(S)-fluoxetine (CHEBI:86992)

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ChEBI Name	(S)-fluoxetine

ChEBI ID	CHEBI:86992

ChEBI ASCII Name	(S)-fluoxetine

Definition	An N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine that has S configuration. [The antidepressant drug fluoxetine is a racemate comprising equimolar amounts of (R)- and (S)-fluoxetine].

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Formula

C17H18F3NO

Net Charge

Average Mass

309.32610

Monoisotopic Mass

309.13405

InChI

InChI=1S/C17H18F3NO/c1-21-12-11-16(13-5-3-2-4-6-13)22-15-9-7-14(8-10-15)17(18,19)20/h2-10,16,21H,11-12H2,1H3/t16-/m0/s1

InChIKey

RTHCYVBBDHJXIQ-INIZCTEOSA-N

SMILES

CNCC[C@H](Oc1ccc(cc1)C(F)(F)F)c1ccccc1

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	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.

Application(s):	antidepressant Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. 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.

ChEBI Ontology
Outgoing	(S)-fluoxetine (CHEBI:86992) has role antidepressant (CHEBI:35469) (S)-fluoxetine (CHEBI:86992) has role serotonin uptake inhibitor (CHEBI:50949) (S)-fluoxetine (CHEBI:86992) is a N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine (CHEBI:86990) (S)-fluoxetine (CHEBI:86992) is conjugate base of (S)-fluoxetine(1+) (CHEBI:86995) (S)-fluoxetine (CHEBI:86992) is enantiomer of (R)-fluoxetine (CHEBI:86991)

Incoming	fluoxetine (CHEBI:5118) has part (S)-fluoxetine (CHEBI:86992) (S)-fluoxetine(1+) (CHEBI:86995) is conjugate acid of (S)-fluoxetine (CHEBI:86992) (R)-fluoxetine (CHEBI:86991) is enantiomer of (S)-fluoxetine (CHEBI:86992)

IUPAC Name

(3S)-N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine

Synonyms	Sources
(−)-fluoxetine	ChEBI
(S)-(−)-fluoxetine	ChEBI
(S)-N-methyl-3-(4-trifluoromethylphenoxy)-3-phenylpropylamine	ChEBI
(S)-N-methyl-3-(4-trifluoromethylphenyloxy)-3-(phenyl)propylamine	ChEBI
(S)-N-methyl-3-phenyl-3-[(α,α,α-trifluoro-p-tolyl)oxy]propylamine	ChEBI
(S)-N-methyl-γ-(4-trifluoromethylphenoxy)-3-phenylpropylamine	ChEBI
(S)-Prozac	ChEBI

Registry Number	Type	Source
4356433	Reaxys Registry Number	Reaxys

Last Modified

20 July 2015