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Identification
NameChlorphentermine
Accession NumberDB01556
Typesmall molecule
Groupsexperimental, illicit, withdrawn
Description

A sympathomimetic agent that was formerly used as an anorectic. It has properties similar to those of dextroamphetamine. It has been implicated in lipid storage disorders and pulmonary hypertension. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1223)

Structure
Thumb
Synonyms
SynonymLanguageCode
4-Chloro-a,a-dimethylbenzeneethanamineNot AvailableNot Available
4-Chloro-a,a-dimethylphenethylamineNot AvailableNot Available
a,a-Dimethyl-p-chlorophenethylamineNot AvailableNot Available
ChlorphenterminumLatinNot Available
ClorfenterminaSpanishNot Available
Salts
Name/CAS Structure Properties
Chlorphentermine hydrochloride
Thumb
  • InChI Key: WEJDYJKJPUPMLH-UHFFFAOYSA-N
  • Monoisotopic Mass: 219.058154899
  • Average Mass: 220.139
DBSALT000815
Brand names
NameCompany
ApsedonNot Available
DesopimonNot Available
LucofenNot Available
Brand mixturesNot Available
Categories
CAS number461-78-9
WeightAverage: 183.678
Monoisotopic: 183.08147716
Chemical FormulaC10H14ClN
InChI KeyInChIKey=ZCKAMNXUHHNZLN-UHFFFAOYSA-N
InChI
InChI=1S/C10H14ClN/c1-10(2,12)7-8-3-5-9(11)6-4-8/h3-6H,7,12H2,1-2H3
IUPAC Name
1-(4-chlorophenyl)-2-methylpropan-2-amine
SMILES
CC(C)(N)CC1=CC=C(Cl)C=C1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassPhenethylamines
Direct parentAmphetamines and Derivatives
Alternative parentsChlorobenzenes; Aryl Chlorides; Polyamines; Organochlorides; Monoalkylamines
Substituentschlorobenzene; aryl halide; aryl chloride; polyamine; amine; organochloride; organohalogen; primary amine; primary aliphatic amine; organonitrogen compound
Classification descriptionThis compound belongs to the amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
Pharmacology
IndicationUsed as an appetite suppressant.
PharmacodynamicsChlorphentermine is a relatively weak stimulant with little abuse potential. It is no longer used due mainly to safety concerns, as it has a serotonergic effects profile similar to other withdrawn appetite suppressants such as fenfluramine and aminorex which were found to cause pulmonary hypertension and cardiac fibrosis following prolonged use.
Mechanism of actionNot Available
AbsorptionWell absorbed following oral administration.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half life40 hours
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9966
Blood Brain Barrier + 0.9792
Caco-2 permeable + 0.7531
P-glycoprotein substrate Non-substrate 0.6627
P-glycoprotein inhibitor I Non-inhibitor 0.9092
P-glycoprotein inhibitor II Non-inhibitor 0.9805
Renal organic cation transporter Non-inhibitor 0.8185
CYP450 2C9 substrate Non-substrate 0.8464
CYP450 2D6 substrate Substrate 0.5148
CYP450 3A4 substrate Non-substrate 0.5233
CYP450 1A2 substrate Inhibitor 0.6449
CYP450 2C9 substrate Non-inhibitor 0.8526
CYP450 2D6 substrate Inhibitor 0.8286
CYP450 2C19 substrate Non-inhibitor 0.752
CYP450 3A4 substrate Non-inhibitor 0.5737
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7748
Ames test Non AMES toxic 0.8728
Carcinogenicity Non-carcinogens 0.6055
Biodegradation Not ready biodegradable 0.9895
Rat acute toxicity 2.8974 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9818
hERG inhibition (predictor II) Non-inhibitor 0.738
Pharmacoeconomics
Manufacturers
  • Parke davis div warner lambert co
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
boiling point100-102 °C at 2.00E+00 mm HgNot Available
logP2.60HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility1.05e-01 g/lALOGPS
logP2.81ALOGPS
logP2.69ChemAxon
logS-3.2ALOGPS
pKa (strongest basic)10.24ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count1ChemAxon
hydrogen donor count1ChemAxon
polar surface area26.02ChemAxon
rotatable bond count2ChemAxon
refractivity53.15ChemAxon
polarizability20.19ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. GYLYS JA, HART JJ, WARREN MR: Chlorphentermine, a new anorectic agent. J Pharmacol Exp Ther. 1962 Sep;137:365-73. Pubmed
External Links
ResourceLink
KEGG CompoundC07559
PubChem Compound10007
PubChem Substance46505599
ChemSpider9613
WikipediaChlorphentermine
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
Comments
Drug created on July 31, 2007 07:10 / Updated on September 16, 2013 17:15