Details
Stereochemistry | RACEMIC |
Molecular Formula | C13H19NO |
Molecular Weight | 205.2961 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCN(CC)C(C)C(=O)C1=CC=CC=C1
InChI
InChIKey=XXEPPPIWZFICOJ-UHFFFAOYSA-N
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
DescriptionSources: https://tripod.nih.gov/ginas/app/substance/I535TOV6LYhttp://www.drugbank.ca/drugs/DB00937https://tripod.nih.gov/ginas/app/substance/P1A5AE6Q2RCurator's Comment: Description was created based on several sources, including
Sources: https://tripod.nih.gov/ginas/app/substance/I535TOV6LYhttp://www.drugbank.ca/drugs/DB00937https://tripod.nih.gov/ginas/app/substance/P1A5AE6Q2R
Curator's Comment: Description was created based on several sources, including
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. 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. It is 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.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19897080
Curator's Comment: exerts its effects in the brain in a similar manner to amphetamine, stimulating the release as well as inhibiting the reuptake of neurotransmitters such as DA, NE, and 5-HT
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL222 Sources: http://www.drugbank.ca/drugs/DB00937 |
|||
Target ID: CHEMBL238 Sources: http://www.drugbank.ca/drugs/DB00937 |
1.014 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | TENUATE Approved UseTENUATE and TENUATE DOSPAN are indicated in the management of exogenous obesity as
a short-term adjunct (a few weeks) in a regimen of weight reduction based on caloric restriction
in patients with an initial body mass index (BMI) of 30 kg/m2 or higher and who have not
responded to appropriate weight reducing regimen (diet and/or exercise) alone. Launch Date1959 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7.04 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31780765 |
75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIETHYLPROPION plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
36.59 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31780765 |
75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIETHYLPROPION plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.95 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31780765 |
75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIETHYLPROPION plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
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Sources: https://pmj.bmj.com/content/61/715/419.short Page: 420.0 |
PubMed
Title | Date | PubMed |
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Long-term use of diethylpropion in obesity. | 1973 |
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Some chemical and stereochemical aspects of diethylpropion metabolism in man. | 1973 Dec |
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Proceedings: Pharmacokinetic and stereo-chemical studies on diethylpropion and related compounds in man. | 1974 Dec |
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The stereochemistry of carbonyl reduction of diethylpropion and related amino-ketones in man. | 1974 Dec 1 |
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Schizophrenia-like reaction to diethylpropion. | 1976 Nov 27 |
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Cardiovascular effects of amphepramone. | 1978 Apr-Jun |
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A double-blind controlled study of the use of diethylpropion hydrochloride (Tenuate) in obese patients in a rural practice. | 1978 Oct 25 |
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Diethylpropion and paranoid psychosis. | 1979 Mar |
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Diethylpropion and psychosis. | 1988 Apr |
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Transient ischemic attacks associated with amfepramone therapy: a case report. | 1993 Sep-Oct |
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High-altitude pulmonary edema with primary pulmonary hypertension. | 1996 Jul |
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Pupillary changes associated with the development of stimulant-induced mania: a case report. | 1997 Jun |
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Kinetics of racemization of (+)- and (-)-diethylpropion: studies in aqueous solution, with and without the addition of cyclodextrins, in organic solvents and in human plasma. | 1998 |
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Enantioseparation of amfepramone (rac-diethylpropion): preparative separation of the enantiomers and enantioselective analysis. | 1999 |
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Bupropion for smokers. Drug is almost identical in structure to diethylpropion, a controlled drug. | 2001 Feb 17 |
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Clinical and oculographic response to Tenuate Dospan (diethylpropionate) in a patient with congenital nystagmus. | 2002 Jan |
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Obesity. | 2003 Dec |
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Obesity. | 2004 Jun |
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[Determination of fenfluramine, diethylpropion and mazindol in slimming foods by gas chromatography-mass spectrometry]. | 2004 May |
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Pharmacotherapy for obesity. | 2005 |
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Diabesity: are weight loss medications effective? | 2005 |
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Meta-analysis: pharmacologic treatment of obesity. | 2005 Apr 5 |
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Phentermine and anaesthesia. | 2005 Aug |
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Drug Insight: appetite suppressants. | 2005 Feb |
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Non-paracetamol drug-induced fulminant hepatic failure among adults in Scotland. | 2005 Feb |
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Obesity. | 2005 Jun |
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Safety of obesity drugs. | 2005 Nov |
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Safety of drug therapies used for weight loss and treatment of obesity. | 2006 |
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Weight loss medications--where do they fit in? | 2006 Aug |
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[Drug treatment of obesity]. | 2006 Jan 9 |
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Anti-obesity drugs and neural circuits of feeding. | 2008 Apr |
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Rimonabant: the evidence for its use in the treatment of obesity and the metabolic syndrome. | 2008 Feb 29 |
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Maternal fluoxetine treatment decreases behavioral response to dopaminergic drugs in female pups. | 2008 Nov-Dec |
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Update on the management of attention-deficit/hyperactivity disorder in children and adults: patient considerations and the role of lisdexamfetamine. | 2009 |
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Pharmacological and neurotoxicological actions mediated by bupropion and diethylpropion. | 2009 |
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Obesity: pathophysiology and clinical management. | 2009 |
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A randomized double-blind placebo-controlled study of the long-term efficacy and safety of diethylpropion in the treatment of obese subjects. | 2009 Aug |
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Diethylpropion produces psychostimulant and reward effects. | 2009 Feb |
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Abuse liability and safety of oral lisdexamfetamine dimesylate in individuals with a history of stimulant abuse. | 2009 Jun |
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Necrotising vasculitis of the skin associated with an herbal medicine containing amfepramone. | 2009 Jun |
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Clinical and economic considerations of antiobesity treatment: a review of orlistat. | 2010 |
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The sirenomelia sequence: a case history. | 2010 |
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Tackling obesity: new therapeutic agents for assisted weight loss. | 2010 Apr 26 |
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The serotonin syndrome-the need for physician's awareness. | 2010 Aug 20 |
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Neurochemical and behavioral effects elicited by bupropion and diethylpropion in rats. | 2010 Jul 29 |
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Long-term pharmacotherapy for obesity in elderly patients: a retrospective evaluation of medical records from a specialized obesity outpatient clinic. | 2010 Jun 1 |
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A new method for the simultaneous determination of 1,4-benzodiazepines and amfepramone as adulterants in phytotherapeutic formulations by voltammetry. | 2010 Oct 10 |
Patents
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Classification Tree | Code System | Code | ||
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DEA NO. |
1610
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NDF-RT |
N0000175423
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N0000175651
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WHO-ATC |
A08AA03
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NDF-RT |
N0000175372
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WHO-VATC |
QA08AA03
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NCI_THESAURUS |
C29728
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NDF-RT |
N0000175372
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NCI_THESAURUS |
C47795
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LIVERTOX |
NBK548787
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Code System | Code | Type | Description | ||
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CHEMBL1194666
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202-019-1
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4530
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Q94YYU22B8
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7161
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100000087197
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D004053
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874
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DB00937
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974
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SUB05417MIG
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AMFEPRAMONE
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Q94YYU22B8
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7029
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DTXSID6022929
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C61721
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3389
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90-84-6
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m4415
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3059
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PRIMARY |
METABOLITE (PARENT)
METABOLITE ACTIVE (PRODRUG)
SALT/SOLVATE (PARENT)
SUBSTANCE RECORD