Delanzomib.Investigational
DelaprilThe serum concentration of Tianeptine can be increased when it is combined with Delapril.Experimental
DesmopressinThe risk or severity of adverse effects can be increased when Tianeptine is combined with Desmopressin.Approved
DexmedetomidineTianeptine may decrease the antihypertensive activities of Dexmedetomidine.Approved, Vet Approved
DexmethylphenidateThe risk or severity of adverse effects can be increased when Dexmethylphenidate is combined with Tianeptine.Approved, Investigational
DextroamphetamineTianeptine may increase the stimulatory activities of Dextroamphetamine.Approved, Illicit
DicoumarolTianeptine may increase the anticoagulant activities of Dicoumarol.Approved
DiethylpropionTianeptine may increase the stimulatory activities of Diethylpropion.Approved, Illicit
DihydroergotamineTianeptine may decrease the antihypertensive activities of Dihydroergotamine.Approved, Investigational
DiphenadioneTianeptine may increase the anticoagulant activities of Diphenadione.Experimental
DipivefrinTianeptine may decrease the antihypertensive activities of Dipivefrin.Approved
DobutamineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Dobutamine.Approved
DoxofyllineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Doxofylline.Approved, Investigational
DroxidopaTianeptine may decrease the antihypertensive activities of Droxidopa.Approved, Investigational
DuloxetineDuloxetine may increase the serotonergic activities of Tianeptine.Approved
EcabetThe serum concentration of Tianeptine can be increased when it is combined with Ecabet.Approved, Investigational
EdoxabanThe serum concentration of Tianeptine can be increased when it is combined with Edoxaban.Approved
ElafinThe serum concentration of Tianeptine can be increased when it is combined with Elafin.Investigational
EnalaprilThe serum concentration of Tianeptine can be increased when it is combined with Enalapril.Approved, Vet Approved
EnalaprilatThe serum concentration of Tianeptine can be increased when it is combined with Enalaprilat.Approved
EnalkirenThe serum concentration of Tianeptine can be increased when it is combined with Enalkiren.Experimental
EphedraTianeptine may decrease the antihypertensive activities of Ephedra.Approved, Nutraceutical, Withdrawn
Epigallocatechin GallateThe serum concentration of Tianeptine can be increased when it is combined with Epigallocatechin Gallate.Investigational
EpinephrineTianeptine may decrease the antihypertensive activities of Epinephrine.Approved, Vet Approved
ErgotamineTianeptine may decrease the antihypertensive activities of Ergotamine.Approved
EscitalopramThe risk or severity of adverse effects can be increased when Tianeptine is combined with Escitalopram.Approved, Investigational
Ethyl biscoumacetateTianeptine may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
EtomidateTianeptine may decrease the antihypertensive activities of Etomidate.Approved
FaldaprevirThe serum concentration of Tianeptine can be increased when it is combined with Faldaprevir.Investigational
FenoterolThe risk or severity of adverse effects can be increased when Tianeptine is combined with Fenoterol.Approved, Investigational
FluindioneTianeptine may increase the anticoagulant activities of Fluindione.Approved, Investigational
FluoxetineThe risk or severity of adverse effects can be increased when Fluoxetine is combined with Tianeptine.Approved, Vet Approved
FluvoxamineThe risk or severity of adverse effects can be increased when Fluvoxamine is combined with Tianeptine.Approved, Investigational
FormoterolThe risk or severity of adverse effects can be increased when Tianeptine is combined with Formoterol.Approved, Investigational
FosamprenavirThe serum concentration of Tianeptine can be increased when it is combined with Fosamprenavir.Approved
FosinoprilThe serum concentration of Tianeptine can be increased when it is combined with Fosinopril.Approved
FurazolidoneThe risk or severity of adverse effects can be increased when Tianeptine is combined with Furazolidone.Approved, Investigational, Vet Approved
GabexateThe serum concentration of Tianeptine can be increased when it is combined with Gabexate.Investigational
GeldanamycinThe serum concentration of Tianeptine can be increased when it is combined with Geldanamycin.Experimental, Investigational
GepefrineTianeptine may increase the stimulatory activities of Gepefrine.Experimental
GM6001The serum concentration of Tianeptine can be increased when it is combined with GM6001.Experimental
GuanabenzTianeptine may decrease the antihypertensive activities of Guanabenz.Approved, Investigational
