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Identification
NameDiethylpropion
Accession NumberDB00937  (APRD00919)
TypeSmall Molecule
GroupsApproved, Illicit
Description

A appetite depressant considered to produce less central nervous system disturbance than most drugs in this therapeutic category. It is also considered to be among the safest for patients with hypertension. (From AMA Drug Evaluations Annual, 1994, p2290)

Structure
Thumb
Synonyms
(+-)-Diethylpropion
(±)-diethylpropion
1-phenyl-2-diethylamino-1-propanone
2-(Diethylamino)-1-phenyl-1-propanone
2-(Diethylamino)propiophenone
alpha-Benzoyltriethylamine
alpha-Diethylaminopropiophenone
Amfepramone
Amfepramonum
Anfepramona
Diethylcathinone
Diethylpropion
External Identifiers
  • DEA No. 1610
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Diethylpropion HCl Controlled-releasetablet75 mg/1oralActavis Pharma, Inc.1960-11-17Not applicableUs
Diethylpropion HCl Controlled-releasetablet75 mg/1oralPreferred Pharmaceuticals, Inc.2014-02-12Not applicableUs
Diethylpropion HCl Controlled-releasetablet75 mg/1oralA S Medication Solutions Llc1960-11-17Not applicableUs
Diethylpropion HCl Controlled-releasetablet75 mg/1oralbryant ranch prepack2008-01-01Not applicableUs
Diethylpropion HCl Controlled-releasetablet75 mg/1oralA S Medication Solutions Llc1960-11-17Not applicableUs
Diethylpropion HCl Controlled-releasetablet75 mg/1oralRebel Distributors Corp2008-01-01Not applicableUs
Diethylpropion HCl Controlled-releasetablet75 mg/1oralPhysicians Total Care, Inc.2005-10-03Not applicableUs
Diethylpropion HCl Immediate-releasetablet25 mg/1oralA S Medication Solutions Llc1959-08-06Not applicableUs
Diethylpropion HCl Immediate-releasetablet25 mg/1oralbryant ranch prepack2008-01-01Not applicableUs
Diethylpropion HCl Immediate-releasetablet25 mg/1oralA S Medication Solutions Llc1959-08-06Not applicableUs
Diethylpropion HCl Immediate-releasetablet25 mg/1oralActavis Pharma, Inc.1959-08-06Not applicableUs
Diethylpropion HCl Immediate-releasetablet25 mg/1oralPhysicians Total Care, Inc.2004-06-14Not applicableUs
Diethylpropion Hydrochloride Controlled-releasetablet75 mg/1oralPd Rx Pharmaceuticals, Inc.2008-01-01Not applicableUs
Nobesine 75 Sustained Release Capsule 75mgcapsule (sustained-release)75 mgoralRougier Pharma Division Of Ratiopharm Inc1978-12-311999-09-27Canada
Tenuatetablet25 mgoralSanofi Aventis Canada Inc1994-12-312009-03-24Canada
Tenuate Dospantablet (extended-release)75 mgoralSanofi Aventis Canada Inc1994-12-312009-01-31Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Diethylpropion HCl Controlled-releasetablet75 mg/1oralBlenheim Pharmacal, Inc.2010-03-30Not applicableUs
Diethylpropion HCl Controlled-releasetablet75 mg/1oralKeltman Pharmaceuticals Inc.2010-06-07Not applicableUs
Diethylpropion HCl Immediate-releasetablet25 mg/1oralPd Rx Pharmaceuticals, Inc.2008-01-01Not applicableUs
Diethylpropion HCl Immediate-releasetablet25 mg/1oralKeltman Pharmaceuticals Inc.2010-06-07Not applicableUs
Diethylpropion Hydrochloridetablet25 mg/1oralLannett Company, Inc.2011-07-18Not applicableUs
Diethylpropion Hydrochloridetablet25 mg/1oralAidarex Pharmaceuticals LLC2010-12-27Not applicableUs
Diethylpropion Hydrochloridetablet25 mg/1oralUnit Dose Services2010-12-27Not applicableUs
Diethylpropion Hydrochloridetablet25 mg/1oralA S Medication Solutions Llc2010-12-27Not applicableUs
Diethylpropion Hydrochloridetablet25 mg/1oralApotheca Inc1999-08-16Not applicableUs
Diethylpropion Hydrochloridetablet25 mg/1oralKvk Tech, Inc2010-12-27Not applicableUs
Diethylpropion Hydrochloridetablet25 mg/1oralPd Rx Pharmaceuticals, Inc.2010-12-27Not applicableUs
