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Cas Database




  • Product Name:(S)-fluoxetine

  • CAS Number: 100568-02-3


  • Molecular Weight:309.331

  • Molecular Formula: C17H18F3NO

  • HS Code:

  • Mol File:100568-02-3.mol


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Relevant articles and documentsAll total 68 Articles be found

Synthesis, anorexigenic activity and QSAR of substituted aryloxypropanolamines

Srivastava, Shipra,Bhandari, Kalpana,Shankar, Girija,Singh,Saxena, Anil K.

, p. 631 - 642 (2004)

Substituted aryloxypropanolamines (6-20) were synthesized and evaluated for their anorexigenic activity. Among them 4-cyanoaryloxy (7), 2-methylaryloxy (9), 2-methoxyl aryloxy (10), 4-acetamidoaryloxy (15), 4-bromoaryloxy (16) and 4-ethylaminoaryloxy (20) exhibited potent anorexigenic activity. According to QSAR studies, the electronic parameter 'σ' plays an important role in describing the variance in activity. Birkhaeuser Boston 2004.

An asymmetric dihydroxylation route to enantiomerically pure norfluoxetine and fluoxetine

Pandey, Rajesh Kumar,Fernandes, Rodney A.,Kumar, Pradeep

, p. 4425 - 4426 (2002)

An efficient, practical asymmetric synthesis of (R)-norfluoxetine 1 and (R)-fluoxetine 2 has been achieved. The synthetic strategy features a Sharpless asymmetric dihydroxylation (SAD) route to the common building block 1,3-amino alcohol 9, from which (R)-norfluoxetine, (R)-fluoxetine and other related analogs can be synthesized.

Chemoenzymatic Synthesis of Both Enantiomers of Fluoxetine

Chenevert, Robert,Fortier, Genevieve

, p. 1603 - 1606 (1991)

Both enantiomers of fluoxetine have been synthesized from ethyl benzoylacetate.The key step is the enantioselective reduction of the starting material by baker's yeast.

Synthesis of R- and S- fluoxetine, norfluoxetine and related compounds from styrene oxide


, p. 1231 - 1238 (1995)

A facile, high yield synthesis of R-- or S--fluoxetine and norfluoxetine is described. This synthetic route utilizes readily available starting materials.

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

Chenevert, Robert,Fortier, Genevieve,Rhlid, Rachid Bel

, p. 6769 - 6776 (1992)

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.

Asymmetric dihydroxylation route to (R)-isoprenaline, (R)-norfluoxetine and (R)-fluoxetine

Kumar, Pradeep,Upadhyay, Rajesh Kumar,Pandey, Rajesh Kumar

, p. 3955 - 3959 (2004)

An efficient asymmetric synthesis of enantiomerically pure (R)-isoprenaline, (R)-norfluoxetine and (R)-fluoxetine is described using Sharpless asymmetric dihydroxylation as the key step.

Enantioselective hydrogenation of β-ketoesters using a MeO-PEG-supported Biphep ligand under atmospheric pressure: A practical synthesis of (S)-fluoxetine

Chai, Liting,Chen, Huansheng,Li, Zhiming,Wang, Quanrui,Tao, Fenggang

, p. 2395 - 2398 (2006)

The preparation of a novel chiral 2,2′-bis(MeO-PEG-supported)-6, 6′-bis(diphenylphosphanyl)biphenyl (MeO-PEG-Biphep) ligand is described. The derived ruthenium complex catalyzes the hydrogenation of β-ketoesters in up to 99% yield and 99% ee under atmospheric pressure. The accelerating effects exerted by the PEG linkage are dramatic when compared to the unsupported analogue, MeO-Biphep-RuBr2. Furthermore, the catalyst can be recovered easily and the recycled catalysts were shown to maintain their efficiency in two consecutive runs, albeit with declining activity. One of the products, (S)-ethyl-3-hydroxy-3-phenylpropanoate, is useful in the preparation of (S)-fluoxetine. Georg Thieme Verlag Stuttgart.