GuanfacineTianeptine may decrease the antihypertensive activities of Guanfacine.Approved, Investigational
HarmalineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Harmaline.Experimental
HexobarbitalThe metabolism of Tianeptine can be increased when combined with Hexobarbital.Approved
HydracarbazineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Hydracarbazine.Experimental
HydroxyamphetamineTianeptine may increase the stimulatory activities of Hydroxyamphetamine.Approved
IdraparinuxThe serum concentration of Tianeptine can be increased when it is combined with Idraparinux.Investigational
ImidaprilThe serum concentration of Tianeptine can be increased when it is combined with Imidapril.Investigational
IndacaterolThe risk or severity of adverse effects can be increased when Tianeptine is combined with Indacaterol.Approved
IndinavirThe serum concentration of Tianeptine can be increased when it is combined with Indinavir.Approved
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Tianeptine.Approved, Investigational
Iofetamine I-123Tianeptine may increase the stimulatory activities of Iofetamine I-123.Approved
IproclozideThe risk or severity of adverse effects can be increased when Tianeptine is combined with Iproclozide.Withdrawn
IproniazidThe risk or severity of adverse effects can be increased when Tianeptine is combined with Iproniazid.Withdrawn
IsocarboxazidThe risk or severity of adverse effects can be increased when Tianeptine is combined with Isocarboxazid.Approved
IsoetarineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Isoetarine.Approved
IsoflurophateThe serum concentration of Tianeptine can be increased when it is combined with Isoflurophate.Approved, Investigational, Withdrawn
IsoprenalineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Isoprenaline.Approved, Investigational
IxazomibThe serum concentration of Tianeptine can be increased when it is combined with Ixazomib.Approved, Investigational
LepirudinThe serum concentration of Tianeptine can be increased when it is combined with Lepirudin.Approved
LetaxabanThe serum concentration of Tianeptine can be increased when it is combined with Letaxaban.Investigational
LevonordefrinTianeptine may decrease the antihypertensive activities of Levonordefrin.Approved
LevosalbutamolThe risk or severity of adverse effects can be increased when Tianeptine is combined with Levosalbutamol.Approved, Investigational
LevothyroxineLevothyroxine may increase the arrhythmogenic activities of Tianeptine.Approved
LinagliptinThe serum concentration of Tianeptine can be increased when it is combined with Linagliptin.Approved
LinezolidLinezolid may increase the serotonergic activities of Tianeptine.Approved, Investigational
LiothyronineLiothyronine may increase the arrhythmogenic activities of Tianeptine.Approved, Vet Approved
LiotrixLiotrix may increase the arrhythmogenic activities of Tianeptine.Approved
LisdexamfetamineTianeptine may increase the stimulatory activities of Lisdexamfetamine.Approved, Investigational
LisinoprilThe serum concentration of Tianeptine can be increased when it is combined with Lisinopril.Approved, Investigational
LithiumLithium may increase the neurotoxic activities of Tianeptine.Approved
LofexidineTianeptine may decrease the antihypertensive activities of Lofexidine.Approved, Investigational
LopinavirThe serum concentration of Tianeptine can be increased when it is combined with Lopinavir.Approved
LorpiprazoleThe serum concentration of Tianeptine can be increased when it is combined with Lorpiprazole.Approved
MebanazineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Mebanazine.Withdrawn
MelagatranThe serum concentration of Tianeptine can be increased when it is combined with Melagatran.Experimental
MephedroneTianeptine may increase the stimulatory activities of Mephedrone.Investigational
MephentermineTianeptine may increase the vasopressor activities of Mephentermine.Approved
MetaraminolTianeptine may increase the vasopressor activities of Metaraminol.Approved, Investigational
MethamphetamineTianeptine may decrease the antihypertensive activities of Methamphetamine.Approved, Illicit
MethohexitalThe metabolism of Tianeptine can be increased when combined with Methohexital.Approved
MethoxamineTianeptine may increase the vasopressor activities of Methoxamine.Approved, Investigational
MethoxyphenamineTianeptine may increase the stimulatory activities of Methoxyphenamine.Experimental
Methylene blueTianeptine may increase the serotonergic activities of Methylene blue.Approved, Investigational
