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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GroupsIllicit, Withdrawn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
External Identifiers Not Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
DirectimNot Available
ManeonNot Available
NeoliorNot Available
ProvectorNot Available
SurvectorServier
ViasperaNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Amineptine hydrochloride
Thumb
  • InChI Key: VDPUXONTAVMIKZ-UHFFFAOYSA-N
  • Monoisotopic Mass: 373.180856852
  • Average Mass: 373.916
DBSALT000803
Categories
UNII27T1I13L6G
CAS number57574-09-1
WeightAverage: 373.916
Monoisotopic: 373.180856852
Chemical FormulaC22H28ClNO2
InChI KeyInChIKey=VDPUXONTAVMIKZ-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[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-2-aminium chloride
SMILES
[Cl-].OC(=O)CCCCCC[NH2+]C1C2=CC=CC=C2CCC2=CC=CC=C12
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as dibenzocycloheptenes. These are compounds containing a dibenzocycloheptene moiety, which consists of two benzene connected by a cycloheptene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassDibenzocycloheptenes
Sub ClassNot Available
Direct ParentDibenzocycloheptenes
Alternative Parents
Substituents
  • Dibenzocycloheptene
  • Carbocyclic fatty acid
  • Medium-chain fatty acid
  • Aralkylamine
  • Fatty acyl
  • Fatty acid
  • Quaternary ammonium salt
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic chloride salt
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Organic zwitterion
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
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.
Related Articles
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
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 )
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 mg/mLALOGPS
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 Area53.91 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity112.63 m3·mol-1ChemAxon
Polarizability39.95 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
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 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. [PubMed:10371658 ]
  2. Grupper C: [New iatrogenic acne: acne caused by amineptin (Survector)]. Ann Dermatol Venereol. 1988;115(11):1174-6. [PubMed:2977079 ]
  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:2977080 ]
  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:2977081 ]
  5. Teillac D, Weber MJ, Lowenstein W, de Prost Y: [Acne caused by Survector]. Ann Dermatol Venereol. 1988;115(11):1183-4. [PubMed:2977082 ]
External Links
ATC CodesN06AA19
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
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
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. [PubMed:17139284 ]
  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:17016423 ]
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 the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin an...
Gene Name:
SLC6A4
Uniprot ID:
P31645
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. [PubMed:17139284 ]
  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:17016423 ]
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Drug created on September 12, 2007 03:05 / Updated on March 27, 2014 14:24