Identification

Name
Diethylpropion
Accession Number
DB00937  (APRD00919)
Type
Small Molecule
Groups
Approved, 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
  • 1-phenyl-2-diethylamino-1-propanone
  • 2-(diethylamino)-1-phenyl-1-propanone
  • 2-(diethylamino)propiophenone
  • alpha-Benzoyltriethylamine
  • alpha-Diethylaminopropiophenone
  • Amfepramone
  • Amfépramone
  • Amfepramonum
  • Anfepramona
  • Diethylcathinone
External IDs
DEA No. 1610
Product Ingredients
IngredientUNIICASInChI Key
Diethylpropion hydrochloride19V2PL39NG134-80-5ICFXZZFWRWNZMA-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Diethylpropion HCl Controlled-ReleaseTablet75 mg/1OralA S Medication Solutions1960-11-17Not applicableUs54569 039620180907 15195 bxqq0r
Diethylpropion HCl Controlled-ReleaseTablet75 mg/1OralActavis Pharma, Inc.1960-11-172019-06-30Us0591 078220180907 15195 i6scva
Diethylpropion HCl Controlled-ReleaseTablet75 mg/1OralNucare Pharmaceuticals, Inc.1960-11-17Not applicableUs
Diethylpropion HCl Controlled-ReleaseTablet75 mg/1OralA-S Medication Solutions1960-11-17Not applicableUs00591 0782 01 nlmimage10 fa45fd5f
Diethylpropion HCl Controlled-ReleaseTablet75 mg/1OralRebel Distributors2008-01-01Not applicableUs
Diethylpropion HCl Controlled-ReleaseTablet75 mg/1OralPreferreed Pharmaceuticals Inc.2014-02-12Not applicableUs68788 068620180913 8702 1dkszuz
Diethylpropion HCl Controlled-ReleaseTablet75 mg/1Oralbryant ranch prepack1960-11-17Not applicableUs63629 296720180907 15195 7fefut
Diethylpropion HCl Controlled-ReleaseTablet75 mg/1OralPhysicians Total Care, Inc.2005-10-03Not applicableUs54868 146320180907 15195 1pcd455
Diethylpropion HCl Immediate-ReleaseTablet25 mg/1Oralbryant ranch prepack1959-08-06Not applicableUs63629 401020180907 15195 jft4l5
Diethylpropion HCl Immediate-ReleaseTablet25 mg/1OralA-S Medication Solutions1959-08-06Not applicableUs50090 032620180913 8702 1oaeltc
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/1OralKeltman Pharmaceuticals Inc.2010-06-07Not applicableUs
Diethylpropion HydrochlorideTablet25 mg/1OralKvk Tech,Inc2010-12-27Not applicableUs
Diethylpropion HydrochlorideTablet25 mg/1OralNucare Pharmaceuticals, Inc.2011-07-18Not applicableUs
Diethylpropion HydrochlorideTablet25 mg/1OralA-S Medication Solutions2010-12-27Not applicableUs
Diethylpropion HydrochlorideTablet, extended release75 mg/1OralH.J. Harkins Company, Inc.2017-01-03Not applicableUs
Diethylpropion HydrochlorideTablet25 mg/1OralUnit Dose Services2010-12-27Not applicableUs
Diethylpropion HydrochlorideTablet25 mg/1Oralbryant ranch prepack2011-07-18Not applicableUs
Diethylpropion HydrochlorideTablet25 mg/1OralA-S Medication Solutions2011-07-18Not applicableUs
International/Other Brands
Anorex / Dobesin / Frekentine / Linea / Moderatan / Neobes (Medix) / Nobesine / Prefamone / Regenon (Temmler) / Tepanil / Tylinal
Categories
UNII
Q94YYU22B8
CAS number
90-84-6
Weight
Average: 205.2961
Monoisotopic: 205.146664235
Chemical Formula
C13H19NO
InChI Key
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

Pharmacology

Indication

Used in the management of exogenous obesity as a short-term adjunct (a few weeks) in a regimen of weight reduction based on caloric restriction.

Associated Conditions
Pharmacodynamics

Diethylpropion 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 action

Diethylpropion 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.