Influence of gasoline inhalation on the enantioselective pharmacokinetics of fluoxetine in rats

Cardoso, Juciane Lauren Cavalcanti,Lanchote, Vera Lucia,Pereira, Maria Paula Marques,Capela, Jorge Manuel Vieira,Lepera, José Salvador

, p. 206 - 210 (2013)

Fluoxetine is used clinically as a racemic mixture of (+)-(S) and (-)-(R) enantiomers for the treatment of depression. CYP2D6 catalyzes the metabolism of both fluoxetine enantiomers. We aimed to evaluate whether exposure to gasoline results in CYP2D inhibition. Male Wistar rats exposed to filtered air (n = 36; control group) or to 600 ppm of gasoline (n = 36) in a nose-only inhalation exposure chamber for 6 weeks (6 h/day, 5 days/week) received a single oral 10-mg/kg dose of racemic fluoxetine. Fluoxetine enantiomers in plasma samples were analyzed by a validated analytical method using LC-MS/MS. The separation of fluoxetine enantiomers was performed in a Chirobiotic V column using as the mobile phase a mixture of ethanol:ammonium acetate 15 mM. Higher plasma concentrations of the (+)-(S)-fluoxetine enantiomer were found in the control group (enantiomeric ratio AUC(+)-(S)/(-)-(R) = 1.68). In animals exposed to gasoline, we observed an increase in AUC0-??? for both enantiomers, with a sharper increase seen for the (-)-(R)-fluoxetine enantiomer (enantiomeric ratio AUC(+)-(S)/(-)-(R) = 1.07), resulting in a loss of enantioselectivity. Exposure to gasoline was found to result in the loss of enantioselectivity of fluoxetine, with the predominant reduction occurring in the clearance of the (-)-(R)-fluoxetine enantiomer (55% vs. 30%). Chirality 25:206-210, 2013. 2013 Wiley Periodicals, Inc. Copyright

Fe(OTf)3-catalyzed tandem Meyer-Schuster rearrangement/intermolecular hydroamination of 3-aryl propargyl alcohols for the synthesis of acyclic β-Aminoketones

Tao, Ruiheng,Yin, Yan,Duan, Yongbin,Sun, Yuxing,Sun, Yue,Cheng, Fengkai,Pan, Jinpeng,Lu, Cheng,Wang, Yuan

, p. 1762 - 1768 (2017)

Fe(OTf)3-catalyzed synthesis of acyclic β-aminoketones from 3-aryl propargyl alcohols and nitrogen nucleophiles were investigated. Results showed that propargyl alcohols without bulky groups α to the hydroxyl group underwent the transformation smoothly. Sulphonamides exhibited the higher reactivity than amides as the nitrogen nucleophiles and the transformation of acyclic β-aminoketones were finished in shorter reaction time and higher yields. Finally, racemic fluoxetine was efficiently accessed with the present reaction as the first step. This novel synthesis of acyclic β-aminoketones probable proceeded a Fe(OTf)3-catalyzed Meyer-Schuster rearrangement of 3-aryl propargyl alcohols, followed by a intermolecular hydroamination between nitrogen nucleophiles and α, β-unsaturated ketones.

Absolute configurations and pharmacological activities of the optical isomers of fluoxetine, a selective serotonin-uptake inhibitor


, p. 1412 - 1417 (1988)

Fluoxetine is a potent and selective inhibitor of the neuronal serotonin-uptake carrier and is a clinically effective antidepressant. Although fluoxetine is used therapeutically as the racemate, there appears to be a small but demonstrable stereospecificity associated with its interactions with the serotonin-uptake carrier. The goals of this study were to determine the absolute configurations of the enantiomers of fluoxetine and to examine whether the actions of fluoxetine in behavioral tests were enantiospecific. (S)-Fluoxetine was synthesized from (S)-(-)-3-chloro-1-phenylpropanol by sequential reaction with sodium iodide, methylamine, sodium hybride, and 4-fluoro-benzotrifluoride. (S)-Fluoxetine is dextrorotatory (+ 1.60) in methanol, but is levorotatory (- 10.85) in water. Fluoxetine enantiomers were derivatized with (R)-1-(1-naphthyl)ethyl isocyanate, and the resulting ureas were assaysed by 1H NMR or HPLC to determine optical purities of the fluoxetine samples. Both enantiomers antagonized writhing in mice; following sc administration of (R)- and (S)-fluoxetine, ED50 values were 15.3 and 25.7 mg/kg, respectively. Moreover, both enantiomers potentiated a subthreshold analgesic dose (0.25 mg/kg) of morphine, and ED50 values were 3.6 and 5.7 mg/kg, respectively. Following ip administration to mice, the two stereoisomers antagonized p-chloroamphetamine-induced depletion of whole brain serotonin concentrations. ED50 values for (S)- and (R)- fluoxetine were 1.2 and 2.1 mg/kg, respectively. The two enantiomers decreased palatability-induced ingestion following ip administration to rats; (R)- and (S)-fluoxetine reduced saccharin-induced drinking with ED50 values of 6.1 and 4.9 mg/kg, respectively. Thus, in all biochemical and pharmacological studies to date, the eudismic ratio for the fluoxetine enantiomers is near unity.

