Details
Stereochemistry | RACEMIC |
Molecular Formula | C13H19NO.ClH |
Molecular Weight | 241.757 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CCN(CC)C(C)C(=O)C1=CC=CC=C1
InChI
InChIKey=ICFXZZFWRWNZMA-UHFFFAOYSA-N
InChI=1S/C13H19NO.ClH/c1-4-14(5-2)11(3)13(15)12-9-7-6-8-10-12;/h6-11H,4-5H2,1-3H3;1H
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 |
---|---|---|
Some chemical and stereochemical aspects of diethylpropion metabolism in man. | 1973 Dec |
|
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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A double-blind controlled study of the use of diethylpropion hydrochloride (Tenuate) in obese patients in a rural practice. | 1978 Oct 25 |
|
Transient ischemic attacks associated with amfepramone therapy: a case report. | 1993 Sep-Oct |
|
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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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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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 |
|
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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[Uneasiness about the safety of bupropion as an aid to smoking cessation unjustified]. | 2001 Oct 20 |
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Clinical and oculographic response to Tenuate Dospan (diethylpropionate) in a patient with congenital nystagmus. | 2002 Jan |
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Progression rate of Chinese herb nephropathy: impact of Aristolochia fangchi ingested dose. | 2002 Mar |
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Obesity. | 2003 Dec |
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Treatment of obesity: an update on anti-obesity medications. | 2003 Feb |
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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. | 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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Phentermine and anaesthesia. | 2005 Aug |
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Non-paracetamol drug-induced fulminant hepatic failure among adults in Scotland. | 2005 Feb |
|
Weight loss medications--where do they fit in? | 2006 Aug |
|
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 |
|
Diethylpropion produces psychostimulant and reward effects. | 2009 Feb |
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Clinical and economic considerations of antiobesity treatment: a review of orlistat. | 2010 |
|
Neurochemical and behavioral effects elicited by bupropion and diethylpropion in rats. | 2010 Jul 29 |
|
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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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C29728
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NCI_THESAURUS |
C47795
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134-80-5
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1194009
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C47486
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205-156-5
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SUB00434MIG
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CHEMBL1194666
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DTXSID4047838
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643703
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m4415
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100000085421
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91442
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19V2PL39NG
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19V2PL39NG
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DBSALT000484
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81998
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PRIMARY | RxNorm |
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD