114247-06-2

Usage

Uses

Used in Pharmaceutical Industry:
S-(+)-FLUOXETINE HYDROCHLORIDE is used as an antidepressant for treating various forms of depression and related disorders. It works by selectively inhibiting the reuptake of serotonin in the brain, thereby increasing the availability of serotonin and helping to alleviate symptoms of depression.
Used in Mental Health Treatment:
S-(+)-FLUOXETINE HYDROCHLORIDE is used as a psychotropic agent for managing mental health conditions such as obsessive-compulsive disorder (OCD), bulimia nervosa, and panic disorder. Its ability to modulate serotonin levels in the brain makes it an effective treatment option for these conditions.
Used in Veterinary Medicine:
S-(+)-FLUOXETINE HYDROCHLORIDE is also used as a veterinary drug for treating behavioral and mood disorders in animals, such as separation anxiety and obsessive-compulsive behaviors in dogs and cats. Its application in veterinary medicine helps improve the quality of life for pets suffering from these conditions.

Biochem/physiol Actions

Fluoxetine hcl (hydrochloride) is a selective serotonin reuptake inhibitor and functions as an antidepressant. This drug works at presynaptic terminals where it prevents the reuptake of serotonin, resulting in the accumulation of serotonin in extracellular fluid at synapses.

InChI:InChI=1/C17H18F3NO.ClH/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;1H/t16-;/m0./s1

Upstream product

• 98-56-6 4-chlorobenzotrifluoride 
• 74-89-5 methylamine 
• 51699-49-1 3-hydroxy-3-phenylpropyl 4-methylbenzenesulfonate 
• 73627-97-1 3-hydroxy-3-phenylpropanenitrile 
• 191729-88-1 (S)-3-Phenyl-3-(4-trifluoromethyl-phenoxy)-propionitrile 
• 191729-85-8 (R)-2-Phenyl-2-(4-trifluoromethyl-phenoxy)-ethanol 
• 126924-38-7 (S)-norfluoxetine 
• 402-45-9 4-hydroxybenzotrifluoride 
• 406945-09-3 (S)-N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propanamide 
• 406945-07-1 (S)-2-(3-furyl)-1-phenylethyl[1-(trifluoromethyl)phenyl] ether 
• 406945-08-2 (S)-3-phenyl-3-(4-(trifluoromethyl)phenoxy)propionic acid 
• 184844-76-6 (S)-2-(3-furyl)-1-phenyl-1-ethanol 
• 100-52-7 benzaldehyde 
• 130194-42-2 (1S)-3-amino-1-phenyl-1-propanol 

Relevant academic research and scientific papers

Preparation of polymer-supported Ru-TsDPEN catalysts and use for enantioselective synthesis of (S)-fluoxetine

Polymer-supported chiral ligands 9 and 17 were prepared based on Noyori's (1S,2S)- or (1R,2R)-N-(p-tolylsulfonyl)-1,2-diphenylethylenediamine. The combination with [RuCl2(p-cymene)]2 has been shown to exhibit high activities and enantioselectivities for heterogeneous asymmetric transfer hydrogenation of aromatic ketones (19a-c) with formic acid-triethylamine azeotrope as the hydrogen donor, whereby affording the respective optically active alcohols 20a-c, the key precursors of chiral fluoxetine. As exemplified by ligand 17 for substrate 19c, the catalysts can be recovered and reused in three consecutive runs with no significant decline in enantioselectivity. The procedure avoids the plausible contamination of fluoxetine by the toxic transition metal species. The Royal Society of Chemistry 2005.

Pure S(+)isomer fluoxetine

Methods and compositions are disclosed utilizing the pure S(+) isomer of fluoxetine which is a potent antidepressant and appetite suppressant substantially free of unwanted, adverse toxic or psychological effects, for the treatment of human depression. In addition, methods and compositions are disclosed utilizing the pure S(+) isomer of fluoxetine which is useful in treating migraine headaches, pain, in particular chronic pain, and obsessive-compulsive disorders. Further, methods and compositions for treating a condition alleviated or improved by inhibition of serotonin uptake in serotonergic neurons and platelets in a human using optically pure S(+) fluoxetine are disclosed.

Pd-catalyzed kinetic resolution of benzylic alcohols: A practical synthesis of (R)-tomoxetine and (S)-fluoxetine hydrochlorides

A convenient synthetic route to (R)-tomoxetine hydrochloride (90% ee) and (S)-fluoxetine hydrochloride (84% ee) is described. (S)-3-Phenyl-3-hydroxypropyl p-toluenesulphonate, the key intermediate, is obtained by the oxidative kinetic resolution of the corresponding racemic 3-phenyl-3-hydroxypropyl p-toluenesulphonate using (-)-sparteine/Pd(II)/O2 (1 atm) catalytic system.

Enantioselective synthesis of (S)- and (R)-fluoxetine hydrochloride

The enantioselective synthesis of fluoxetine hydrochloride, a potent serotonin-uptake inhibitor, is described. The synthesis of (S)-fluoxetine hydrochloride begins with the asymmetric carbonyl-ene reaction of benzaldehyde with 3-methylene-2,3-dihydrofuran (1) catalyzed by Ti[OCH(CH3)2]4/(S)-BINOL to give (S)-2-(3-furyl)-1-phenyl-1-ethanol (2) in 90% yield and 95% ee. In five steps, alcohol 2 was converted into (S)-fluoxetine hydrochloride (97% ee and 56% overall yield from benzaldehyde). (R)-fluoxetine hydrochloride was prepared by the same sequence except that Ti[OCH(CH3)2]4/(R)-BINOL was used in the first reaction to give the enantiomer of 2.

Methods for treating depression and other disorders using optically pure R (-) fluoxetine and monoamine oxidase inhibitor

A method and composition are utilizing the pure R(-) isomer of fluoxetine which is a potent antidepressant and appetite suppressant substantially free of adverse effects. In addition, a method and composition are disclosed utilizing the pure R(-) isomer of fluoxetine which is useful to treat migraine headaches, pain, in particular chronic pain, psychoactive substance abuse disorders and obsessive compulsive disorders.

A convenient method for preparing enantiomerically pure norfluoxetine, fluoxetine and tomoxetine

A convenient synthesis for enantiomers of norfluoxetine, fluoxetine and tomoxetine is described. All final products were derived from a common intermediate, 3-phenyl-3-hydroxypropylamine.

Hydrolases in organic synthesis: Preparation of enantiomerically pure compounds

Esterhydrolases (Esterases, Lipases) are highly (chemo-, regio- and enantio-) selective biocatalysts for the transformation of racemic and achiral substrates into enantiomerically pure compounds.Numerous examples for their application in the preparation of synthetically useful chiral auxiliaries and building blocks for flavour compounds, pheromones and several pharmaceuticals including β-adrenergic blockers, antidepressants and ACE inhibitors are presented.

Asymmetric Synthesis of Both Enantiomers of Fluoxetine via Microbiological Reduction of Ethyl Benzoylacetate

Microbiological reduction of ethyl benzoylacetate by bakers' yeast (Saccharomyces cerevisiae), Beauveria sulfurescens or Geotrichum candidum afforded ethyl (S)-3-hydroxy-3-phenylpropionate in high optical yield.This enantiomerically pure alcohol was converted into both enantiomers of fluoxetine (7).The product resulting from the bakers' yeast reduction had ee values (87-93percent) lower than the 100percent value erroneously attributed in earlier studies.Key Words: Fluoxetine; asymmetric synthesis; bioreduction; bakers' yeast; Beauveria sulfurescens; Geotrichum candidum.