(E)-(2-aminoethoxy)({5-methoxy-1-[4-(trifluoromethyl)phenyl]pentylidene})amine

• ChemBase ID: 61
• Molecular Formular: C15H21F3N2O2
• Molecular Mass: 318.3346496
• Monoisotopic Mass: 318.15551258
• SMILES: FC(F)(F)c1ccc(/C(=N/OCCN)/CCCCOC)cc1
• Canonical SMILES: NCCO/N=C(/c1ccc(cc1)C(F)(F)F)\CCCCOC
• InChI: InChI=1S/C15H21F3N2O2/c1-21-10-3-2-4-14(20-22-11-9-19)12-5-7-13(8-6-12)15(16,17)18/h5-8H,2-4,9-11,19H2,1H3
• InChIKey: CJOFXWAVKWHTFT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (E)-(2-aminoethoxy)({5-methoxy-1-[4-(trifluoromethyl)phenyl]pentylidene})amine; (2-aminoethoxy)({5-methoxy-1-[4-(trifluoromethyl)phenyl]pentylidene})amine
• IUPAC Traditional name: fluvoxamine; luvox
• Brand Name: Dumirox; Faverin; Fevarin; Floxyfral; Luvox; Maveral; Dumyrox; Luvox, Floxyfral
• Synonyms: (E)-5-(Methoxy-d3)-1-[4-(triflurormethyl)phenyl]-1-pentanone O-(2-Aminoethyl)oxime; FluvoxamineAlso See: F603500; (E)-5-Methoxy-1-(4-(trifluoroMethyl)phenyl)pentan-1-one O-(2-aMinoethyl) oxiMe; Fluvoxamina [INN-Spanish]; Fluvoxamine maleate; Fluvoxaminum [INN-Latin]; fluvoxamine; fluvoxamine-CR; Fluvoxamine

Database IDs

• CAS Number: 54739-18-3
• PubChem SID: 160963524; 46507588
• PubChem CID: 5324346
• CHEBI ID: 5138
• ATC CODE: N06AB08
• CHEMBL: 814
• Chemspider ID: 4481878
• DrugBank ID: DB00176
• KEGG ID: D07984
• Unique Ingredient Identifier: O4L1XPO44W
• Wikipedia Title: Fluvoxamine
• Medline Plus: a682275

CALCULATED PROPERTIES

JChem

• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.14645693
• LogD (pH = 7.4): 1.0475725
• Log P: 2.7953196
• Molar Refractivity: 79.1971 cm^3
• Polarizability: 29.756128 Å^3
• Polar Surface Area: 56.84 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.89
• LOG S: -4.64
• Solubility (Water): 7.34e-03 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Petroleum Ether
• Apperance: Colourless Oil
• Hydrophobicity(logP): 3.2

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: 77%
• Excretion: Renal
• Half Life: 15.6 hours
• Metabolism: Hepatic
• Legal Status: Rx-only (US); S4 (Australia)
• Pregnancy Category: C

Product Information

• Purity: 97%

DETAILS

DrugBank - DB00176

• Drug Groups: approved; investigational
• Description: Fluvoxamine is an antidepressant which functions pharmacologically as a selective serotonin reuptake inhibitor. Though it is in the same class as other SSRI drugs, it is most often used to treat obsessive-compulsive disorder.; Fluvoxamine has been in use in clinical practice since 1983 and has a clinical trial database comprised of approximately 35,000 patients. It was launched in the US in December 1994 and in Japan in June 1999. As of the end of 1995, more than 10 million patients worldwide have been treated with fluvoxamine.
• Indication: For management of depression and for Obsessive Compulsive Disorder (OCD). Has also been used in the management of bulimia nervosa.
• Pharmacology: Fluvoxamine, an aralkylketone-derivative agent, is one of a class of antidepressants known as selective serotonin reuptake inhibitors (SSRIs) that differs structurally from other SSRIs. It is used to treat the depression associated with mood disorders. It is also used on occassion in the treatment of body dysmorphic disorder and anxiety. The antidepressant, antiobsessive-compulsive, and antibulimic actions of Fluvoxamine are presumed to be linked to its inhibition of CNS neuronal uptake of serotonin. In vitro studies show that Fluvoxamine is a potent and selective inhibitor of neuronal serotonin reuptake and has only very weak effects on norepinephrine and dopamine neuronal reuptake. Fluvoxamine has no significant affinity for adrenergic (alpha1, alpha2, beta), cholinergic, GABA, dopaminergic, histaminergic, serotonergic (5HT_1A, 5HT_1B, 5HT₂), or benzodiazepine receptors; antagonism of such receptors has been hypothesized to be associated with various anticholinergic, sedative, and cardiovascular effects for other psychotropic drugs. The chronic administration of Fluvoxamine was found to downregulate brain norepinephrine receptors, as has been observed with other drugs effective in the treatment of major depressive disorder. Fluvoxamine does not inhibit monoamine oxidase.
• Toxicity: Side effects include anorexia, constipation, dry mouth, headache, nausea, nervousness, skin rash, sleep problems, somnolence, liver toxicity, mania, increase urination, seizures, sweating increase, tremors, or Tourette's syndrome.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Well absorbed, bioavailability of fluvoxamine maleate is 53%.
• Half Life: 15.6 hours
• Protein Binding: ~77-80% (plasma protein)
• Elimination: The main human metabolite was fluvoxamine acid which, together with its N-acetylated analog, accounted for about 60% of the urinary excretion products. Approximately 2% of fluvoxamine was excreted in urine unchanged. Following a 14C-labelled oral dose of fluvoxamine maleate (5 mg), an average of 94% of drug-related products was recovered in the urine within 71 hours.
• Distribution: * 25 L/kg
• References: Dell'Osso B, Allen A, Hollander E: Fluvoxamine: a selective serotonin re-uptake inhibitor for the treatment of obsessive-compulsive disorder. Expert Opin Pharmacother. 2005 Dec;6(15):2727-40. [Pubmed] ; Irons J: Fluvoxamine in the treatment of anxiety disorders. Neuropsychiatr Dis Treat. 2005 Dec;1(4):289-99. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Toronto Research Chemicals - F603501

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

REFERENCES

• Dell'Osso B, Allen A, Hollander E: Fluvoxamine: a selective serotonin re-uptake inhibitor for the treatment of obsessive-compulsive disorder. Expert Opin Pharmacother. 2005 Dec;6(15):2727-40. Pubmed
• Irons J: Fluvoxamine in the treatment of anxiety disorders. Neuropsychiatr Dis Treat. 2005 Dec;1(4):289-99. Pubmed
• Claassen, V., et al.: Br. J. Pharmacol., 60, 505 (1977)
• Koran, L.M., et al.: J. Clin. Psychopharmacol., 16, 121 (1977)
• Ware, M.R., et al.: J. Clin. Psychiatry, 58, Suppl. 5, 15 (1977)
• Inazu, M., et al.: Neurochem. Int., 39, 39 (2001).