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 Date-3.2849281E11 |
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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Diethylpropion and psychosis. | 1988 Apr |
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Enantioseparation of amfepramone (rac-diethylpropion): preparative separation of the enantiomers and enantioselective analysis. | 1999 |
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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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Long-term pharmacotherapy of obesity 2000: a review of efficacy and safety. | 2001 Aug 13-27 |
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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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Effects of amphetamine, dexfenfluramine, diazepam, and other pharmacological and dietary manipulations on food "seeking" and "taking" behavior in non-human primates. | 2001 Oct |
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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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Obesity. | 2003 Dec |
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Homeopathic products, not as innocent and safe as they seem? A case report. | 2004 Aug |
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Pharmacological and surgical treatment of obesity. | 2004 Jul |
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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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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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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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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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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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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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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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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
Created by
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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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PRIMARY | |||
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100000087197
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D004053
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PRIMARY | |||
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874
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PRIMARY | |||
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DB00937
Created by
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974
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SUB05417MIG
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AMFEPRAMONE
Created by
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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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PRIMARY | RxNorm | ||
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90-84-6
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m4415
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PRIMARY | Merck Index | ||
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3059
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PRIMARY |
METABOLITE (PARENT)
METABOLITE ACTIVE (PRODRUG)
SALT/SOLVATE (PARENT)
SUBSTANCE RECORD