Page last updated: 2024-12-09

(R)-fluoxetine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

## (R)-Fluoxetine: The Enantiomer with a Research Spotlight

**What is (R)-fluoxetine?**

(R)-fluoxetine is one enantiomer of the widely-used antidepressant fluoxetine (Prozac). Enantiomers are molecules that are mirror images of each other, like your left and right hands. They have the same chemical formula but differ in their spatial arrangement.

**Why is (R)-fluoxetine important for research?**

It turns out that the two enantiomers of fluoxetine, (R)-fluoxetine and (S)-fluoxetine, have different pharmacological properties and effects in the body. While **(S)-fluoxetine is the primary active enantiomer responsible for the antidepressant effects of fluoxetine**, **(R)-fluoxetine is often considered inactive or minimally active.**

However, research has shown that **(R)-fluoxetine may still have some interesting effects:**

* **Potentiation of (S)-fluoxetine's effects:** Some studies suggest that (R)-fluoxetine can enhance the antidepressant activity of (S)-fluoxetine, possibly by inhibiting its metabolism. This has implications for developing more effective and efficient fluoxetine formulations.
* **Potential therapeutic role beyond antidepressant effects:** Research is exploring potential therapeutic applications of (R)-fluoxetine in areas like:
* **Neurodegenerative diseases:** (R)-fluoxetine may have neuroprotective properties, potentially beneficial in conditions like Alzheimer's disease.
* **Substance use disorders:** Preliminary evidence suggests (R)-fluoxetine could be helpful in treating addiction to alcohol, cocaine, and other substances.
* **Other mental health conditions:** Research is ongoing to investigate (R)-fluoxetine's potential role in treating anxiety, obsessive-compulsive disorder, and other mental health issues.
* **Understanding the mechanisms of action:** Studying (R)-fluoxetine helps researchers understand the specific mechanisms by which fluoxetine exerts its effects and identify which enantiomer contributes to which effects. This knowledge can lead to more targeted drug development and personalized treatment strategies.

**In conclusion, (R)-fluoxetine, although not the primary active component of fluoxetine, has garnered research interest due to its potential for: **

* **Enhancing the effectiveness of (S)-fluoxetine**
* **Possessing unique therapeutic properties beyond antidepressant effects**
* **Providing insights into the mechanisms of action of fluoxetine**

Further research is necessary to fully understand the therapeutic potential and safety of (R)-fluoxetine and its potential for treating various disorders.

(R)-fluoxetine : An N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine that has R configuration. [The antidepressant drug fluoxetine is a racemate comprising equimolar amounts of (R)- and (S)-fluoxetine]. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID1548970
CHEMBL ID153036
CHEBI ID86991
SCHEMBL ID1200433

Synonyms (39)

Synonym
BIDD:GT0614
methyl-[3-phenyl-3-(4-trifluoromethyl-phenoxy)-propyl]-amine
LOPAC0_000485
PDSP1_001304
PDSP2_001288
(+/-)-fluoxetine
NCGC00162170-01
(3r)-n-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine
RFX ,
bdbm50136166
methyl-[(r)-3-phenyl-3-(4-trifluoromethyl-phenoxy)-propyl]-amine
CHEMBL153036 ,
chebi:86991 ,
(r)-n-methyl-3-(4-trifluoromethylphenyloxy)-3-(phenyl)propylamine
(r)-n-methyl-gamma-(4-trifluoromethylphenoxy)-3-phenylpropylamine
(r)-fluoxetine
(r)-(+)-fluoxetine
(r)-n-methyl-3-phenyl-3-[(alpha,alpha,alpha-trifluoro-p-tolyl)oxy]propylamine
(r)-prozac
DB08472
(r)-n-methyl-3-(4-trifluoromethylphenoxy)-3-phenylpropylamine
(+)-fluoxetine
(3r)-n-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]-1-propanamine
A830402
CCG-204576
(r)-(+/-)-fluoxetine
fluoxetine, (r)-
100568-03-4
unii-f279341ruq
f279341ruq ,
benzenepropanamine, n-methyl-gamma-(4-(trifluoromethyl)phenoxy)-, (gammar)-
AKOS015914491
benzenepropanamine, n-methyl-.gamma.-(4-(trifluoromethyl)phenoxy)-, (.gamma.r)-
SCHEMBL1200433
DTXSID10872290
(r)-n-methyl-3-phenyl-3-(4-(trifluoromethyl)phenoxy)propan-1-amine
Q27097676
r-fluoxetine
benzenepropanamine,?n-methyl-.gamma.-[4-(trifluoromethyl)phenoxy]-, (.gamma.r)-
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
antidepressantAntidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
serotonin uptake inhibitorA 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.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amineAn aromatic ether consisting of 4-trifluoromethylphenol in which the hydrogen of the phenolic hydroxy group is replaced by a 3-(methylamino)-1-phenylpropyl group.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Sodium-dependent dopamine transporterRattus norvegicus (Norway rat)IC50 (µMol)1.00000.00070.97749.7000AID64685
Sodium-dependent serotonin transporterRattus norvegicus (Norway rat)Ki0.03080.00000.705610.0000AID204534
TransporterRattus norvegicus (Norway rat)IC50 (µMol)1.00000.00081.95628.8000AID147730
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (17)

Assay IDTitleYearJournalArticle
AID113260Antagonistic activity against acetic acid induced abdominal constriction (writhing) in mice, when administered in combination with 0.2 mg/kg of morphine1988Journal of medicinal chemistry, Jul, Volume: 31, Issue:7
Absolute configurations and pharmacological activities of the optical isomers of fluoxetine, a selective serotonin-uptake inhibitor.
AID587252Ratio of Ki for NET in rabbit cortical membrane to Ki for SERT in rabbit cortical membrane2011European journal of medicinal chemistry, Mar, Volume: 46, Issue:3
Synthesis, molecular docking and binding studies of selective serotonin transporter inhibitors.
AID147730Binding affinity against norepinephrine transporter (NET) by displacement of [3H]nisoxetine in male wistar rats2003Journal of medicinal chemistry, Dec-04, Volume: 46, Issue:25
Syntheses and binding studies of new [(aryl)(aryloxy)methyl]piperidine derivatives and related compounds as potential antidepressant drugs with high affinity for serotonin (5-HT) and norepinephrine (NE) transporters.
AID177554Ability to antagonize saccharin-induced drinking (palatability-induced ingestion) in rats1988Journal of medicinal chemistry, Jul, Volume: 31, Issue:7
Absolute configurations and pharmacological activities of the optical isomers of fluoxetine, a selective serotonin-uptake inhibitor.
AID587250Displacement of [3H]-Nisoxetine from NET in rabbit cortical membrane2011European journal of medicinal chemistry, Mar, Volume: 46, Issue:3
Synthesis, molecular docking and binding studies of selective serotonin transporter inhibitors.
AID204534Binding affinity to the serotonin transporter (SERT) measured by displacement of [3H]paroxetine in male wistar rats2003Journal of medicinal chemistry, Dec-04, Volume: 46, Issue:25
Syntheses and binding studies of new [(aryl)(aryloxy)methyl]piperidine derivatives and related compounds as potential antidepressant drugs with high affinity for serotonin (5-HT) and norepinephrine (NE) transporters.
AID116526Inhibition of serotonin uptake carrier in mice1988Journal of medicinal chemistry, Jul, Volume: 31, Issue:7
Absolute configurations and pharmacological activities of the optical isomers of fluoxetine, a selective serotonin-uptake inhibitor.
AID5476Binding affinity against 5-hydroxytryptamine 2A receptor by displacement of [3H]-ketanserin from rat prefrontal cerebral cortex mambranes2003Journal of medicinal chemistry, Dec-04, Volume: 46, Issue:25
Syntheses and binding studies of new [(aryl)(aryloxy)methyl]piperidine derivatives and related compounds as potential antidepressant drugs with high affinity for serotonin (5-HT) and norepinephrine (NE) transporters.
AID587251Displacement of [3H]-WIN 35,428 from DAT in rabbit striatal membrane2011European journal of medicinal chemistry, Mar, Volume: 46, Issue:3
Synthesis, molecular docking and binding studies of selective serotonin transporter inhibitors.
AID113259Antagonistic activity against acetic acid induced abdominal constriction (writhing) in mice1988Journal of medicinal chemistry, Jul, Volume: 31, Issue:7
Absolute configurations and pharmacological activities of the optical isomers of fluoxetine, a selective serotonin-uptake inhibitor.
AID3719Binding affinity against 5-hydroxytryptamine 1A receptor (5-HT1A) by displacement of [3H]8-OH-DPAT from rat hippocampus membranes2003Journal of medicinal chemistry, Dec-04, Volume: 46, Issue:25
Syntheses and binding studies of new [(aryl)(aryloxy)methyl]piperidine derivatives and related compounds as potential antidepressant drugs with high affinity for serotonin (5-HT) and norepinephrine (NE) transporters.
AID587253Ratio of Ki for DAT in rabbit striatal membrane to Ki for SERT in rabbit cortical membrane2011European journal of medicinal chemistry, Mar, Volume: 46, Issue:3
Synthesis, molecular docking and binding studies of selective serotonin transporter inhibitors.
AID110195Ability to antagonize p-chloroamphetamine-induced depletion of brain serotonin in mouse1988Journal of medicinal chemistry, Jul, Volume: 31, Issue:7
Absolute configurations and pharmacological activities of the optical isomers of fluoxetine, a selective serotonin-uptake inhibitor.
AID499952Displacement of [3H]leucine from Leucine transporter2010Journal of medicinal chemistry, Aug-26, Volume: 53, Issue:16
Structure-activity relationships for a novel series of citalopram (1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile) analogues at monoamine transporters.
AID64685Binding affinity against dopamine transporter (DAT) by displacement of [3H]WIN-35428 in male wistar rats2003Journal of medicinal chemistry, Dec-04, Volume: 46, Issue:25
Syntheses and binding studies of new [(aryl)(aryloxy)methyl]piperidine derivatives and related compounds as potential antidepressant drugs with high affinity for serotonin (5-HT) and norepinephrine (NE) transporters.
AID587249Displacement of [3H]-paroxetine from SERT in rabbit cortical membrane2011European journal of medicinal chemistry, Mar, Volume: 46, Issue:3
Synthesis, molecular docking and binding studies of selective serotonin transporter inhibitors.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (20.00)18.7374
1990's0 (0.00)18.2507
2000's1 (20.00)29.6817
2010's3 (60.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 25.86

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index25.86 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.32 (4.65)
Search Engine Demand Index26.67 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (25.86)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]