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 |
|
Diethylpropion and psychosis. | 1988 Apr |
|
Transient ischemic attacks associated with amfepramone therapy: a case report. | 1993 Sep-Oct |
|
Clinical and oculographic response to Tenuate Dospan (diethylpropionate) in a patient with congenital nystagmus. | 2002 Jan |
|
Progression rate of Chinese herb nephropathy: impact of Aristolochia fangchi ingested dose. | 2002 Mar |
|
Primary pulmonary hypertension after amfepramone (diethylpropion) with BMPR2 mutation. | 2003 Sep |
|
Pharmacological and surgical treatment of obesity. | 2004 Jul |
|
Obesity. | 2004 Jun |
|
Amfepramone does not cause primary pulmonary hypertension. | 2004 May |
|
Pharmacotherapy for obesity. | 2005 |
|
Phentermine and anaesthesia. | 2005 Aug |
|
Non-paracetamol drug-induced fulminant hepatic failure among adults in Scotland. | 2005 Feb |
|
Obesity. | 2005 Jun |
|
Anti-obesity drugs and neural circuits of feeding. | 2008 Apr |
|
Obesity: pathophysiology and clinical management. | 2009 |
|
Diethylpropion produces psychostimulant and reward effects. | 2009 Feb |
|
Abuse liability and safety of oral lisdexamfetamine dimesylate in individuals with a history of stimulant abuse. | 2009 Jun |
|
Neurochemical and behavioral effects elicited by bupropion and diethylpropion in rats. | 2010 Jul 29 |
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
|
Record UNII |
I535TOV6LY
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
39648-49-2
Created by
admin on Sat Dec 16 09:46:54 GMT 2023 , Edited by admin on Sat Dec 16 09:46:54 GMT 2023
|
PRIMARY | |||
|
667427
Created by
admin on Sat Dec 16 09:46:54 GMT 2023 , Edited by admin on Sat Dec 16 09:46:54 GMT 2023
|
PRIMARY | |||
|
I535TOV6LY
Created by
admin on Sat Dec 16 09:46:54 GMT 2023 , Edited by admin on Sat Dec 16 09:46:54 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
RACEMATE -> ENANTIOMER |
|