MethylphenidateThe risk or severity of adverse effects can be increased when Methylphenidate is combined with Tianeptine.Approved, Investigational
MethylphenobarbitalThe metabolism of Tianeptine can be increased when combined with Methylphenobarbital.Approved
MetoclopramideThe risk or severity of adverse effects can be increased when Metoclopramide is combined with Tianeptine.Approved, Investigational
MetyrosineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Tianeptine.Approved
MidodrineTianeptine may increase the vasopressor activities of Midodrine.Approved
MidomafetamineTianeptine may increase the stimulatory activities of Midomafetamine.Experimental, Illicit, Investigational
MinaprineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Minaprine.Approved
MMDATianeptine may increase the stimulatory activities of MMDA.Experimental, Illicit
MoclobemideThe risk or severity of adverse effects can be increased when Tianeptine is combined with Moclobemide.Approved, Investigational
MoexiprilThe serum concentration of Tianeptine can be increased when it is combined with Moexipril.Approved
MoxonidineThe therapeutic efficacy of Moxonidine can be decreased when used in combination with Tianeptine.Approved, Investigational
N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-ProlineThe serum concentration of Tianeptine can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Experimental
NafamostatThe serum concentration of Tianeptine can be increased when it is combined with Nafamostat.Approved, Investigational
NaphazolineTianeptine may decrease the antihypertensive activities of Naphazoline.Approved
NelfinavirThe serum concentration of Tianeptine can be increased when it is combined with Nelfinavir.Approved
NialamideThe risk or severity of adverse effects can be increased when Tianeptine is combined with Nialamide.Withdrawn
NicorandilTianeptine may increase the hypotensive activities of Nicorandil.Approved, Investigational
NitroaspirinThe serum concentration of Tianeptine can be increased when it is combined with Nitroaspirin.Investigational
NorepinephrineTianeptine may decrease the antihypertensive activities of Norepinephrine.Approved
OctamoxinThe risk or severity of adverse effects can be increased when Tianeptine is combined with Octamoxin.Withdrawn
OlodaterolThe risk or severity of adverse effects can be increased when Tianeptine is combined with Olodaterol.Approved
OmapatrilatThe serum concentration of Tianeptine can be increased when it is combined with Omapatrilat.Investigational
OrciprenalineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Orciprenaline.Approved
OtamixabanThe serum concentration of Tianeptine can be increased when it is combined with Otamixaban.Investigational
OxymetazolineTianeptine may decrease the antihypertensive activities of Oxymetazoline.Approved, Investigational
PaliperidoneTianeptine may decrease the antihypertensive activities of Paliperidone.Approved
PargylineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Pargyline.Approved
ParoxetineThe risk or severity of adverse effects can be increased when Paroxetine is combined with Tianeptine.Approved, Investigational
PentobarbitalThe metabolism of Tianeptine can be increased when combined with Pentobarbital.Approved, Investigational, Vet Approved
PergolideTianeptine may decrease the antihypertensive activities of Pergolide.Approved, Investigational, Vet Approved, Withdrawn
PerindoprilThe serum concentration of Tianeptine can be increased when it is combined with Perindopril.Approved
PhenelzineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Phenelzine.Approved
PhenindioneTianeptine may increase the anticoagulant activities of Phenindione.Approved, Investigational
PheniprazineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Pheniprazine.Withdrawn
PhenobarbitalThe metabolism of Tianeptine can be increased when combined with Phenobarbital.Approved, Investigational
PhenoxypropazineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Phenoxypropazine.Withdrawn
PhenprocoumonTianeptine may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
PhentermineTianeptine may increase the stimulatory activities of Phentermine.Approved, Illicit
PhenylephrineTianeptine may increase the vasopressor activities of Phenylephrine.Approved
PhenylpropanolamineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Phenylpropanolamine.Approved, Vet Approved, Withdrawn
PhosphoramidonThe serum concentration of Tianeptine can be increased when it is combined with Phosphoramidon.Experimental
