NAV

Amineptine

Identification

Generic Name
Amineptine
DrugBank Accession Number
DB04836
Background

The Food and Drug Administration suspended the marketing authorisation for Survector in 1999 and France withdrew it from the market, however several developing countries continued to produce it up until 2005.

Type
Small Molecule
Groups
Illicit, Withdrawn
Structure
3D
Similar Structures
Weight
Average: 337.463
Monoisotopic: 337.204179113
Chemical Formula
C22H27NO2
Synonyms
  • Amineptine
  • Amineptino
  • Amineptinum
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Pharmacology

Indication

For the treatment of depression.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Amineptine is an atypical tricyclic antidepressant.

Mechanism of action

Amineptine selectively inhibits the reuptake of dopamine and to a lesser extent norepinephrine, thus exerting a powerful and fast-acting antidepressant effect.

TargetActionsOrganism
USodium-dependent noradrenaline transporterNot AvailableHumans
USodium-dependent serotonin transporterNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Hepatic.

Route of elimination

Not Available

Half-life

48 minutes for the parent drug and 2.5 hours for the metabolites.

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Amineptine is combined with 1,2-Benzodiazepine.
AcarboseAmineptine may decrease the hypoglycemic activities of Acarbose.
AcebutololAmineptine may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of gastrointestinal bleeding can be increased when Amineptine is combined with Aceclofenac.
AcemetacinThe risk or severity of gastrointestinal bleeding can be increased when Amineptine is combined with Acemetacin.
Food Interactions
  • Avoid alcohol.
  • Avoid St. John's Wort.
  • Limit caffeine intake.
  • Take with food. Food reduces irritation.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Amineptine hydrochlorideA5P604A12R30272-08-3VDPUXONTAVMIKZ-UHFFFAOYSA-N
International/Other Brands
Directim / Maneon / Neolior / Provector / Survector (Servier) / Viaspera

Categories

ATC Codes
N06AA19 — Amineptine
Drug Categories
Classification
Not classified
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
27T1I13L6G
CAS number
57574-09-1
InChI Key
ONNOFKFOZAJDHT-UHFFFAOYSA-N
InChI
InChI=1S/C22H27NO2/c24-21(25)13-3-1-2-8-16-23-22-19-11-6-4-9-17(19)14-15-18-10-5-7-12-20(18)22/h4-7,9-12,22-23H,1-3,8,13-16H2,(H,24,25)
IUPAC Name
7-({tricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}amino)heptanoic acid
SMILES
OC(=O)CCCCCCNC1C2=CC=CC=C2CCC2=CC=CC=C12

References

Synthesis Reference

Melen,C., Danree, B.and Poignant, J.C.; US.Patent 3,758,528; September 11,1973; assigned to Societe en nom Collectif Science Union et Cie; Societe Francaise de Recherche Medicale. Melen, C., Danree, B. and Poignant, J.C.; U.S. Patent 3,821,249; June 28, 1974; assigned to Societe en nom Collectif Science Union et Cie; Societe Francaise de Recherche Medicale.

US3758528
General References
  1. Vaugeois JM, Corera AT, Deslandes A, Costentin J: Although chemically related to amineptine, the antidepressant tianeptine is not a dopamine uptake inhibitor. Pharmacol Biochem Behav. 1999 Jun;63(2):285-90. [Article]
  2. Grupper C: [New iatrogenic acne: acne caused by amineptin (Survector)]. Ann Dermatol Venereol. 1988;115(11):1174-6. [Article]
  3. Thioly-Bensoussan D, Charpentier A, Triller R, Thioly F, Blanchet P, Tricoire N, Noury JY, Grupper C: [Iatrogenic acne caused by amineptin (Survector). Apropos of 8 cases]. Ann Dermatol Venereol. 1988;115(11):1177-80. [Article]
  4. Vexiau P, Gourmel B, Husson C, Castot A, Rybojad M, Julien R, Fiet J, Puissant A, Cathelineau G: [Severe lesions of acne type induced by chronic amineptin poisoning: apropos of 6 cases]. Ann Dermatol Venereol. 1988;115(11):1180-2. [Article]
  5. Teillac D, Weber MJ, Lowenstein W, de Prost Y: [Acne caused by Survector]. Ann Dermatol Venereol. 1988;115(11):1183-4. [Article]
KEGG Drug
D07335
PubChem Compound
34869
PubChem Substance
46509012
ChemSpider
32091
BindingDB
50292474
RxNav
17698
ChEBI
32499
ChEMBL
CHEMBL418995
ZINC
ZINC000002001740
Therapeutic Targets Database
DCL000340
Wikipedia
Amineptine

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)226-230Melen,C., Danree, B.and Poignant, J.C.; US.Patent 3,758,528; September 11,1973; assigned to Societe en nom Collectif Science Union et Cie; Societe Francaise de Recherche Medicale Melen, C., Danree, B. and Poignant, J.C.; U.S. Patent 3,821,249; June 28, 1974; assigned to Societe en nom Collectif Science Union et Cie; Societe Francaise de Recherche Medicale
Predicted Properties
PropertyValueSource
Water Solubility0.000305 mg/mLALOGPS
logP1.99ALOGPS
logP2.74Chemaxon
logS-6ALOGPS
pKa (Strongest Acidic)4.41Chemaxon
pKa (Strongest Basic)9.17Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area49.33 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity101.21 m3·mol-1Chemaxon
Polarizability39.7 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.927
Blood Brain Barrier+0.9384
Caco-2 permeable-0.5548
P-glycoprotein substrateNon-substrate0.5457
P-glycoprotein inhibitor INon-inhibitor0.9324
P-glycoprotein inhibitor IINon-inhibitor0.8538
Renal organic cation transporterNon-inhibitor0.6998
CYP450 2C9 substrateNon-substrate0.7559
CYP450 2D6 substrateNon-substrate0.7653
CYP450 3A4 substrateNon-substrate0.5897
CYP450 1A2 substrateNon-inhibitor0.5434
CYP450 2C9 inhibitorNon-inhibitor0.8792
CYP450 2D6 inhibitorNon-inhibitor0.7593
CYP450 2C19 inhibitorNon-inhibitor0.8446
CYP450 3A4 inhibitorNon-inhibitor0.7073
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9165
Ames testAMES toxic0.6805
CarcinogenicityNon-carcinogens0.8651
BiodegradationNot ready biodegradable0.7096
Rat acute toxicity2.9526 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9341
hERG inhibition (predictor II)Inhibitor0.6018
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00du-0309000000-e59e100c1e36e79761df
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0019000000-ebb555203f45e72278ee
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0901000000-318ec450a3b384c3d38d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0494000000-3dc2fe8611befde706ef
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0005-1900000000-658d6806b3b9e88af583
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-05mo-5964000000-0d62ed688e9cae2ea91d
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-199.871372
predicted
DarkChem Lite v0.1.0
[M-H]-178.33698
predicted
DeepCCS 1.0 (2019)
[M+H]+201.376572
predicted
DarkChem Lite v0.1.0
[M+H]+180.69496
predicted
DeepCCS 1.0 (2019)
[M+Na]+200.205572
predicted
DarkChem Lite v0.1.0
[M+Na]+186.78813
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Details1. Sodium-dependent noradrenaline transporter
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Norepinephrine:sodium symporter activity
Specific Function
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A2
Uniprot ID
P23975
Uniprot Name
Sodium-dependent noradrenaline transporter
Molecular Weight
69331.42 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Details2. Sodium-dependent serotonin transporter
Kind
Protein
Organism
Humans
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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Drug created at September 12, 2007 09:05 / Updated at November 03, 2023 23:50