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Identification
NameFencamfamine
Accession NumberDB01463
TypeSmall Molecule
GroupsApproved, Illicit, Withdrawn
Description

Fencamfamine (Glucoenergan, Reactivan) is a stimulant which was developed in the 1960s as an appetite suppressant, but was later withdrawn for this application due to problems with dependence and abuse. It is around half the potency of dexamphetamine, and is prescribed at a dose of 10-60mg, although abusers of the drug tend to rapidly develop tolerance and escalate their dose. Reactivan is still rarely used for treating depressive day-time fatigue, lack of concentration and lethargy, particularly in individuals who have chronic medical conditions, as its favourable safety profile makes it the most suitable drug in some cases. [Wikipedia]

Structure
Thumb
Synonyms
SynonymLanguageCode
FencamfaminNot AvailableNot Available
FencamfamineFrenchINN
FencamfaminumLatinINN
FencanfaminaSpanishINN
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
GlucoenerganNot Available
ReactivanNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Fencamfamine hydrochloride
Thumb
  • InChI Key: CVFSMSTXULJISA-UHFFFAOYNA-N
  • Monoisotopic Mass: 251.144077416
  • Average Mass: 251.795
DBSALT000814
Categories
CAS number1209-98-9
WeightAverage: 215.3339
Monoisotopic: 215.167399677
Chemical FormulaC15H21N
InChI KeyIKFBPFGUINLYQI-UHFFFAOYSA-N
InChI
InChI=1S/C15H21N/c1-2-16-15-13-9-8-12(10-13)14(15)11-6-4-3-5-7-11/h3-7,12-16H,2,8-10H2,1H3
IUPAC Name
N-ethyl-3-phenylbicyclo[2.2.1]heptan-2-amine
SMILES
CCNC1C2CCC(C2)C1C1=CC=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentBicyclic monoterpenoids
Alternative Parents
Substituents
  • Bicyclic monoterpenoid
  • Aromatic monoterpenoid
  • Aralkylamine
  • Cyclohexylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the the treatment of depressive fatigue in convalescence and other debilitated states as well as in the treatment of depressive day-time fatigue, lack of concentration and lethargy.
PharmacodynamicsFencamfamine increases drive and mental alertness and an elevation of mood and a general feeling of well-being. It is a central nervous system stimulant, which increases locomotor activity.
Mechanism of actionFencamfamine acts as an indirect dopamine agonist. It releases dopamine by a similar mechanism to amphetamines, but is 10x less potent than dexamphetamine at producing this effect. The drug seems to inhibit the dopamine transporter (DAT) that removes dopamine from the synapses. This inhibition of DAT blocks the reuptake of dopamine and norepinephrine into the presynaptic neuron, increasing the amount of dopamine in the synapse. It also stimulates the release of dopamine and norepinephrine into the synapse. Finally, it increases the magnitude of dopamine release after a stimulus, increasing the salience of stimulus. Also unlike amphetamines, fencamfamine does not inhibit the action of monoamine oxidase enzymes and so is somewhat safer. Some experiments also suggest a role for opioid receptors in the activity of fencamfamine, as low doses can cause paradoxical sedation, and some effects of the drug are blocked by naloxone.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityOverdosage is characterised by nausea, agitation and restlessness, dryness of the mouth, dizziness and tremor. In gross overdosage the above symptoms may also be associated with dyspnoea, tachycardia, disorientation and convulsions.
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+1.0
Blood Brain Barrier+0.9756
Caco-2 permeable+0.6244
P-glycoprotein substrateNon-substrate0.648
P-glycoprotein inhibitor IInhibitor0.5239
P-glycoprotein inhibitor IIInhibitor0.6499
Renal organic cation transporterNon-inhibitor0.5876
CYP450 2C9 substrateNon-substrate0.7441
CYP450 2D6 substrateNon-substrate0.6052
CYP450 3A4 substrateNon-substrate0.6348
CYP450 1A2 substrateInhibitor0.871
CYP450 2C9 substrateNon-inhibitor0.6742
CYP450 2D6 substrateInhibitor0.7272
CYP450 2C19 substrateInhibitor0.645
CYP450 3A4 substrateNon-inhibitor0.7812
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8237
Ames testNon AMES toxic0.7967
CarcinogenicityNon-carcinogens0.7716
BiodegradationNot ready biodegradable0.6553
Rat acute toxicity3.3827 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7712
hERG inhibition (predictor II)Inhibitor0.5827
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP3.20SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.00295 mg/mLALOGPS
logP3.46ALOGPS
logP3.21ChemAxon
logS-4.9ALOGPS
pKa (Strongest Basic)10.56ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity67.64 m3·mol-1ChemAxon
Polarizability26.13 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 ReferenceNot Available
General Reference
  1. Link
  2. DeLucia R, Planeta CS: Fencamfamine. Gen Pharmacol. 1990;21(2):161-3. Pubmed
External Links
ATC CodesN06BA06
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Sodium-dependent dopamine transporter

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Sodium-dependent dopamine transporter Q01959 Details

References:

  1. Seyfried CA: Dopamine uptake inhibiting versus dopamine releasing properties of fencamfamine: an in vitro study. Biochem Pharmacol. 1983 Aug 1;32(15):2329-31. Pubmed
  2. Li SM, Campbell BL, Katz JL: Interactions of cocaine with dopamine uptake inhibitors or dopamine releasers in rats discriminating cocaine. J Pharmacol Exp Ther. 2006 Jun;317(3):1088-96. Epub 2006 Feb 14. Pubmed

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Drug created on July 31, 2007 07:09 / Updated on September 16, 2013 17:14