Diethylpropion Hydrochloridetablet25 mg/1oralCorepharma LLC.2008-11-062016-03-16Us
Diethylpropion Hydrochloride ERtablet75 mg/1oralApotheca Inc2008-10-23Not applicableUs
Diethylpropion Hydrochloride ERtablet, extended release75 mg/1oralA S Medication Solutions Llc2011-10-24Not applicableUs
Diethylpropion Hydrochloride ERtablet, extended release75 mg/1oralProficient Rx LP2011-10-24Not applicableUs
Diethylpropion Hydrochloride ERtablet, extended release75 mg/1oralPd Rx Pharmaceuticals, Inc.2011-10-24Not applicableUs
Diethylpropion Hydrochloride ERtablet, extended release75 mg/1oralPreferred Pharmaceuticals, Inc.2014-04-29Not applicableUs
Diethylpropion Hydrochloride ERtablet, extended release75 mg/1oralLannett Company, Inc.2011-10-24Not applicableUs
Diethylpropion Hydrochlorideer ERtablet, extended release75 mg/1oralAidarex Pharmaceuticals LLC2011-10-24Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AnorexNot Available
DobesinNot Available
FrekentineNot Available
LineaNot Available
ModeratanNot Available
NeobesMedix
NobesineNot Available
PrefamoneNot Available
RegenonTemmler
TepanilNot Available
TylinalNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Diethylpropion Hydrochloride
134-80-5
Thumb
  • InChI Key: ICFXZZFWRWNZMA-UHFFFAOYNA-N
  • Monoisotopic Mass: 241.123341974
  • Average Mass: 241.757
DBSALT000484
Categories
UNIIQ94YYU22B8
CAS number90-84-6
WeightAverage: 205.2961
Monoisotopic: 205.146664235
Chemical FormulaC13H19NO
InChI KeyInChIKey=XXEPPPIWZFICOJ-UHFFFAOYSA-N
InChI
InChI=1S/C13H19NO/c1-4-14(5-2)11(3)13(15)12-9-7-6-8-10-12/h6-11H,4-5H2,1-3H3
IUPAC Name
2-(diethylamino)-1-phenylpropan-1-one
SMILES
CCN(CC)C(C)C(=O)C1=CC=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as acetophenones. These are organic compounds containing the acetophenone structure.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAcetophenones
Direct ParentAcetophenones
Alternative Parents
Substituents
  • Phenylpropane
  • Acetophenone
  • Aryl alkyl ketone
  • Aryl ketone
  • Benzoyl
  • Alpha-aminoketone
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationUsed in the management of exogenous obesity as a short-term adjunct (a few weeks) in a regimen of weight reduction based on caloric restriction.
PharmacodynamicsDiethylpropion is a sympathomimetic stimulant drug marketed as an appetite suppressant. Chemically, it is the N,N-diethyl analog of cathinone. Its mechanism of action is similar to other appetite suppressants such as sibutramine, phentermine and dextroamphetamine.
Mechanism of actionDiethylpropion is an amphetamine that stimulates neurons to release or maintain high levels of a particular group of neurotransmitters known as catecholamines; these include dopamine and norepinephrine. High levels of these catecholamines tend to suppress hunger signals and appetite. Diethylpropion (through catecholamine elevation) may also indirectly affect leptin levels in the brain. It is theorized that diethylpropion can raise levels of leptin which signal satiety. It is also theorized that increased levels of the catecholamines are partially responsible for halting another chemical messenger known as neuropeptide Y. This peptide initiates eating, decreases energy expenditure, and increases fat storage.
Related Articles
AbsorptionDiethylpropion is rapidly absorbed from the GI tract after oral administration.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Extensively metabolized through a complex pathway of biotransformation involving N-dealkylation and reduction. Many of these metabolites are biologically active and may participate in the therapeutic action of diethylpropion.