Sequential metabolism of secondary alkyl amines to metabolic-intermediate complexes: Opposing roles for the secondary hydroxylamine and primary amine metabolites of desipramine, (S)-fluoxetine, and N-desmethyldiltiazem

Hanson, Kelsey L.,VandenBrink, Brooke M.,Babu, Kantipudi N.,Allen, Kyle E.,Nelson, Wendel L.,Kunze, Kent L.

, p. 963 - 972 (2010)

Three secondary amines desipramine (DES), (S)-fluoxetine [(S)-FLX], and N-desmethyldiltiazem (MA) undergo N-hydroxylation to the corresponding secondary hydroxylamines [N-hydroxydesipramine, (S)-N-hydroxyfluoxetine, and N-hydroxy-N-desmethyldiltiazem] by cytochromes P450 2C11, 2C19, and 3A4, respectively. The expected primary amine products, N-desmethyldesipramine, (S)-norfluoxetine, and N,N-didesmethyldiltiazem, are also observed. The formation of metabolic-intermediate (MI) complexes from these substrates and metabolites was examined. In each example, the initial rates of MI complex accumulation followed the order secondary hydroxylamine > secondary amine ? primary amine, suggesting that the primary amine metabolites do not contribute to formation of MI complexes from these secondary amines. Furthermore, the primary amine metabolites, which accumulate in incubations of the secondary amines, inhibit MI complex formation. Mass balance studies provided estimates of the product ratios of N-dealkylation to N-hydroxylation. The ratios were 2.9 (DES-CYP2C11), 3.6 [(S)-FLX-CYP2C19], and 0.8 (MA-CYP3A4), indicating that secondary hydroxylamines are significant metabolites of the P450-mediated metabolism of secondary alkyl amines. Parallel studies with N-methyl-d3-desipramine and CYP2C11 demonstrated significant isotopically sensitive switching from N-demethylation to N-hydroxylation. These findings demonstrate that the major pathway to MI complex formation from these secondary amines arises from N-hydroxylation rather than N-dealkylation and that the primary amines are significant competitive inhibitors of MI complex formation. Copyright

Maltooligosaccharides as chiral selectors for the separation of pharmaceuticals by capillary electrophoresis

Soini, Helena,Stefansson, Morgan,Rlekkola, Marja-Lllsa,Novotny, Mllos V.

, p. 3477 - 3484 (1994)

Complexation between the linear maltodextrin oligosaccharides and certain enantiomeric compounds of pharmaceutical interest in buffered solutions can lead to an analytically desirable chiral recognition. Different maltodextrins were assessed in their capacity to cause enantiomeric separations under various conditions of capillary electrophoresis. The mechanism of chiral recognition has been probed through electrophoretic mobility and selectivity measurements for different buffer solutions and organic solvent additives. A differential interaction of chiral solutes with the maltodextrin helical entities emerges as the basis of such enantioselectivity. This notion is further supported by 1H- and 13C-NMR experiments. Optimized separations of simendan, ibuprofen, warfarin, and ketoprofen enantiomers are demonstrated together with a chiral determination of ibuprofen in a blood serum sample at the therapeutic level.

Simultaneous enantioselective determination of seven psychoactive drugs enantiomers in multi-specie animal tissues with chiral liquid chromatography coupled with tandem mass spectrometry

Zhu,Li, Shuang,Zhou, Li,Li, Qing,Guo, Xingjie

, (2019)

In stock farming, illegal use of antipsychotics has caused the food safety problem. This paper presents for the first time, a multi-residues method for the simultaneous enantioselective determination of seven antipsychotics in pork, beef and lamb muscles. The behaviors of Chiralpak AGP toward changes in pH and organic modifier in mobile phase were studied, and all analytes were rapidly separated within 30 min. The calibration curves of all enantiomers were linear in the range of 1–250 ng g?1, with correlation coefficient above 0.9931. The recoveries of the targeted compounds were higher than 82.1%, with repeatability and intermediate precision lower than 18.2% and 17.4%, respectively. In three matrices, the limit of detection and limit of quantification ranged from 0.20 to 0.65 ng g?1 and from 0.40 to 1.00 ng g?1, respectively. The proposed method can be used to provide additional information for the reliable risk assessment of chiral antipsychotics.

Truly-Biocompatible Gold Catalysis Enables Vivo-Orthogonal Intra-CNS Release of Anxiolytics

Adam, Catherine,Becker, Catherina G.,Hamilton, Lloyd,Ortega-Liebana, M. Carmen,Porter, Nicola J.,Sieger, Dirk,Unciti-Broceta, Asier,Valero, Teresa

supporting information, (2021/11/22)

Being recognized as the best-tolerated of all metals, the catalytic potential of gold (Au) has thus far been hindered by the ubiquitous presence of thiols in organisms. Herein we report the development of a truly-catalytic Au-polymer composite by assembling ultrasmall Au-nanoparticles at the protein-repelling outer layer of a co-polymer scaffold via electrostatic loading. Illustrating the in vivo-compatibility of the novel catalysts, we show their capacity to uncage the anxiolytic agent fluoxetine at the central nervous system (CNS) of developing zebrafish, influencing their swim pattern. This bioorthogonal strategy has enabled -for the first time- modification of cognitive activity by releasing a neuroactive agent directly in the brain of an animal.

Tuning the activity of known drugs via the introduction of halogen atoms, a case study of SERT ligands – Fluoxetine and fluvoxamine

Bojarski, Andrzej J.,Bugno, Ryszard,Duszyńska, Beata,Hogendorf, Adam S.,Hogendorf, Agata,Kurczab, Rafa?,Lenda, Tomasz,Pietru?, Wojciech,Sata?a, Grzegorz,Staroń, Jakub,Wantuch, Anna,Warszycki, Dawid

, (2021/06/02)

The selective serotonin reuptake inhibitors (SSRIs), acting at the serotonin transporter (SERT), are one of the most widely prescribed antidepressant medications. All five approved SSRIs possess either fluorine or chlorine atoms, and there is a limited number of reports describing their analogs with heavier halogens, i.e., bromine and iodine. To elucidate the role of halogen atoms in the binding of SSRIs to SERT, we designed a series of 22 fluoxetine and fluvoxamine analogs substituted with fluorine, chlorine, bromine, and iodine atoms, differently arranged on the phenyl ring. The obtained biological activity data, supported by a thorough in silico binding mode analysis, allowed the identification of two partners for halogen bond interactions: the backbone carbonyl oxygen atoms of E493 and T497. Additionally, compounds with heavier halogen atoms were found to bind with the SERT via a distinctly different binding mode, a result not presented elsewhere. The subsequent analysis of the prepared XSAR sets showed that E493 and T497 participated in the largest number of formed halogen bonds. The XSAR library analysis led to the synthesis of two of the most active compounds (3,4-diCl-fluoxetine 42, SERT Ki = 5 nM and 3,4-diCl-fluvoxamine 46, SERT Ki = 9 nM, fluoxetine SERT Ki = 31 nM, fluvoxamine SERT Ki = 458 nM). We present an example of the successful use of a rational methodology to analyze binding and design more active compounds by halogen atom introduction. ‘XSAR library analysis’, a new tool in medicinal chemistry, was instrumental in identifying optimal halogen atom substitution.

Method for synthesizing chiral secondary alcohol compound


Paragraph 0160-0166, (2021/05/29)

The invention discloses a method for synthesizing a chiral secondary alcohol compound. The method comprises the following step of: reacting a ketone compound in an aprotic organic solvent at room temperature and inert gas atmosphere under the action of a chiral cobalt catalyst and an activating agent by taking a combination of bis(pinacolato)diboron and alcohol or water as a reducing agent to obtain the chiral secondary alcohol compound. According to the method disclosed by the invention, a combination of pinacol diborate and alcohol or water which are cheap, stable and easy to obtain is taken as a reducing agent, and a ketone compound is efficiently reduced to synthesize a corresponding chiral secondary alcohol compound in an aprotic organic solvent under the action of a chiral cobalt catalyst; in a chiral cobalt catalyst adopted by the method, when a chiral ligand is PAOR, an activating agent is NaBHEt3 or NaOtBu and an adopted raw material is aromatic ketone, the yield is 80% or above, and the optical purity is 90% or above; and when the adopted raw material is alkane ketone, the yield can reach 70% or above, and the optical purity can reach 80% or above.

Systems and methods for synthesizing chemical products, including active pharmaceutical ingredients


, (2020/12/14)

Systems and methods for synthesizing chemical products, including active pharmaceutical ingredients, are provided. Certain of the systems and methods described herein are capable of manufacturing multiple chemical products without the need to fluidically connect or disconnect unit operations when switching from one making chemical product to making another chemical product.

