fluoxetine   Click here for help

GtoPdb Ligand ID: 203

Synonyms: Prozac®
Approved drug
fluoxetine is an approved drug (FDA (1987))
Compound class: Synthetic organic
Comment: The approved drug fluoxetine is a racemic mixture of two enantiomers; (R)-fluoxetine and (S)-Fluoxetine. The structure shown here does not specify stereochemistry and represents the mixture. The two PDB links listed above represent the two enantiomers. Fluoxetine is metabolised in the body to active metabolite norfluoxetine.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: fluoxetine

fluoxetine is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 21.26
Molecular weight 309.13
XLogP 4.65
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CNCCC(c1ccccc1)Oc1ccc(cc1)C(F)(F)F
Isomeric SMILES CNCCC(c1ccccc1)Oc1ccc(cc1)C(F)(F)F
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
InChI Key RTHCYVBBDHJXIQ-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Antidepressant of the selective serotonin uptake inhibitor class, used in the treatment of major depression and anxiety disorders. Additional indications include obsessive compulsive disorder (OCD), post-traumatic stress disorder (PTSD), bulimia nervosa, panic disorder, body dysmorphic disorder, premenstrual dysphoric disorder (PMDD) and trichotillomania (compulsive hair pulling).
fluoxetine, along with amiloride and riluzole are repurposing candidates as potential therapeutics for secondary progressive multiple sclerosis (SPMS or late MS), having already been shown to provide neuroprotective benefit [1,4,7-8]. A Phase 2 clinical trial (NCT01910259, MS-SMART trial) is recruiting patients (April 2015).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
SSRIs are potent inhibitors of neuronal serotonin reuptake. By blocking sertonin reuptake, they increase serotonin stimulation of somatodendritic and terminal 5-HT1A receptors, and enhance serotonergic neurotransmission.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT01910259 MS-SMART: Multiple Sclerosis-Secondary Progressive Multi-Arm Randomisation Trial Phase 2 Interventional University College, London