PirbuterolThe risk or severity of adverse effects can be increased when Tianeptine is combined with Pirbuterol.Approved
PirlindoleThe risk or severity of adverse effects can be increased when Tianeptine is combined with Pirlindole.Approved
PitolisantThe therapeutic efficacy of Pitolisant can be decreased when used in combination with Tianeptine.Approved, Investigational
PivhydrazineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Pivhydrazine.Withdrawn
PrimidoneThe metabolism of Tianeptine can be increased when combined with Primidone.Approved, Vet Approved
PrinomastatThe serum concentration of Tianeptine can be increased when it is combined with Prinomastat.Investigational
ProcarbazineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Procarbazine.Approved, Investigational
ProcaterolThe risk or severity of adverse effects can be increased when Tianeptine is combined with Procaterol.Approved, Investigational
ProtokylolThe risk or severity of adverse effects can be increased when Tianeptine is combined with Protokylol.Approved, Vet Approved
PseudoephedrineTianeptine may decrease the antihypertensive activities of Pseudoephedrine.Approved
QuinaprilThe serum concentration of Tianeptine can be increased when it is combined with Quinapril.Approved, Investigational
QuinidineTianeptine may increase the QTc-prolonging activities of Quinidine.Approved, Investigational
RacecadotrilThe serum concentration of Tianeptine can be increased when it is combined with Racecadotril.Investigational
RacepinephrineTianeptine may decrease the antihypertensive activities of Racepinephrine.Approved
RamiprilThe serum concentration of Tianeptine can be increased when it is combined with Ramipril.Approved
RasagilineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Rasagiline.Approved
RemikirenThe serum concentration of Tianeptine can be increased when it is combined with Remikiren.Approved
RisperidoneTianeptine may decrease the antihypertensive activities of Risperidone.Approved, Investigational
RitobegronTianeptine may increase the stimulatory activities of Ritobegron.Investigational
RitodrineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Ritodrine.Approved, Investigational
RitonavirThe serum concentration of Tianeptine can be increased when it is combined with Ritonavir.Approved, Investigational
RivaroxabanThe serum concentration of Tianeptine can be increased when it is combined with Rivaroxaban.Approved
RopiniroleTianeptine may decrease the antihypertensive activities of Ropinirole.Approved, Investigational
S-3304The serum concentration of Tianeptine can be increased when it is combined with S-3304.Investigational
SafrazineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Safrazine.Withdrawn
SalbutamolThe risk or severity of adverse effects can be increased when Tianeptine is combined with Salbutamol.Approved, Vet Approved
SalmeterolThe risk or severity of adverse effects can be increased when Tianeptine is combined with Salmeterol.Approved
SaquinavirThe serum concentration of Tianeptine can be increased when it is combined with Saquinavir.Approved, Investigational
SaxagliptinThe serum concentration of Tianeptine can be increased when it is combined with Saxagliptin.Approved
SecobarbitalThe metabolism of Tianeptine can be increased when combined with Secobarbital.Approved, Vet Approved
SelegilineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Selegiline.Approved, Investigational, Vet Approved
SertralineThe risk or severity of adverse effects can be increased when Sertraline is combined with Tianeptine.Approved
SimeprevirThe serum concentration of Tianeptine can be increased when it is combined with Simeprevir.Approved
SitagliptinThe serum concentration of Tianeptine can be increased when it is combined with Sitagliptin.Approved, Investigational
SivelestatThe serum concentration of Tianeptine can be increased when it is combined with Sivelestat.Investigational
Sodium phosphateThe risk or severity of adverse effects can be increased when Tianeptine is combined with Sodium phosphate.Approved
SpiraprilThe serum concentration of Tianeptine can be increased when it is combined with Spirapril.Approved
St. John's WortThe metabolism of Tianeptine can be increased when combined with St. John's Wort.Approved, Investigational, Nutraceutical
TelaprevirThe serum concentration of Tianeptine can be increased when it is combined with Telaprevir.Approved, Withdrawn
TemocaprilThe serum concentration of Tianeptine can be increased when it is combined with Temocapril.Experimental, Investigational
TerbinafineThe metabolism of Tianeptine can be decreased when combined with Terbinafine.Approved, Investigational, Vet Approved
TerbutalineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Terbutaline.Approved
ThiamylalThe metabolism of Tianeptine can be increased when combined with Thiamylal.Approved, Vet Approved
ThiopentalThe metabolism of Tianeptine can be increased when combined with Thiopental.Approved, Vet Approved
ThiorphanThe serum concentration of Tianeptine can be increased when it is combined with Thiorphan.Experimental
Thyroid, porcineThyroid, porcine may increase the arrhythmogenic activities of Tianeptine.Approved
TioclomarolTianeptine may increase the anticoagulant activities of Tioclomarol.Experimental
TipranavirThe serum concentration of Tianeptine can be increased when it is combined with Tipranavir.Approved, Investigational
TizanidineTianeptine may decrease the antihypertensive activities of Tizanidine.Approved, Investigational
ToloxatoneThe risk or severity of adverse effects can be increased when Tianeptine is combined with Toloxatone.Approved
TramadolTianeptine may increase the neuroexcitatory activities of Tramadol.Approved, Investigational
TrandolaprilThe serum concentration of Tianeptine can be increased when it is combined with Trandolapril.Approved
TranylcypromineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Tranylcypromine.Approved, Investigational
UbenimexThe serum concentration of Tianeptine can be increased when it is combined with Ubenimex.Experimental, Investigational
UlinastatinThe serum concentration of Tianeptine can be increased when it is combined with Ulinastatin.Investigational
Valproic AcidThe serum concentration of Tianeptine can be increased when it is combined with Valproic Acid.Approved, Investigational
VemurafenibThe risk or severity of QTc prolongation can be increased when Vemurafenib is combined with Tianeptine.Approved
VilanterolThe risk or severity of adverse effects can be increased when Tianeptine is combined with Vilanterol.Approved
VildagliptinThe serum concentration of Tianeptine can be increased when it is combined with Vildagliptin.Approved, Investigational
WarfarinTianeptine may increase the anticoagulant activities of Warfarin.Approved
XimelagatranThe serum concentration of Tianeptine can be increased when it is combined with Ximelagatran.Approved, Investigational, Withdrawn
XylazineTianeptine may decrease the antihypertensive activities of Xylazine.Vet Approved
XylometazolineTianeptine may decrease the antihypertensive activities of Xylometazoline.Approved, Investigational
YohimbineThe serum concentration of Yohimbine can be increased when it is combined with Tianeptine.Approved, Investigational, Vet Approved
Z-Val-Ala-Asp fluoromethyl ketoneThe serum concentration of Tianeptine can be increased when it is combined with Z-Val-Ala-Asp fluoromethyl ketone.Experimental
ZofenoprilThe serum concentration of Tianeptine can be increased when it is combined with Zofenopril.Experimental
Food Interactions
Not Available

References

General References
  1. Wilde MI, Benfield P: Tianeptine. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in depression and coexisting anxiety and depression. Drugs. 1995 Mar;49(3):411-39. [PubMed:7774514]
  2. Kole MH, Swan L, Fuchs E: The antidepressant tianeptine persistently modulates glutamate receptor currents of the hippocampal CA3 commissural associational synapse in chronically stressed rats. Eur J Neurosci. 2002 Sep;16(5):807-16. [PubMed:12372016]
  3. Sohn W, Lee OY, Kwon JG, Park KS, Lim YJ, Kim TH, Jung SW, Kim JI: Tianeptine vs amitriptyline for the treatment of irritable bowel syndrome with diarrhea: a multicenter, open-label, non-inferiority, randomized controlled study. Neurogastroenterol Motil. 2012 Sep;24(9):860-e398. doi: 10.1111/j.1365-2982.2012.01945.x. Epub 2012 Jun 11. [PubMed:22679908]
  4. Reagan LP, Hendry RM, Reznikov LR, Piroli GG, Wood GE, McEwen BS, Grillo CA: Tianeptine increases brain-derived neurotrophic factor expression in the rat amygdala. Eur J Pharmacol. 2007 Jun 22;565(1-3):68-75. doi: 10.1016/j.ejphar.2007.02.023. Epub 2007 Feb 20. [PubMed:17368617]
  5. Delbende C, Contesse V, Mocaer E, Kamoun A, Vaudry H: The novel antidepressant, tianeptine, reduces stress-evoked stimulation of the hypothalamo-pituitary-adrenal axis. Eur J Pharmacol. 1991 Sep 24;202(3):391-6. [PubMed:1660816]
  6. Cooper CM, Whiting DA, Cowen PJ, Harmer CJ: Tianeptine in an experimental medicine model of antidepressant action. J Psychopharmacol. 2015 May;29(5):582-90. doi: 10.1177/0269881115573810. Epub 2015 Mar 10. [PubMed:25759404]
