Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C13H19NO |
Molecular Weight | 205.2961 |
Optical Activity | ( + ) |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCN(CC)[C@@H](C)C(=O)C1=CC=CC=C1
InChI
InChIKey=XXEPPPIWZFICOJ-NSHDSACASA-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/t11-/m0/s1
Molecular Formula | C13H19NO |
Molecular Weight | 205.2961 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 |
|
The stereochemistry of carbonyl reduction of diethylpropion and related amino-ketones in man. | 1974 Dec 1 |
|
Cardiovascular effects of amphepramone. | 1978 Apr-Jun |
|
High-altitude pulmonary edema with primary pulmonary hypertension. | 1996 Jul |
|
WHO Expert Committee on Drug Dependence. Thirty-second report. | 2001 |
|
The safety and efficacy of pharmaceutical and herbal caffeine and ephedrine use as a weight loss agent. | 2001 Aug |
|
Progression rate of Chinese herb nephropathy: impact of Aristolochia fangchi ingested dose. | 2002 Mar |
|
WHO Expert Committee on Drug Dependence. | 2003 |
|
Obesity. | 2003 Dec |
|
Effects of diethylpropion treatment and withdrawal on aorta reactivity, endothelial factors and rat behavior. | 2003 Jul 15 |
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Primary pulmonary hypertension after amfepramone (diethylpropion) with BMPR2 mutation. | 2003 Sep |
|
Obesity: an overview on its current perspectives and treatment options. | 2004 Apr 14 |
|
Pharmacological and surgical treatment of obesity. | 2004 Jul |
|
[Pharmacotherapy of obesity]. | 2004 Oct 7 |
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Drug Insight: appetite suppressants. | 2005 Feb |
|
Anti-obesity drugs and neural circuits of feeding. | 2008 Apr |
|
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 |
|
Abuse liability and safety of oral lisdexamfetamine dimesylate in individuals with a history of stimulant abuse. | 2009 Jun |
|
Necrotising vasculitis of the skin associated with an herbal medicine containing amfepramone. | 2009 Jun |
|
Tackling obesity: new therapeutic agents for assisted weight loss. | 2010 Apr 26 |
|
The serotonin syndrome-the need for physician's awareness. | 2010 Aug 20 |
|
Long-term pharmacotherapy for obesity in elderly patients: a retrospective evaluation of medical records from a specialized obesity outpatient clinic. | 2010 Jun 1 |
Patents
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 09:46:54 GMT 2023
by
admin
on
Sat Dec 16 09:46:54 GMT 2023
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Record UNII |
I535TOV6LY
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Record Status |
Validated (UNII)
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Record Version |
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I535TOV6LY
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admin on Sat Dec 16 09:46:54 GMT 2023 , Edited by admin on Sat Dec 16 09:46:54 GMT 2023
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Related Record | Type | Details | ||
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RACEMATE -> ENANTIOMER |
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