TargetActionsOrganism
ASodium-dependent noradrenaline transporter
inhibitor
Human
ASodium-dependent dopamine transporter
inhibitor
Human
Absorption

Diethylpropion is rapidly absorbed from the GI tract after oral administration.

Volume of distribution
Not Available
Protein binding
Not 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 elimination

Diethylpropion 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 life

Using 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.

Clearance
Not Available
Toxicity

The 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
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of serotonin syndrome can be increased when Diethylpropion is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of serotonin syndrome can be increased when Diethylpropion is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3-isobutyl-1-methyl-7H-xanthineThe risk or severity of adverse effects can be increased when Diethylpropion is combined with 3-isobutyl-1-methyl-7H-xanthine.
3,4-MethylenedioxyamphetamineThe risk or severity of serotonin syndrome can be increased when Diethylpropion is combined with 3,4-Methylenedioxyamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of serotonin syndrome can be increased when Diethylpropion is combined with 4-Bromo-2,5-dimethoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of serotonin syndrome can be increased when Diethylpropion is combined with 5-methoxy-N,N-dimethyltryptamine.
6-O-benzylguanineThe risk or severity of adverse effects can be increased when Diethylpropion is combined with 6-O-benzylguanine.
7-DeazaguanineThe risk or severity of adverse effects can be increased when Diethylpropion is combined with 7-Deazaguanine.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of serotonin syndrome can be increased when Diethylpropion is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
7,9-DimethylguanineThe risk or severity of adverse effects can be increased when Diethylpropion is combined with 7,9-Dimethylguanine.
Food Interactions
  • Take without regard to meals.

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
Human Metabolome Database
HMDB0015072
KEGG Drug
D07444
KEGG Compound
C06954
PubChem Compound
7029
PubChem Substance
46506622
ChemSpider
6762
ChEBI
4530
ChEMBL
CHEMBL1194666
Therapeutic Targets Database
DAP001452
PharmGKB
PA164778098
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Diethylpropion
ATC Codes
A08AA03 — Amfepramone
FDA label
Download (114 KB)
MSDS
Download (103 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2RecruitingTreatmentHeart Failure, Unspecified1
4TerminatedTreatmentBMI >30 kg/m21

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
  • Aidarex Pharmacuticals LLC
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Bryant Ranch Prepack
  • Calvin Scott and Co. Inc.
  • Carlisle Laboratories Inc.
  • Corepharma LLC
  • Darby Dental Supply Co. Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Keltman Pharmaceuticals Inc.
  • Lake Erie Medical and Surgical Supply
  • Landmark Chemical Co.
  • Macnary Ltd.
  • Merrell Pharmaceuticals Inc.
  • Nucare Pharmaceuticals Inc.
  • Patheon Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepak Systems Inc.
  • Qualitest
  • Quality Research Pharmaceutical Inc.
  • Rebel Distributors Corp.
  • Southwood Pharmaceuticals
  • United Research Laboratories Inc.
  • Watson Pharmaceuticals
Dosage forms
FormRouteStrength
TabletOral75 mg/1
TabletOral25 mg/1
Capsule, extended releaseOral75 mg
TabletOral25 mg
Tablet, extended releaseOral75 mg
Tablet, extended releaseOral75 mg/1
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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)168Schutte, 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 RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0udi-9600000000-6ee5a640521355e9e385
Mass Spectrum (Electron Ionization)MSsplash10-0udi-2900000000-43214c102b76f59ba4d1
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbonyl compounds
Direct Parent
Alkyl-phenylketones
Alternative Parents
Phenylpropanes / Benzoyl derivatives / Aryl alkyl ketones / Alpha-amino ketones / Trialkylamines / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Alkyl-phenylketone / Phenylpropane / Benzoyl / Aryl alkyl ketone / Benzenoid / Monocyclic benzene moiety / Alpha-aminoketone / Tertiary aliphatic amine / Tertiary amine / Hydrocarbon derivative
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
tertiary amine, aromatic ketone (CHEBI:4530)

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
Uniprot Name
Sodium-dependent noradrenaline transporter
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
Uniprot Name
Sodium-dependent dopamine transporter
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]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 08:39