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 |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
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 |
---|---|---|
Long-term use of diethylpropion in obesity. | 1973 |
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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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Pupillary changes associated with the development of stimulant-induced mania: a case report. | 1997 Jun |
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WHO Expert Committee on Drug Dependence. Thirty-second report. | 2001 |
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The safety and efficacy of pharmaceutical and herbal caffeine and ephedrine use as a weight loss agent. | 2001 Aug |
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Clinical and oculographic response to Tenuate Dospan (diethylpropionate) in a patient with congenital nystagmus. | 2002 Jan |
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Neurotoxicity of diethylpropion: neurochemical and behavioral findings in rats. | 2002 Jun |
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Progression rate of Chinese herb nephropathy: impact of Aristolochia fangchi ingested dose. | 2002 Mar |
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WHO Expert Committee on Drug Dependence. | 2003 |
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Treatment of obesity: an update on anti-obesity medications. | 2003 Feb |
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High prevalence of fenfluramine-related aortic regurgitation in women with end-stage renal disease secondary to Chinese herb nephropathy. | 2003 May |
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[Determination of fenfluramine, diethylpropion and mazindol in slimming foods by gas chromatography-mass spectrometry]. | 2004 May |
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Amfepramone does not cause primary pulmonary hypertension. | 2004 May |
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[Pharmacotherapy of obesity]. | 2004 Oct 7 |
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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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Non-paracetamol drug-induced fulminant hepatic failure among adults in Scotland. | 2005 Feb |
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Obesity. | 2005 Jun |
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Serotonin1A-receptor antagonism blocks psychostimulant properties of diethylpropion in marmosets (Callithrix penicillata). | 2005 Mar 21 |
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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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Maternal fluoxetine treatment decreases behavioral response to dopaminergic drugs in female pups. | 2008 Nov-Dec |
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Obesity: pathophysiology and clinical management. | 2009 |
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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 |
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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NDF-RT |
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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METABOLITE (PARENT)
METABOLITE ACTIVE (PRODRUG)
SALT/SOLVATE (PARENT)
SUBSTANCE RECORD