Copper-catalyzed and additive free decarboxylative trifluoromethylation of aromatic and heteroaromatic iodides

Johansen, Martin B.,Lindhardt, Anders T.

, p. 1417 - 1425 (2020/03/03)

A copper-catalyzed decarboxylative trifluoromethylation of (hetero)aromatic iodides has been developed. Importantly, this new copper-catalyzed reaction operates in the absence of any ligands and metal additives. The protocol shows good functional group tolerance and is compatible with heteroaromatic systems. The reaction proved scalable to a 15 mmol scale with increased yield. Finally, late-stage installation of the trifluoromethyl functionality afforded the N-trifluoroacetamide variant of the antidepressant agent, Prozac, demonstrating the applicability of the developed method.

Process route upstream and downstream products

Process route





Conditions Yield
3-methylamino-1-phenylpropan-1-ol; With sodium hydride; In dimethyl sulfoxide; at 60 ℃; for 1h; Inert atmosphere;
4-chlorobenzotrifluoride; In dimethyl sulfoxide; at 100 ℃; for 10h; Inert atmosphere;
With water; In diethyl ether; dimethyl sulfoxide;
3-methylamino-1-phenylpropan-1-ol; With sodium hydride; In dimethyl sulfoxide; at 60 ℃; for 1h;
4-chlorobenzotrifluoride; at 115 ℃; for 6h;
With potassium hydroxide; tetra(n-butyl)ammonium hydrogen sulfate; In sulfolane; water;
With 1-methyl-pyrrolidin-2-one; In water;
With 1-methyl-pyrrolidin-2-one; In water; toluene;
With 1-methyl-pyrrolidin-2-one; In water; toluene;
In water; toluene;
3-methylamino-1-phenylpropan-1-ol; With sodium hydride; In N,N-dimethyl acetamide; at 70 ℃; for 0.5h;
4-chlorobenzotrifluoride; In N,N-dimethyl acetamide; at 100 ℃; for 3h;
3-methylamino-1-phenylpropan-1-ol; With sodium hydride; In dimethyl sulfoxide; at 55 ℃; for 0.5h; Inert atmosphere;
4-chlorobenzotrifluoride; In dimethyl sulfoxide; at 90 ℃; for 1h;




Conditions Yield
With 18-crown-6 ether; potassium tert-butylate; In dimethyl sulfoxide; at 140 ℃; under 12153.3 - 12929 Torr; Molecular sieve;
tert-butyl methyl{3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl}carbamate

tert-butyl methyl{3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl}carbamate

Conditions Yield
With phosphoric acid; at 20 ℃; for 3h;
phenyl N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropyl-amine-N-carboxylate

phenyl N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropyl-amine-N-carboxylate

Conditions Yield
phenyl N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropyl-amine-N-carboxylate; With methylmagnesium chloride; In tetrahydrofuran; toluene; at 5 - 50 ℃;
With water; ammonium chloride; In tetrahydrofuran; toluene;
Conditions Yield
C20H22F3NO3; With methylmagnesium chloride; In tetrahydrofuran; toluene; at 5 - 50 ℃;
With water; ammonium chloride; In tetrahydrofuran; toluene;
Conditions Yield
With naphthalene; sodium; In 1,2-dimethoxyethane; at 20 ℃;


Conditions Yield
With potassium hydroxide; tetra(n-butyl)ammonium hydrogen sulfate; In sulfolane; water;
Multi-step reaction with 4 steps
1: triethylamine / dichloromethane / 1 h / 0 - 20 °C
2: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
3: copper(I) oxide / N,N-dimethyl-formamide / 24 h / 160 °C / 3300.33 Torr / Inert atmosphere; Sealed tube
4: sodium hydroxide / tetrahydrofuran / 5 h / 20 °C
With copper(I) oxide; di-isopropyl azodicarboxylate; triethylamine; triphenylphosphine; sodium hydroxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 2 h / 20 °C
2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 20 °C / Cooling with ice
3: phosphoric acid / 3 h / 20 °C
With di-isopropyl azodicarboxylate; phosphoric acid; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; 2: |Mitsunobu Displacement;




Conditions Yield
With tetra-(n-butyl)ammonium iodide; potassium carbonate; In methanol; at 80 ℃; for 24h; Sealed tube;
0.1 g


Conditions Yield
With sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 5h;




Conditions Yield
With tributylphosphine; di-isopropyl azodicarboxylate; In dichloromethane; N,N-dimethyl acetamide; at 70 ℃; for 0.0833333h;

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