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Fluvoxamine

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Fluvoxamine Basic information
Fluvoxamine Chemical Properties
  • Melting point:120-122.5°C
  • Boiling point:370.6±52.0 °C(Predicted)
  • Density 1.16±0.1 g/cm3(Predicted)
  • storage temp. -20°C Freezer, Under Inert Atmosphere
  • pkapKa 8.7 (Uncertain)
  • CAS DataBase Reference54739-18-3(CAS DataBase Reference)
  • NIST Chemistry ReferenceFluvoxamine(54739-18-3)
Fluvoxamine Usage And Synthesis
  • Chemical PropertiesColourless Oil
  • OriginatorFloxyfral, Kali-Duphar ,Switz. ,1983
  • UsesA selective serotonin reuptake inhibitor (SSRI) used as an anti-depressant
  • Manufacturing Process20.4 mmol (5.3 g) of 5-methoxy-4'-trifluoromethylvalerophenone (MP 43°C to 44°C), 20.5 mmol (3.1 g) of 2-aminooxyethylamine dihydrochloride and 10 ml of pyridine were refluxed for 15 hr in 20 ml of absolute ethanol. After evaporating the pyridine and the ethanol in vacuo, the residue was dissolved in water. This solution was washed with petroleum ether and 10 ml of 50% sodium hydroxide solution were then added. Then three extractions with 40 ml of ether were carried out. The ether extract was washed successively with 20 ml of 5% sodium bicarbonate solution and 20 ml of water. After drying on sodium sulfate, the ether layer was evaporated in vacuo. Toluene was then evaporated another three times (to remove the pyridine) and the oil thus obtained was dissolved in 15 ml of absolute ethanol. An equimolar quantity of maleic acid was added to the solution and the solution was then heated until a clear solution was obtained. The ethanol was then removed in vacuo and the residue was crystallized from 10 ml of acetonitrile at +5°C. After sucking off and washing with cold acetonitrile, it was dried in air. The MP of the resulting compound was 120°C to 121.5°C.
  • brand nameLuvox (Solvay Pharmaceuticals);Faverin.
  • Therapeutic FunctionAntidepressant
  • General DescriptionThe E-isomer of fluvoxamine (Luvox) can fold after protonation to the β-arylamine–like grouping. Here,the “extra” hydrophobic group is aliphatic.
  • HazardA poison.
  • Mechanism of actionFluvoxamine is a highly selective inhibitor of 5-HT reuptake at the presynaptic membrane. Potency data from in vitro affinity studies suggest that fluvoxamine is less potent than the other SSRIs (e.g., paroxetine, sertraline, and citalopram). Its mechanism of action is similar to that of the other SSRIs. Fluvoxamine appears to have little or no effect on the reuptake of NE or dopamine. In vitro studies have demonstrated that fluvoxamine possesses virtually no affinity for other neuroreceptors. Its onset of action is similar to the other SSRIs (2–4 weeks).
  • PharmacokineticsFluvoxamine is well absorbed, with a bioavailability of approximately 50%, probably because of first-pass metabolism. At steady-state doses, fluvoxamine demonstrates nonlinear pharmacokinetics over a dosage range of 100 to 300 mg/day, which results in higher plasma concentrations at higher doses than would be predicted by lower-dose kinetics (single dose, 15 hours; multiple dosing, 22 hours). Food does not significantly affect oral bioavailability. The mean apparent volume of distribution for fluvoxamine reflects its lipophilic nature, extensive tissue distribution, and protein binding. Fluvoxamine is distributed into breast milk. Fluvoxamine is preferentially metabolized by CYP2D6 in the liver by O-demethylation to its alcohol metabolite, which subsequently is oxidized to a carboxylic acid. Oxidative deamination and nine other metabolites have been identified, none of which shows significant pharmacological activity.
  • Clinical UseFluvoxamine is approved for use in obsessive-compulsive disorders.
  • Side effectsThe adverse effects for fluvoxamine include symptoms of drowsiness, nausea or vomiting, abdominal pain, tremors, sinus bradycardia, and mild anticholinergic symptoms. Toxic doses could produce seizures and severe bradycardia.
  • Drug interactionsIn vitro studies have shown fluvoxamine to be a potent inhibitor of CYP1A2, to inhibit CYP3A4 and CYP2C19, and to weakly inhibit CYP2D6. The bioavailability of fluvoxamine is significantly decreased in smokers compared with nonsmokers, possibly because of induction of CYP1A metabolism of fluvoxamine. Therefore, interactions with drugs that inhibit CYP1A2 also should be considered (e.g., theophylline and caffeine).
Fluvoxamine(54739-18-3)Related Product Information
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