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Identification
Name Diethylpropion
Accession Number DB00937 (APRD00919)
Type small molecule
Groups illicit, approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
alpha-Benzoyltriethylamine
alpha-Diethylaminopropiophenone
Amfepramone
Amfepramone HCL
Amfepramone Hydrochloride
Amfepramonum [INN-Latin]
Amphepramonum hydrochloride
Anfepramona [INN-Spanish]
DEA No. 1610
Diethylcathinone
Diethylpropion HCL
Diethylpropion Hydrochloride
Diethylpropione
Diethylpropione hydrochloride
First Prev Next Last
Salts Not Available
Brand names
Name Company
Adiposon
Amfepramon
Amfepramone
Amphepramon
Amphepramone
Anfamon
Anorex
Cegramine
Danylen
Derfon
Dobesin
Frekentine
Keramik
Keramin
Magrene
Moderatan
Modulor
Neobes
Nopropiophenone
Obesitex
Parabolin
Prefamone
Regenon
Regenon hydrochloride
Reginon
Silutin
Tenuate
Tenuate Dospan
Tenuate hydrochloride
Tepanil
Tepanil Ten-tab
Tylinal
First Prev Next Last
Brand mixtures Not Available
Categories
  • Appetite Depressants
  • Anorexigenic Agents
  • Stimulants
CAS number 134-80-5
Weight Average: 205.2961
Monoisotopic: 205.146664235
Chemical Formula C13H19NO
InChI Key InChIKey=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
Plain Text
IUPAC Name
2-(diethylamino)-1-phenylpropan-1-one
SMILES
CCN(CC)C(C)C(=O)C1=CC=CC=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenethylamines
  • Acetophenones and Derivatives
  • Amphetamines
Substructures
  • Amino Ketones
  • Benzene and Derivatives
  • Aliphatic and Aryl Amines
  • Phenethylamines
  • Aromatic compounds
  • Benzoyl Derivatives
  • Acetophenones and Derivatives
  • Amphetamines
  • Ketones
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.
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.
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
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
Form Route Strength
Tablet Oral
Tablet, extended release Oral
Prices
Unit description Cost Unit
Diethylpropion HCl CR 75 mg 24 Hour tablet 1.0 USD tablet
Tenuate 25 mg tablet 0.67 USD tablet
Diethylpropion 25 mg tablet 0.52 USD tablet
Diethylpropion HCl 25 mg tablet 0.29 USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
logP 2.8 Not Available
Predicted Properties
Property Value Source
water solubility 1.22e+00 g/l ALOGPS
logP 2.8 ALOGPS
logP 2.7 ChemAxon
logS -2.2 ALOGPS
pKa (strongest acidic) 17.43 ChemAxon
pKa (strongest basic) 7.44 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 0 ChemAxon
polar surface area 20.31 ChemAxon
rotatable bond count 5 ChemAxon
refractivity 63.88 ChemAxon
polarizability 24.12 ChemAxon
References
Synthesis Reference Not Available
General Reference
  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. Epub 2008 Mar 18. Pubmed
  2. Arias HR, Santamaria A, Ali SF: Pharmacological and neurotoxicological actions mediated by bupropion and diethylpropion. Int Rev Neurobiol. 2009;88:223-55. Pubmed
External Links
Resource Link
KEGG Compound C06954 Link_out
PubChem Compound 7029 Link_out
PubChem Substance 46506622 Link_out
ChemSpider 6762 Link_out
ChEBI 4530 Link_out
ChEMBL 4530 Link_out
Therapeutic Targets Database DAP001452 Link_out
PharmGKB PA164778098 Link_out
Drug Product Database 2047675 Link_out
RxList http://www.rxlist.com/cgi/generic3/diethprop.htm Link_out
Drugs.com http://www.drugs.com/cdi/diethylpropion.html Link_out
PDRhealth http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/ten1435.shtml Link_out
Wikipedia http://en.wikipedia.org/wiki/Diethylpropion Link_out
ATC Codes
  • A08AA03
AHFS Codes
  • 28:20.92
PDB Entries Not Available
FDA label show (114 KB)
MSDS show (103 KB)
Interactions
Drug Interactions
Drug Interaction
Acetophenazine Decreased anorexic effect, may increase psychotic symptoms
Chlorpromazine Decreased anorexic effect, may increase psychotic symptoms
Ethopropazine Decreased anorexic effect, may increase psychotic symptoms
Fluoxetine Risk of serotoninergic syndrome
Fluphenazine Decreased anorexic effect, may increase psychotic symptoms
Fluvoxamine Risk of serotoninergic syndrome
Guanethidine Diethylpropion may decrease the effect of guanethidine.
Isocarboxazid Possible hypertensive crisis
Mesoridazine Decreased anorexic effect, may increase psychotic symptoms
Methdilazine Decreased anorexic effect, may increase psychotic symptoms
Methotrimeprazine Decreased anorexic effect, may increase psychotic symptoms
Paroxetine Risk of serotoninergic syndrome
Perphenazine Decreased anorexic effect, may increase psychotic symptoms
Phenelzine Possible hypertensive crisis
Prochlorperazine Decreased anorexic effect, may increase psychotic symptoms.
Promazine Decreased anorexic effect, may increase psychotic symptoms
Promethazine Decreased anorexic effect, may increase psychotic symptoms.
Propericiazine Decreased anorexic effect, may increase psychotic symptoms.
Propiomazine Decreased anorexic effect, may increase psychotic symptoms
Rasagiline Possible hypertensive crisis
Thiethylperazine Decreased anorexic effect, may increase psychotic symptoms
Thioridazine Decreased anorexic effect, may increase psychotic symptoms
Tranylcypromine Possible hypertensive crisis
Trifluoperazine Decreased anorexic effect, may increase psychotic symptoms
Triflupromazine Decreased anorexic effect, may increase psychotic symptoms
Trimeprazine Decreased anorexic effect, may increase psychotic symptoms
Venlafaxine Risk of serotoninergic syndrome
Food Interactions
  • Take without regard to meals.
Targets

1. Sodium-dependent noradrenaline transporter

Pharmacological action: yes
Actions: inhibitor

Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals

Organism class: human
UniProt ID: P23975 Link_out
Gene: SLC6A2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
  3. Arias HR, Santamaria A, Ali SF: Pharmacological and neurotoxicological actions mediated by bupropion and diethylpropion. Int Rev Neurobiol. 2009;88:223-55. Pubmed

2. Sodium-dependent dopamine transporter

Pharmacological action: yes
Actions: inhibitor

Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals

Organism class: human
UniProt ID: Q01959 Link_out
Gene: SLC6A3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  2. Arias HR, Santamaria A, Ali SF: Pharmacological and neurotoxicological actions mediated by bupropion and diethylpropion. Int Rev Neurobiol. 2009;88:223-55. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19