General
Preferred name
FENPROPOREX
Synonyms
Fenorex ()
Femproporex ()
J268.797F ()
P&D ID
PD009480
CAS
15686-61-0
16397-28-7
Tags
drug
Drug Status
illicit
investigational
withdrawn
experimental
approved
Max Phase
2.0
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
INDICATION Fenproporex is used as an appetite suppressant, and anti-obesity agent [2]; however, due to substance abuse potential, it is an illicit substance in many countries. In some countries, such as Brazil, it is still prescribed -- often in the form of diet pills (ie. Brazilian Diet Pills) which combine amphetamines, benzodiazepines, antidepressants, diuretics and laxatives. ; ; In the United States the sale of such diet pills has been banned due to concerns over side effects, and the risk of potentially fatal overdose.; However, internet sales and illicit markets has lead to international availability. It has been found by primary care physicians that Brazilian immigrant women utilized imported diet pills at particularly high rates, and sometimes suffered from side effects requiring hospitalization or experienced a loss of employment. [3]
MOA Fenproporex is an amphetamine based anorectic which is rapidly metabolized into amphetamine in the body. Both acute and chronic fenproporex administration has been shown to increase brain energy metabolism in young rats, by increasing the activity of citrate synthase, malate dehydrogenase, succinate dehydrogenase, creatine kinase and complexes I,II, III, and IV. [8]; ; Amphetamine based drugs are also known to reduce food intake. They are addictive substances due to their ability to increase dopamine release, however their anorectic effects are believed to be a result of noradrenergic neurotransmission. Activation of the alpha 1 and beta 2 adrenoceptors has been shown to decrease food intake, and drugs which release norepinephrine or block norepinephrine reuptake can activate these receptors. [3] ; ; The alpha 1 and beta 2 adrenoceptors are noted to be clinically important receptors in weight regulation. [3]
METABOLISM A large portion, 60-80%, of fenproporex is rapidly converted into amphetamine. Besides amphetamine, and unchanged fenproporex, 14 other metabolites were identified from urine samples. ; ; Two interacting metabolic pathways are believed to exist. The major pathway is believed to involve ring-degradation by aromatic hydroxylation, methylation, and side chain degradation by N-dealkyation to form amphetamine. The minor pathway involves the beta-hydroxylation of amphetamine to form norephedrine. [6];
Compound Sets
5
ChEMBL Drugs
CHEMBL2105566
DrugBank
DB01550
DrugCentral
1161
DrugCentral Approved Drugs
1161
Withdrawn 2.0
DB01550
External IDs
22
Properties
(calculated by RDKit )
Molecular Weight
188.13
Hydrogen Bond Acceptors
2
Hydrogen Bond Donors
1
Rotatable Bonds
5
Ring Count
1
Aromatic Ring Count
1
cLogP
2.12
TPSA
35.82
Fraction CSP3
0.42
Chiral centers
1.0
Largest ring
6.0
QED
0.72
Structural alerts
0
No structural alerts detected
Custom attributes
(extracted from source data)
ATC
N
Source data