Fluvoxamine maleate Chemical Properties

Melting point:

120-121.5 °C

Flash point:

9℃

storage temp. 

2-8°C

solubility 

H₂O: soluble

form 

solid

color 

White to Off-White

Water Solubility 

Soluble in water (10mM)

Merck 

14,4219

BCS Class

1

InChIKey

LFMYNZPAVPMEGP-PIDGMYBPSA-N

SMILES

C(C1C=CC(=CC=1)/C(=N\OCCN)/CCCCOC)(F)(F)F.C(O)(=O)/C=C\C(O)=O

CAS DataBase Reference

61718-82-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

36-36/37/39-27-26

RIDADR 

UN1230 - class 3 - PG 2 - Methanol, solution

WGK Germany 

3

RTECS 

SA9230000

HS Code 

29280000

MSDS

• Language:English Provider:SigmaAldrich

Fluvoxamine maleate Usage And Synthesis

Description

Fluvoxamine maleate is the most recent of the serotonin-specific antidepressants to reach the market. In vitro and in vivo animal experiments have shown fluvoxamine to have a marked effect on 5-HT mediated processes and little effect on norepinephrine. Clinical trials suggest similar efficacy to imipramine and clomipramine with a somewhat lower incidence of side effects, especially anticholinergic effects. Fluvoxamine, in contrast to the tricyclic antidepressants, does not appear to produce heart rate increase, postural hypotension or prolongation of the intraventricular conduction time and QT interval.

Chemical Properties

Crystalline Solid

Originator

Duphar (Netherlands)

Uses

A selective serotonin reuptake inhibitor (SSRI) used as an anti-depressant. Antiobsessional.

Uses

estrogen

Uses

nonsteroidal anti-inflammatory reduces pain and inflammation in eyes

Uses

Anxiety disorder

Uses

Fluvoxamine maleate has been used as a test compound to determine the solubility and effective blood-brain barrier permeability.(2)

Definition

ChEBI: Fluvoxamine maleate is a member of (trifluoromethyl)benzenes.

Manufacturing Process

20.4 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 name

Luvox (Solvay Pharmaceuticals);FLOXYFRAL.

Therapeutic Function

Antidepressant

General Description

Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards

Hazard

A poison by ingestion. Human systemic effects.

Biological Activity

Selective serotonin reuptake inhibitor; antidepressant. Binds to the human 5-HT transporter with a K i of 1.6 nmol/l. Also available as part of the Serotonin Uptake Inhibitor Tocriset™ .

Biochem/physiol Actions

Fluvoxamine maleate is a selective neuronal serotonin reuptake inhibitor. It functions as an antidepressant and anti-obsessive agent. It is useful in treating obsessive compulsive disorder and panic disorder.

Clinical Use

SSRI antidepressant:
Depression
Obsessive compulsive disorder

Veterinary Drugs and Treatments

Fluvoxamine may be considered for use in treating a variety of behavior- related diagnoses in dogs and cats, including aggression and stereotypic behaviors (and other obsessive-compulsive behaviors).

Drug interactions

Potentially hazardous interactions with other drugs
Aminophylline and theophylline: increased aminophylline and theophylline concentrations - avoid; if not possible, halve aminophylline or theophylline dose and monitor levels.
Analgesics: increased risk of bleeding with aspirin and NSAIDs; risk of CNS toxicity increased with tramadol; concentration of methadone possibly increased.
Anti-arrhythmics: increased risk of toxicity with mexiletine.
Anticoagulants: effect of coumarins possibly enhanced; possibly increased risk of bleeding with dabigatran.
Antidepressants: avoid with reboxetine, MAOIs, moclobemide and St John’s wort; possibly enhanced serotonergic effects with mirtazapine; fluvoxamine inhibits metabolism of duloxetine - avoid; can increase tricyclics concentration; metabolism of agomelatine reduced; possible increased risk of convulsions with vortioxetine.
Antiepileptics: antagonise anticonvulsant threshold; concentration of carbamazepine, fosphenytoin and phenytoin increased.
Antimalarials: avoid with artemether/lumefantrine and piperaquine with artenimol.
Antipsychotics: concentration of asenapine, haloperidol, clozapine and olanzapine increased; increased risk of ventricular arrhythmias with droperidol and possibly pimozide - avoid.
Antivirals: concentration possibly increased by ritonavir.
Ciclosporin: may increase ciclosporin concentration.
Clopidogrel: possibly reduced antiplatelet effect.
Cytotoxics: concentration of pomalidomide increased
Dapoxetine: possible increased risk of serotonergic effects - avoid.
Dopaminergics: increased risk of CNS toxicity with rasagiline - avoid; hypertension and CNS excitation with selegiline - avoid.
5HT1 agonists: risk of CNS toxicity increased with sumatriptan; possibly increased risk of serotonergic effects with naratriptan; inhibits metabolism of frovatriptan; possibly inhibits metabolism of zolmitriptan - reduce zolmitriptan dose.
Linezolid: use with care, possibly increased risk of side effects.
Lithium: increased risk of CNS effects - monitor levels.
Melatonin: concentration of melatonin increased - avoid.
Methylthioninium: risk of CNS toxicity - avoid if possible.
Muscle relaxants: increased risk of toxicity with tizanidine - avoid
Pirfenidone: concentration of pirfenidone increased - avoid.

Metabolism

Fluvoxamine undergoes extensive hepatic transformation by CYP2D6, mainly via oxidative demethylation, into at least 9 metabolites. The 2 major metabolites showed negligible pharmacological activity. The other metabolites are not expected to be pharmacologically active.
Excretion is mainly in the urine; about 2% of a dose is excreted as unchanged drug.

storage

+4°C (desiccate)

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