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Identification
NameAmineptine
Accession NumberDB04836
Typesmall molecule
Groupsillicit, withdrawn
Description

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.

Structure
Thumb
SynonymsNot Available
Salts
Name/CAS Structure Properties
Amineptine hydrochloride
Thumb
  • InChI Key: VDPUXONTAVMIKZ-UHFFFAOYSA-N
  • Monoisotopic Mass: 373.180856852
  • Average Mass: 373.916
DBSALT000803
Brand names
NameCompany
DirectimNot Available
ManeonNot Available
NeoliorNot Available
ProvectorNot Available
SurvectorServier
ViasperaNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number57574-09-1
WeightAverage: 373.916
Monoisotopic: 373.180856852
Chemical FormulaC22H28ClNO2
InChI KeyVDPUXONTAVMIKZ-UHFFFAOYSA-N
InChI
InChI=1S/C22H27NO2.ClH/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);1H
IUPAC Name
N-(6-carboxyhexyl)tricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-aminium chloride
SMILES
[Cl-].OC(=O)CCCCCC[NH2+]C1C2=CC=CC=C2CCC2=CC=CC=C12
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassDibenzocycloheptenes
SubclassNot Available
Direct parentDibenzocycloheptenes
Alternative parentsCarbocyclic Fatty Acids; Benzene and Substituted Derivatives; Carboxylic Acids; Enolates; Polyamines
Substituentsbenzene; carboxylic acid derivative; polyamine; enolate; carboxylic acid; amine; organonitrogen compound
Classification descriptionThis compound belongs to the dibenzocycloheptenes. These are compounds containing a dibenzocycloheptene moiety, which consists of two benzene connected by a cycloheptene ring.
Pharmacology
IndicationFor the treatment of depression.
PharmacodynamicsAmineptine is an atypical tricyclic antidepressant.
Mechanism of actionAmineptine selectively inhibits the reuptake of dopamine and to a lesser extent norepinephrine, thus exerting a powerful and fast-acting antidepressant effect.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic.

Route of eliminationNot Available
Half life48 minutes for the parent drug and 2.5 hours for the metabolites.
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.927
Blood Brain Barrier + 0.9384
Caco-2 permeable - 0.5548
P-glycoprotein substrate Non-substrate 0.5457
P-glycoprotein inhibitor I Non-inhibitor 0.9324
P-glycoprotein inhibitor II Non-inhibitor 0.8538
Renal organic cation transporter Non-inhibitor 0.6998
CYP450 2C9 substrate Non-substrate 0.7559
CYP450 2D6 substrate Non-substrate 0.7653
CYP450 3A4 substrate Non-substrate 0.5897
CYP450 1A2 substrate Non-inhibitor 0.5434
CYP450 2C9 substrate Non-inhibitor 0.8792
CYP450 2D6 substrate Non-inhibitor 0.7593
CYP450 2C19 substrate Non-inhibitor 0.8446
CYP450 3A4 substrate Non-inhibitor 0.7073
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9165
Ames test AMES toxic 0.6805
Carcinogenicity Non-carcinogens 0.8651
Biodegradation Not ready biodegradable 0.7096
Rat acute toxicity 2.9526 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9341
hERG inhibition (predictor II) Inhibitor 0.6018
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point226-230Melen,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 solubility1.84e-05 g/lALOGPS
logP0.99ALOGPS
logP2.74ChemAxon
logS-7.3ALOGPS
pKa (strongest acidic)4.41ChemAxon
pKa (strongest basic)9.46ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count2ChemAxon
polar surface area53.91ChemAxon
rotatable bond count8ChemAxon
refractivity112.63ChemAxon
polarizability39.95ChemAxon
number of rings3ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleYesChemAxon
Spectra
SpectraNot Available
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 Reference
  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. Pubmed
  2. Grupper C: [New iatrogenic acne: acne caused by amineptin (Survector)] Ann Dermatol Venereol. 1988;115(11):1174-6. Pubmed
  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. Pubmed
  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. Pubmed
  5. Teillac D, Weber MJ, Lowenstein W, de Prost Y: [Acne caused by Survector] Ann Dermatol Venereol. 1988;115(11):1183-4. Pubmed
External Links
ResourceLink
PubChem Compound34869
PubChem Substance46509012
ChemSpider32090
ChEBI32499
ChEMBL
Therapeutic Targets DatabaseDCL000340
WikipediaAmineptine
ATC CodesN06AA19
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Sodium-dependent noradrenaline transporter

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Sodium-dependent noradrenaline transporter P23975 Details

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. Pubmed
  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. Pubmed

2. Sodium-dependent serotonin transporter

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Sodium-dependent serotonin transporter P31645 Details

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. Pubmed
  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. Pubmed

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Drug created on September 12, 2007 03:05 / Updated on March 27, 2014 14:24