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 |
|---|---|---|---|
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 |
|---|---|---|
| A new method for the simultaneous determination of 1,4-benzodiazepines and amfepramone as adulterants in phytotherapeutic formulations by voltammetry. | 2010-10-10 |
|
| The serotonin syndrome-the need for physician's awareness. | 2010-08-20 |
|
| Neurochemical and behavioral effects elicited by bupropion and diethylpropion in rats. | 2010-07-29 |
|
| Long-term pharmacotherapy for obesity in elderly patients: a retrospective evaluation of medical records from a specialized obesity outpatient clinic. | 2010-06-01 |
|
| Tackling obesity: new therapeutic agents for assisted weight loss. | 2010-04-26 |
|
| Clinical and economic considerations of antiobesity treatment: a review of orlistat. | 2010 |
|
| The sirenomelia sequence: a case history. | 2010 |
|
| A randomized double-blind placebo-controlled study of the long-term efficacy and safety of diethylpropion in the treatment of obese subjects. | 2009-08 |
|
| Abuse liability and safety of oral lisdexamfetamine dimesylate in individuals with a history of stimulant abuse. | 2009-06 |
|
| Necrotising vasculitis of the skin associated with an herbal medicine containing amfepramone. | 2009-06 |
|
| Diethylpropion produces psychostimulant and reward effects. | 2009-02 |
|
| Update on the management of attention-deficit/hyperactivity disorder in children and adults: patient considerations and the role of lisdexamfetamine. | 2009 |
|
| Pharmacological and neurotoxicological actions mediated by bupropion and diethylpropion. | 2009 |
|
| Obesity: pathophysiology and clinical management. | 2009 |
|
| Anti-obesity drugs and neural circuits of feeding. | 2008-04 |
|
| Rimonabant: the evidence for its use in the treatment of obesity and the metabolic syndrome. | 2008-02-29 |
|
| Maternal fluoxetine treatment decreases behavioral response to dopaminergic drugs in female pups. | 2007-11-26 |
|
| Weight loss medications--where do they fit in? | 2006-08 |
|
| [Drug treatment of obesity]. | 2006-01-09 |
|
| Safety of drug therapies used for weight loss and treatment of obesity. | 2006 |
|
| Safety of obesity drugs. | 2005-11 |
|
| Phentermine and anaesthesia. | 2005-08 |
|
| Obesity. | 2005-06 |
|
| Meta-analysis: pharmacologic treatment of obesity. | 2005-04-05 |
|
| Serotonin1A-receptor antagonism blocks psychostimulant properties of diethylpropion in marmosets (Callithrix penicillata). | 2005-03-21 |
|
| Drug Insight: appetite suppressants. | 2005-02 |
|
| Non-paracetamol drug-induced fulminant hepatic failure among adults in Scotland. | 2005-02 |
|
| Pharmacotherapy for obesity. | 2005 |
|
| Diabesity: are weight loss medications effective? | 2005 |
|
| [Pharmacotherapy of obesity]. | 2004-10-07 |
|
| Homeopathic products, not as innocent and safe as they seem? A case report. | 2004-08 |
|
| Pharmacological and surgical treatment of obesity. | 2004-07 |
|
| Obesity. | 2004-06 |
|
| [Determination of fenfluramine, diethylpropion and mazindol in slimming foods by gas chromatography-mass spectrometry]. | 2004-05 |
|
| Amfepramone does not cause primary pulmonary hypertension. | 2004-05 |
|
| Obesity. | 2003-12 |
|
| Enantioseparation of amfepramone (rac-diethylpropion): preparative separation of the enantiomers and enantioselective analysis. | 1999 |
|
| 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 |
|
| Pupillary changes associated with the development of stimulant-induced mania: a case report. | 1997-06 |
|
| High-altitude pulmonary edema with primary pulmonary hypertension. | 1996-07 |
|
| Transient ischemic attacks associated with amfepramone therapy: a case report. | 1993-09-01 |
|
| Diethylpropion and psychosis. | 1988-04 |
|
| Diethylpropion and paranoid psychosis. | 1979-03 |
|
| A double-blind controlled study of the use of diethylpropion hydrochloride (Tenuate) in obese patients in a rural practice. | 1978-10-25 |
|
| Cardiovascular effects of amphepramone. | 1978-04-01 |
|
| Schizophrenia-like reaction to diethylpropion. | 1976-11-27 |
|
| The stereochemistry of carbonyl reduction of diethylpropion and related amino-ketones in man. | 1974-12-01 |
|
| Proceedings: Pharmacokinetic and stereo-chemical studies on diethylpropion and related compounds in man. | 1974-12 |
|
| Some chemical and stereochemical aspects of diethylpropion metabolism in man. | 1973-12 |
|
| Long-term use of diethylpropion in obesity. | 1973 |
Patents
| Substance Class |
Chemical
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admin
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| Record UNII |
Q94YYU22B8
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| Record Status |
Validated (UNII)
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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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| 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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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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