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
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
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL228 |
6.1 nM [Ki] | ||
Target ID: CHEMBL289 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8355218/ |
0.22 µM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | Unknown Approved UseUnknown |
Doses
Dose | Population | Adverse 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: |
PubMed
Title | Date | PubMed |
---|---|---|
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17582462
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
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admin
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Edited
Sat Dec 16 09:37:26 GMT 2023
by
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Sat Dec 16 09:37:26 GMT 2023
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Record UNII |
6MYD4C025Q
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Record Status |
Validated (UNII)
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Record Version |
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