Route of eliminationDiethylpropion is rapidly absorbed from the GI tract after oral administration and is extensively metabolized through a complex pathway of biotransformation involving N-dealkylation and reduction. Diethylpropion and/or its active metabolites are believed to cross the blood-brain barrier and the placenta. Diethylpropion and its metabolites are excreted mainly by the kidney.
Half lifeUsing a phosphorescence assay that is specific for basic compounds containing benzoyl group, the plasma half-life of the aminoketone metabolites is estimated to be between 4 to 6 hours.
ClearanceNot Available
ToxicityThe reported oral LD50 for mice is 600 mg/kg, for rats is 250 mg/kg and for dogs is 225 mg/kg. Manifestation of acute overdosage include restlessness, tremor, hyperreflexia, rapid respiration, confusion, assaultiveness, hallucinations, and panic states.
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+0.9354
Caco-2 permeable+0.8532
P-glycoprotein substrateNon-substrate0.5328
P-glycoprotein inhibitor INon-inhibitor0.8859
P-glycoprotein inhibitor IINon-inhibitor0.9157
Renal organic cation transporterNon-inhibitor0.6691
CYP450 2C9 substrateNon-substrate0.8022
CYP450 2D6 substrateNon-substrate0.6551
CYP450 3A4 substrateNon-substrate0.6339
CYP450 1A2 substrateInhibitor0.7358
CYP450 2C9 inhibitorNon-inhibitor0.952
CYP450 2D6 inhibitorNon-inhibitor0.7815
CYP450 2C19 inhibitorNon-inhibitor0.8088
CYP450 3A4 inhibitorNon-inhibitor0.9438
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6602
Ames testNon AMES toxic0.9326
CarcinogenicityCarcinogens 0.5877
BiodegradationNot ready biodegradable0.9236
Rat acute toxicity2.6791 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8475
hERG inhibition (predictor II)Non-inhibitor0.8179
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Sanofi aventis us llc
  • Watson pharmaceuticals
  • 3m pharmaceuticals inc
  • Corepharma llc
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Tg united labs llc
  • Ucb inc
  • Watson laboratories inc
Packagers
Dosage forms
FormRouteStrength
Tabletoral75 mg/1
Tabletoral25 mg/1
Tablet, extended releaseoral75 mg/1
Capsule (sustained-release)oral75 mg
Tabletoral25 mg
Tablet (extended-release)oral75 mg
Prices
Unit descriptionCostUnit
Diethylpropion HCl CR 75 mg 24 Hour tablet1.0USD tablet
Tenuate 25 mg tablet0.67USD tablet
Diethylpropion 25 mg tablet0.52USD tablet
Diethylpropion HCl 25 mg tablet0.29USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point168Schutte, J.; U.S. Patent 3,001,910; September 26, 1961; assigned to Firma Ternmler-Werke (W. Germany).
logP2.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.22 mg/mLALOGPS
logP2.8ALOGPS
logP2.7ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)17.43ChemAxon
pKa (Strongest Basic)7.44ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area20.31 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity63.88 m3·mol-1ChemAxon
Polarizability24.12 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
MSMass Spectrum (Electron Ionization)splash10-0udi-2900000000-43214c102b76f59ba4d1View in MoNA
References
Synthesis Reference

Schutte, J.; U.S. Patent 3,001,910; September 26, 1961; assigned to Firma Ternmler-Werke
(W. Germany).

US3001910
General References
  1. Adan RA, Vanderschuren LJ, la Fleur SE: Anti-obesity drugs and neural circuits of feeding. Trends Pharmacol Sci. 2008 Apr;29(4):208-17. doi: 10.1016/j.tips.2008.01.008. Epub 2008 Mar 18. [PubMed:18353447 ]
  2. Arias HR, Santamaria A, Ali SF: Pharmacological and neurotoxicological actions mediated by bupropion and diethylpropion. Int Rev Neurobiol. 2009;88:223-55. doi: 10.1016/S0074-7742(09)88009-4. [PubMed:19897080 ]
External Links
ATC CodesA08AA03
AHFS Codes
  • 28:20.92
PDB EntriesNot Available
FDA labelDownload (114 KB)
MSDSDownload (103 KB)
Interactions
Drug Interactions
Drug
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Diethylpropion.
