Fluvoxamine
- CAS No.
- 54739-18-3
- Chemical Name:
- Fluvoxamine
- Synonyms
- FLUVOXAMINE;Fluvoxamine USP/EP/BP;Fluvoxamine Impurity 7;Fluvoxamine See: F603500;Fluvoxamine Also See: F603500 ;δ-Methoxy-4'-(trifluoromethyl)valerophenone (E)-O-(2-aminoethyl)oxime;(E)-ω-Methoxy-4'-(trifluoromethyl)valerophenone O-(2-aminoethyl)oxime;(1E)-5-Methoxy-1-[4-(trifluoromethyl)phenyl]pentanal O-(2-aminoethyl)oxime;2-[[5-methoxy-1-[4-(trifluoromethyl)phenyl]-pentylidene]amino]oxyethanamine;(E)-5-methoxy-1-[4-(trifluoromethyl)phenyl]-1-pentanoneo-(2-aminoethyl)oxime
- CBNumber:
- CB8468990
- Molecular Formula:
- C15H21F3N2O2
- Molecular Weight:
- 318.33
- MOL File:
- 54739-18-3.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/3/29 23:06:43
| Melting point | 120-122.5°C |
|---|---|
| Boiling point | 370.6±52.0 °C(Predicted) |
| Density | 1.16±0.1 g/cm3(Predicted) |
| storage temp. | Sealed in dry,2-8°C |
| solubility | Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly) |
| form | Oil |
| pka | pKa 8.7 (Uncertain) |
| color | Colourless |
| CAS DataBase Reference | 54739-18-3(CAS DataBase Reference) |
| NIST Chemistry Reference | Fluvoxamine(54739-18-3) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |    GHS07,GHS09,GHS06 |
|---|---|
| Signal word | Danger |
| Hazard statements | H302-H335-H331-H410-H319 |
| Precautionary statements | P273-P391-P501-P264-P280-P305+P351+P338-P337+P313P-P261-P271-P304+P340-P311-P321-P403+P233-P405-P501-P264-P270-P301+P312-P330-P501 |
Fluvoxamine Chemical Properties,Uses,Production
Chemical Properties
Colourless Oil
General Description
The E-isomer of fluvoxamine (Luvox) can fold after protonation to the β-arylamine–like grouping. Here,the “extra” hydrophobic group is aliphatic.
Hazard
A poison.
Mechanism of action
Fluvoxamine 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).
Pharmacokinetics
Fluvoxamine 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 Use
Fluvoxamine is approved for use in obsessive-compulsive disorders.
Side effects
The 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 interactions
In 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 Preparation Products And Raw materials
Raw materials
Preparation Products
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