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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2D Structure
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Physico-chemical Properties
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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
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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
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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