## (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]
ID Source | ID |
---|---|
PubMed CID | 1548970 |
CHEMBL ID | 153036 |
CHEBI ID | 86991 |
SCHEMBL ID | 1200433 |
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)- |
Role | Description |
---|---|
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. |
[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] |
Class | Description |
---|---|
N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine | An 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 | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
Sodium-dependent dopamine transporter | Rattus norvegicus (Norway rat) | IC50 (µMol) | 1.0000 | 0.0007 | 0.9774 | 9.7000 | AID64685 |
Sodium-dependent serotonin transporter | Rattus norvegicus (Norway rat) | Ki | 0.0308 | 0.0000 | 0.7056 | 10.0000 | AID204534 |
Transporter | Rattus norvegicus (Norway rat) | IC50 (µMol) | 1.0000 | 0.0008 | 1.9562 | 8.8000 | AID147730 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID113260 | Antagonistic activity against acetic acid induced abdominal constriction (writhing) in mice, when administered in combination with 0.2 mg/kg of morphine | 1988 | Journal of medicinal chemistry, Jul, Volume: 31, Issue:7 | Absolute configurations and pharmacological activities of the optical isomers of fluoxetine, a selective serotonin-uptake inhibitor. |
AID587252 | Ratio of Ki for NET in rabbit cortical membrane to Ki for SERT in rabbit cortical membrane | 2011 | European journal of medicinal chemistry, Mar, Volume: 46, Issue:3 | Synthesis, molecular docking and binding studies of selective serotonin transporter inhibitors. |
AID147730 | Binding affinity against norepinephrine transporter (NET) by displacement of [3H]nisoxetine in male wistar rats | 2003 | Journal 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. |
AID177554 | Ability to antagonize saccharin-induced drinking (palatability-induced ingestion) in rats | 1988 | Journal of medicinal chemistry, Jul, Volume: 31, Issue:7 | Absolute configurations and pharmacological activities of the optical isomers of fluoxetine, a selective serotonin-uptake inhibitor. |
AID587250 | Displacement of [3H]-Nisoxetine from NET in rabbit cortical membrane | 2011 | European journal of medicinal chemistry, Mar, Volume: 46, Issue:3 | Synthesis, molecular docking and binding studies of selective serotonin transporter inhibitors. |
AID204534 | Binding affinity to the serotonin transporter (SERT) measured by displacement of [3H]paroxetine in male wistar rats | 2003 | Journal 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. |
AID116526 | Inhibition of serotonin uptake carrier in mice | 1988 | Journal of medicinal chemistry, Jul, Volume: 31, Issue:7 | Absolute configurations and pharmacological activities of the optical isomers of fluoxetine, a selective serotonin-uptake inhibitor. |
AID5476 | Binding affinity against 5-hydroxytryptamine 2A receptor by displacement of [3H]-ketanserin from rat prefrontal cerebral cortex mambranes | 2003 | Journal 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. |
AID587251 | Displacement of [3H]-WIN 35,428 from DAT in rabbit striatal membrane | 2011 | European journal of medicinal chemistry, Mar, Volume: 46, Issue:3 | Synthesis, molecular docking and binding studies of selective serotonin transporter inhibitors. |
AID113259 | Antagonistic activity against acetic acid induced abdominal constriction (writhing) in mice | 1988 | Journal of medicinal chemistry, Jul, Volume: 31, Issue:7 | Absolute configurations and pharmacological activities of the optical isomers of fluoxetine, a selective serotonin-uptake inhibitor. |
AID3719 | Binding affinity against 5-hydroxytryptamine 1A receptor (5-HT1A) by displacement of [3H]8-OH-DPAT from rat hippocampus membranes | 2003 | Journal 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. |
AID587253 | Ratio of Ki for DAT in rabbit striatal membrane to Ki for SERT in rabbit cortical membrane | 2011 | European journal of medicinal chemistry, Mar, Volume: 46, Issue:3 | Synthesis, molecular docking and binding studies of selective serotonin transporter inhibitors. |
AID110195 | Ability to antagonize p-chloroamphetamine-induced depletion of brain serotonin in mouse | 1988 | Journal of medicinal chemistry, Jul, Volume: 31, Issue:7 | Absolute configurations and pharmacological activities of the optical isomers of fluoxetine, a selective serotonin-uptake inhibitor. |
AID499952 | Displacement of [3H]leucine from Leucine transporter | 2010 | Journal 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. |
AID64685 | Binding affinity against dopamine transporter (DAT) by displacement of [3H]WIN-35428 in male wistar rats | 2003 | Journal 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. |
AID587249 | Displacement of [3H]-paroxetine from SERT in rabbit cortical membrane | 2011 | European journal of medicinal chemistry, Mar, Volume: 46, Issue:3 | Synthesis, molecular docking and binding studies of selective serotonin transporter inhibitors. |
AID1159607 | Screen for inhibitors of RMI FANCM (MM2) intereaction | 2016 | Journal 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] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 1 (20.00) | 18.7374 |
1990's | 0 (0.00) | 18.2507 |
2000's | 1 (20.00) | 29.6817 |
2010's | 3 (60.00) | 24.3611 |
2020's | 0 (0.00) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
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.
| This Compound (25.86) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 0 (0.00%) | 5.53% |
Reviews | 0 (0.00%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 5 (100.00%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |