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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H18F3NO
Molecular Weight 309.3261
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUOXETINE, (S)-

SMILES

CNCC[C@H](OC1=CC=C(C=C1)C(F)(F)F)C2=CC=CC=C2

InChI

InChIKey=RTHCYVBBDHJXIQ-INIZCTEOSA-N
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

HIDE SMILES / InChI

Molecular Formula C17H18F3NO
Molecular Weight 309.3261
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

S-fluoxetine is an enantiomer of fluoxetine, a potent and selective inhibitor of the neuronal serotonin-uptake carrier and a clinically effective antidepressant. R-fluoxetine and S-fluoxetine enantiomers are nearly equipotent at blocking serotonin reuptake. In all biochemical and pharmacological studies, the eudismic ratio for the fluoxetine enantiomers is also near unity. A study examining the relative contributions of CYP enzymes to the metabolism of S-fluoxetine, and R-fluoxetine found dramatic differences. These data led to discovery programs between Lilly and Sepracor for the individual enantiomers. S-fluoxetine was studied in a phase 2 clinical trial for the prophylaxis of migraine, however, development was discontinued.

Approval Year

Targets

Targets

Conditions
Doses

Doses

DosePopulationAdverse events​
40 mg 1 times / day multiple, oral (total daily dose)
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy
n = 27
Health Status: unhealthy
Condition: migraine
Sex: M+F
Food Status: UNKNOWN
Population Size: 27
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Absolute configurations and pharmacological activities of the optical isomers of fluoxetine, a selective serotonin-uptake inhibitor.
1988 Jul
Interaction of the enantiomers of fluoxetine and norfluoxetine with human liver cytochromes P450.
1993 Aug
(R)-, (S)-, and racemic fluoxetine N-demethylation by human cytochrome P450 enzymes.
2000 Oct
Patents

Sample Use Guides

The amount of S( )fluoxetine or pharmaceutically acceptable salt thereof is administered at a rate of 1mg to 100mg, preferably 20mg to 80mg and most preferably 25mg to 75mg per day.
Route of Administration: Oral
P. promelas feeding rate, an ecologically relevant and mode-of-action related response, was the most sensitive endpoint tested for R- and S-fluoxetine with 10% effect concentration (EC10) values (+/-SE) of 16.1 (+/-20.2) and 3.7 (+/-4.6) microg l(-1), respectively. Up to a 9.4-fold difference in toxicity between enantiomers was observed; P. promelas growth EC10s (+/-SE) for R- and S-fluoxetine were 132.9 (+/-21.2) and 14.1 (+/-8.1) microg l(-1), respectively.
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:37:26 GMT 2023
Edited
by admin
on Sat Dec 16 09:37:26 GMT 2023
Record UNII
6MYD4C025Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FLUOXETINE, (S)-
Common Name English
FLUOXETINE, (-)-
Common Name English
(S)-N-METHYL-3-(4-TRIFLUOROMETHYLPHENOXY)-3-PHENYLPROPYLAMINE
Systematic Name English
BENZENEPROPANAMINE, N-METHYL-.GAMMA.-(4-(TRIFLUOROMETHYL)PHENOXY)-, (.GAMMA.S)-
Systematic Name English
(-)-FLUOXETINE
Common Name English
Code System Code Type Description
CHEBI
86992
Created by admin on Sat Dec 16 09:37:27 GMT 2023 , Edited by admin on Sat Dec 16 09:37:27 GMT 2023
PRIMARY
EPA CompTox
DTXSID60904656
Created by admin on Sat Dec 16 09:37:27 GMT 2023 , Edited by admin on Sat Dec 16 09:37:27 GMT 2023
PRIMARY
DRUG BANK
DB08544
Created by admin on Sat Dec 16 09:37:27 GMT 2023 , Edited by admin on Sat Dec 16 09:37:27 GMT 2023
PRIMARY
CAS
100568-02-3
Created by admin on Sat Dec 16 09:37:27 GMT 2023 , Edited by admin on Sat Dec 16 09:37:27 GMT 2023
PRIMARY
PUBCHEM
1548968
Created by admin on Sat Dec 16 09:37:27 GMT 2023 , Edited by admin on Sat Dec 16 09:37:27 GMT 2023
PRIMARY
FDA UNII
6MYD4C025Q
Created by admin on Sat Dec 16 09:37:27 GMT 2023 , Edited by admin on Sat Dec 16 09:37:27 GMT 2023
PRIMARY
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