CHEBI:439329 - (S)-fenfluramine

ChEBI IDCHEBI:439329
ChEBI Name(S)-fenfluramine
Stars
ASCII Name(S)-fenfluramine
DefinitionThe S-enantiomer of fenfluramine. It stimulates the release of serotonin and selectively inhibits its reuptake, but unlike fenfluramine it does not possess catecholamine agonist activity. It was formerly given by mouth as the hydrochloride in the treatment of obesity, but, like fenfluramine, was withdrawn wolrdwide following reports of valvular heart defects.
Last Modified22 February 2017
DownloadsMolfile
FormulaC12H16F3N
Net Charge0
Average Mass231.261
Monoisotopic Mass231.12348
SMILESCCN[C@@H](C)Cc1cccc(C(F)(F)F)c1
InChIInChI=1S/C12H16F3N/c1-3-16-9(2)7-10-5-4-6-11(8-10)12(13,14)15/h4-6,8-9,16H,3,7H2,1-2H3/t9-/m0/s1
InChIKeyDBGIVFWFUFKIQN-VIFPVBQESA-N
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
serotonin uptake inhibitor  A compound that specifically inhibits the reuptake of serotonin in the brain. This increases the serotonin concentration in the synaptic cleft which then activates serotonin receptors to a greater extent.
serotonergic agonist  An agent that has an affinity for serotonin receptors and is able to mimic the effects of serotonin by stimulating the physiologic activity at the cell receptors. Serotonin agonists are used as antidepressants, anxiolytics, and in the treatment of migraine disorders.
serotonin uptake inhibitor  A compound that specifically inhibits the reuptake of serotonin in the brain. This increases the serotonin concentration in the synaptic cleft which then activates serotonin receptors to a greater extent.
serotonergic agonist  An agent that has an affinity for serotonin receptors and is able to mimic the effects of serotonin by stimulating the physiologic activity at the cell receptors. Serotonin agonists are used as antidepressants, anxiolytics, and in the treatment of migraine disorders.
Applications:
appetite depressant  Any agent that is used to decrease appetite.
serotonin uptake inhibitor  A compound that specifically inhibits the reuptake of serotonin in the brain. This increases the serotonin concentration in the synaptic cleft which then activates serotonin receptors to a greater extent.
serotonergic agonist  An agent that has an affinity for serotonin receptors and is able to mimic the effects of serotonin by stimulating the physiologic activity at the cell receptors. Serotonin agonists are used as antidepressants, anxiolytics, and in the treatment of migraine disorders.
appetite depressant  Any agent that is used to decrease appetite.
serotonin uptake inhibitor  A compound that specifically inhibits the reuptake of serotonin in the brain. This increases the serotonin concentration in the synaptic cleft which then activates serotonin receptors to a greater extent.
serotonergic agonist  An agent that has an affinity for serotonin receptors and is able to mimic the effects of serotonin by stimulating the physiologic activity at the cell receptors. Serotonin agonists are used as antidepressants, anxiolytics, and in the treatment of migraine disorders.
ChEBI Ontology
Outgoing Relation(s)
(S)-fenfluramine (CHEBI:439329) has role appetite depressant (CHEBI:50507)
(S)-fenfluramine (CHEBI:439329) has role serotonergic agonist (CHEBI:35941)
(S)-fenfluramine (CHEBI:439329) has role serotonin uptake inhibitor (CHEBI:50949)
(S)-fenfluramine (CHEBI:439329) is a fenfluramine (CHEBI:5000)
(S)-fenfluramine (CHEBI:439329) is enantiomer of (R)-fenfluramine (CHEBI:521051)
Incoming Relation(s)
(S)-fenfluramine hydrochloride (CHEBI:59730) has part (S)-fenfluramine (CHEBI:439329)
(R)-fenfluramine (CHEBI:521051) is enantiomer of (S)-fenfluramine (CHEBI:439329)
IUPAC Name 
(2S)-N-ethyl-1-[3-(trifluoromethyl)phenyl]propan-2-amine
INNs  Source
dexfenfluraminaChemIDplus
dexfenfluramineChemIDplus
dexfenfluraminumChemIDplus
Synonyms  Source
dextrofenfluramineChEBI
d-N-ethyl-α-methyl-m-trifluoromethylphenethylamineChemIDplus
(+)-fenfluramineChemIDplus
(S)-N-ethyl-1-[3-(trifluoromethyl)phenyl]propan-2-amineChEBI
(S)-fenfluramineChemIDplus
Manual XrefsDatabases
832DrugCentral
D07805KEGG DRUG
DB01191DrugBank
LSM-5685LINCS
US3198834Patent
Registry NumbersSources
Beilstein:4783710Beilstein
CAS:3239-44-9ChemIDplus
Citations