Fluvoxamine

Title: Fluvoxamine
CAS Registry Number: 54739-18-3
CAS Name: (E)-5-Methoxy-1-[4-(trifluoromethyl)phenyl]-1-pentanone O-(2-aminoethyl)oxime
Additional Names: 5-methoxy-4¢-(trifluoromethyl)valerophenone (E)-O-(2-aminoethyl)oxime
Molecular Formula: C15H21F3N2O2
Molecular Weight: 318.33
Percent Composition: C 56.60%, H 6.65%, F 17.90%, N 8.80%, O 10.05%
Literature References: Selective serotonin reuptake inhibitor (SSRI). Prepn: NL 7503310; H. B. A. Welle, V. Claassen, US 4085225 (1975, 1978 both to Philips-Duphar). Inhibition of 5-HT uptake: V. Claassen et al., Br. J. Pharmacol. 60, 505 (1977). HPLC determn in plasma: G. J. De Jong, J. Chromatogr. 183, 203 (1980). Series of articles on pharmacology, pharmacokinetics and clinical trials in depression: Br. J. Clin. Pharmacol. 15, Suppl. 3, 347S-450S (1983). Clinical trial in obsessive-compulsive disorder: L. M. Koran et al., J. Clin. Psychopharmacol. 16, 121 (1996). Review of clinical experience in depression: M. R. Ware, J. Clin. Psychiatry 58, Suppl. 5, 15-23 (1997).
Derivative Type: Maleate
CAS Registry Number: 61718-82-9
Manufacturers' Codes: DU-23000; MK-264
Trademarks: Dumirox (Solvay); Faverin (Solvay); Fevarin (Solvay); Floxyfral (Solvay); Luvox (Solvay); Maveral (Farmades)
Molecular Formula: C15H21F3N2O2.C4H4O4
Molecular Weight: 434.41
Percent Composition: C 52.53%, H 5.80%, F 13.12%, N 6.45%, O 22.10%
Properties: Crystals from acetonitrile, mp 120-121.5°. Freely sol in ethanol, chloroform; sparingly sol in water. Practically insol in diethyl ether.
Melting point: mp 120-121.5°
Therap-Cat: Antidepressant; antiobsessional.
Keywords: Antidepressant; Antiobsessional; Serotonin Uptake Inhibitor.
FM1-43 Folescutol Folic Acid Folinic Acid Follicle-Stimulating Hormone

Fluvoxamine
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Systematic (IUPAC) name
2-{[(E)-{5-Methoxy-1-[4-(trifluoromethyl)phenyl]pentylidene}amino]oxy}ethanamine[1]
Clinical data
Trade names Luvox, Floxyfral, Fevarin
AHFS/Drugs.com monograph
MedlinePlus a682275
Pregnancy cat. C
Legal status Prescription Only (S4) (AU) -only (CA) POM (UK) -only (US)
Routes Oral
Pharmacokinetic data
Bioavailability 53% (90% confidence interval: 44-62%)[2]
Protein binding 80%[2]
Metabolism Hepatic (via cytochrome P450 enzymes. Mostly via oxidative demethylation)[2]
Half-life 12-13 hours (single dose), 22 hours (repeated dosing)[2]
Excretion Renal (98%; 94% as metabolites, 4% as unchanged drug)[2]
Identifiers
CAS number 54739-18-3 YesY
ATC code N06AB08
PubChem CID 5324346
DrugBank DB00176
ChemSpider 4481878 YesY
UNII O4L1XPO44W YesY
KEGG D07984 YesY
ChEBI CHEBI:5138 YesY
ChEMBL CHEMBL814 YesY
Chemical data
Formula C15H21F3N2O2 
Mol. mass 318.335
 N (what is this?)  (verify)

Fluvoxamine (brand names: Floxyfral, Luvox, Fevarin) is a medication which functions as a selective serotonin reuptake inhibitor (SSRI) and σ1 receptor agonist. Fluvoxamine is used primarily for the treatment of obsessive-compulsive disorder (OCD),[3] and is also used to treat major depressive disorder (MDD), and anxiety disorders such as panic disorder and posttraumatic stress disorder (PTSD).[4] Fluvoxamine CR (controlled release) is approved to treat social anxiety disorder.[5]

The FDA has added a black box warning for this drug in reference to increased risks of suicidal thinking and behavior in young adults and children. A study from the Institute for Safe Medication Practices identified reports of violence from those taking fluvoxamine as being 8.4 times higher than expected given the volume of overall reports for that drug. (Five reports of violence.)[6]