  7. Fromenty B, Freneaux E, Labbe G, Deschamps D, Larrey D, Letteron P, Pessayre D: Tianeptine, a new tricyclic antidepressant metabolized by beta-oxidation of its heptanoic side chain, inhibits the mitochondrial oxidation of medium and short chain fatty acids in mice. Biochem Pharmacol. 1989 Nov 1;38(21):3743-51. [PubMed:2597170]
  8. Grislain L, Gele P, Bertrand M, Luijten W, Bromet N, Salvadori C, Kamoun A: The metabolic pathways of tianeptine, a new antidepressant, in healthy volunteers. Drug Metab Dispos. 1990 Sep-Oct;18(5):804-8. [PubMed:1981739]
  9. 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. [PubMed:2341111]
  10. Szafarz M, Wencel A, Pociecha K, Fedak FA, Wlaz P, Wyska E: Pharmacokinetic study of tianeptine and its active metabolite MC5 in rats following different routes of administration using a novel liquid chromatography tandem mass spectrometry analytical method. Naunyn Schmiedebergs Arch Pharmacol. 2018 Feb;391(2):185-196. doi: 10.1007/s00210-017-1448-2. Epub 2017 Dec 12. [PubMed:29230490]
  11. Tianeptine [Link]
  12. Tianeptine [Link]
  13. Tianeptine properties [Link]
  14. The neurobiological properties of Tianeptine (Stablon): from monoamine hypothesis to glutamatergic modulation [Link]
  15. Pharmacokinetic study of tianeptine and its active metabolite MC5 in rats following different routes of administration using a novel liquid chromatography tandem mass spectrometry analytical method [Link]
  16. Effects of tianeptine on symptoms of fibromyalgia via BDNF signaling in a fibromyalgia animal model [Link]
  17. Anxiety- rather than depression-like behavior is associated with adult neurogenesis in a female mouse model of higher trait anxiety- and comorbid depression-like behavior [Link]
  18. Antidepressants: Past, Present and Future [Link]
  19. TIANEPTINE DRUG INFORMATION [Link]
  20. Acute Toxicity From Intravenous Use of the Tricyclic Antidepressant Tianeptine [Link]
  21. Management of Respiratory Depression from Tianeptine Overdose with Naloxone [Link]
External Links
Human Metabolome Database
HMDB0042038
KEGG Drug
D02575
PubChem Compound
68870
PubChem Substance
310265181
ChemSpider
62102
ChEBI
91749
ChEMBL
CHEMBL1289110
Wikipedia
Tianeptine
ATC Codes
N06AX14 — Tianeptine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3Unknown StatusTreatmentBipolar Disorder (BD)1
4CompletedTreatmentMajor Depressive Disorder (MDD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)148L1413
boiling point (°C)609.2L1413
Predicted Properties
PropertyValueSource
Water Solubility0.00413 mg/mLALOGPS
logP2.07ALOGPS
logP1.53ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)4.22ChemAxon
pKa (Strongest Basic)8.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area86.71 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity113.41 m3·mol-1ChemAxon
Polarizability45.73 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Fatty acids and conjugates
Direct Parent
Medium-chain fatty acids
Alternative Parents
Aralkylamines / Halogenated fatty acids / Heterocyclic fatty acids / Organosulfonamides / Aryl chlorides / Benzenoids / Amino acids / Dialkylamines / Carboxylic acids / Azacyclic compounds
show 6 more
Substituents
Medium-chain fatty acid / Halogenated fatty acid / Heterocyclic fatty acid / Aralkylamine / Aryl chloride / Aryl halide / Benzenoid / Organosulfonic acid amide / Organic sulfonic acid or derivatives / Organosulfonic acid or derivatives
show 21 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Serotonin:sodium symporter activity
Specific Function
Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into t...
Gene Name
SLC6A4
Uniprot ID
P31645
Uniprot Name
Sodium-dependent serotonin transporter
Molecular Weight
70324.165 Da
References
  1. Henry LK, Field JR, Adkins EM, Parnas ML, Vaughan RA, Zou MF, Newman AH, Blakely RD: Tyr-95 and Ile-172 in transmembrane segments 1 and 3 of human serotonin transporters interact to establish high affinity recognition of antidepressants. J Biol Chem. 2006 Jan 27;281(4):2012-23. Epub 2005 Nov 3. [PubMed:16272152]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...
Gene Name
HTR1A
Uniprot ID
P08908
Uniprot Name
5-hydroxytryptamine receptor 1A
Molecular Weight
46106.335 Da
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Pdz domain binding
Specific Function
Ionotropic glutamate receptor. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L-glutamate induces a co...
Gene Name
GRIA1
Uniprot ID
P42261
Uniprot Name
Glutamate receptor 1
Molecular Weight
101505.245 Da

Drug created on October 29, 2015 13:44 / Updated on March 02, 2018 05:24