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Diethylpropion.
AtomoxetineAtomoxetine may increase the hypertensive activities of Diethylpropion.
BenzphetamineThe risk or severity of adverse effects can be increased when Benzphetamine is combined with Diethylpropion.
ChlorphentermineThe risk or severity of adverse effects can be increased when Chlorphentermine is combined with Diethylpropion.
ClenbuterolThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Diethylpropion.
DobutamineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Diethylpropion.
DopamineThe risk or severity of adverse effects can be increased when Dopamine is combined with Diethylpropion.
DoxofyllineThe risk or severity of adverse effects can be increased when Diethylpropion is combined with Doxofylline.
DronabinolDronabinol may increase the tachycardic activities of Diethylpropion.
EpinephrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Diethylpropion.
EthanolThe risk or severity of adverse effects can be increased when Ethanol is combined with Diethylpropion.
FenoterolThe risk or severity of adverse effects can be increased when Fenoterol is combined with Diethylpropion.
FormoterolThe risk or severity of adverse effects can be increased when Formoterol is combined with Diethylpropion.
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Diethylpropion.
IsocarboxazidIsocarboxazid may increase the hypertensive activities of Diethylpropion.
IsoprenalineThe risk or severity of adverse effects can be increased when Isoprenaline is combined with Diethylpropion.
LabetalolThe risk or severity of adverse effects can be increased when Labetalol is combined with Diethylpropion.
LinezolidLinezolid may increase the hypertensive activities of Diethylpropion.
MephentermineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Diethylpropion.
MetaraminolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Diethylpropion.
MethamphetamineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Diethylpropion.
MethoxamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Diethylpropion.
MidodrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Diethylpropion.
MoclobemideMoclobemide may increase the hypertensive activities of Diethylpropion.
NaphazolineThe risk or severity of adverse effects can be increased when Naphazoline is combined with Diethylpropion.
NorepinephrineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Diethylpropion.
OrciprenalineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Diethylpropion.
OxymetazolineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Diethylpropion.
PhenelzinePhenelzine may increase the hypertensive activities of Diethylpropion.
PhenmetrazineThe risk or severity of adverse effects can be increased when Phenmetrazine is combined with Diethylpropion.
PhentermineThe risk or severity of adverse effects can be increased when Phentermine is combined with Diethylpropion.
PhenylephrineThe risk or severity of adverse effects can be increased when Phenylephrine is combined with Diethylpropion.
PhenylpropanolamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Diethylpropion.
ProcarbazineProcarbazine may increase the hypertensive activities of Diethylpropion.
RasagilineRasagiline may increase the hypertensive activities of Diethylpropion.
RitodrineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Diethylpropion.
SalmeterolThe risk or severity of adverse effects can be increased when Salmeterol is combined with Diethylpropion.
SelegilineSelegiline may increase the hypertensive activities of Diethylpropion.
Tedizolid PhosphateTedizolid Phosphate may increase the hypertensive activities of Diethylpropion.
TerbutalineThe risk or severity of adverse effects can be increased when Terbutaline is combined with Diethylpropion.
TranylcypromineTranylcypromine may increase the hypertensive activities of Diethylpropion.
Food Interactions
  • Take without regard to meals.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
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 ]
  3. Arias HR, Santamaria A, Ali SF: Pharmacological and neurotoxicological actions mediated by bupropion and diethylpropion. Int Rev Neurobiol. 2009;88:223-55. doi: 10.1016/S0074-7742(09)88009-4. [PubMed:19897080 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Monoamine transmembrane transporter activity
Specific Function:
Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A3
Uniprot ID:
Q01959
Molecular Weight:
68494.255 Da
References
  1. Yu H, Rothman RB, Dersch CM, Partilla JS, Rice KC: Uptake and release effects of diethylpropion and its metabolites with biogenic amine transporters. Bioorg Med Chem. 2000 Dec;8(12):2689-92. [PubMed:11131159 ]
  2. Arias HR, Santamaria A, Ali SF: Pharmacological and neurotoxicological actions mediated by bupropion and diethylpropion. Int Rev Neurobiol. 2009;88:223-55. doi: 10.1016/S0074-7742(09)88009-4. [PubMed:19897080 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on April 14, 2014 10:33