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
Molecular Formula | C13H19NO |
Molecular Weight | 205.2961 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
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 |
---|---|---|
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
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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Diethylpropion and paranoid psychosis. | 1979 Mar |
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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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WHO Expert Committee on Drug Dependence. Thirty-second report. | 2001 |
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Long-term pharmacotherapy of obesity 2000: a review of efficacy and safety. | 2001 Aug 13-27 |
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[Uneasiness about the safety of bupropion as an aid to smoking cessation unjustified]. | 2001 Oct 20 |
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WHO Expert Committee on Drug Dependence. | 2003 |
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Obesity. | 2003 Dec |
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Effects of diethylpropion treatment and withdrawal on aorta reactivity, endothelial factors and rat behavior. | 2003 Jul 15 |
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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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Primary pulmonary hypertension after amfepramone (diethylpropion) with BMPR2 mutation. | 2003 Sep |
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Obesity: an overview on its current perspectives and treatment options. | 2004 Apr 14 |
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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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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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Amfepramone does not cause primary pulmonary hypertension. | 2004 May |
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[Pharmacotherapy of obesity]. | 2004 Oct 7 |
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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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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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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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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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Abuse liability and safety of oral lisdexamfetamine dimesylate in individuals with a history of stimulant abuse. | 2009 Jun |
|
The sirenomelia sequence: a case history. | 2010 |
|
A new method for the simultaneous determination of 1,4-benzodiazepines and amfepramone as adulterants in phytotherapeutic formulations by voltammetry. | 2010 Oct 10 |
Patents
Substance Class |
Chemical
Created
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Record UNII |
Q94YYU22B8
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Record Status |
Validated (UNII)
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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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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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ENANTIOMER -> RACEMATE |
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ENANTIOMER -> RACEMATE |
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
Norpseudoephedrine is a major metabolite of diethylpropion in man under acidic urine conditions.
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METABOLITE ACTIVE -> PRODRUG |
Dopamine: uptake IC50= 1014 +/- 80 nM, release IC50= >1000 nM; Norepinephrine: uptake IC50= 360 +/- 29 nM, release IC50= 99.3 +/- 6.6 nM; Serotonin: uptake IC50= 3840 +/- 240 nM, release IC50= 2118 +/- 98 nM
IN-VITRO
IC50
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