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54739-18-3 molecular structure
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(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 and InChIs

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

Cite this record

CBID:61 http://www.chembase.cn/molecule-61.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2-aminoethoxy)({5-methoxy-1-[4-(trifluoromethyl)phenyl]pentylidene})amine
(E)-(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
Fluvoxamina [INN-Spanish]
Fluvoxamine maleate
Fluvoxaminum [INN-Latin]
fluvoxamine
fluvoxamine-CR
(E)-5-(Methoxy-d3)-1-[4-(triflurormethyl)phenyl]-1-pentanone O-(2-Aminoethyl)oxime
Fluvoxamine
(E)-5-Methoxy-1-(4-(trifluoroMethyl)phenyl)pentan-1-one O-(2-aMinoethyl) oxiMe
FluvoxamineAlso See: F603500
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) -0.14645693  LogD (pH = 7.4) 1.0475725 
Log P 2.7953196  Molar Refractivity 79.1971 cm3
Polarizability 29.756128 Å3 Polar Surface Area 56.84 Å2
Rotatable Bonds 10  Lipinski's Rule of Five true 
Log P 2.89  LOG S -4.64 
Solubility (Water) 7.34e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Dichloromethane expand Show data source
Petroleum Ether expand Show data source
Apperance
Colourless Oil expand Show data source
Hydrophobicity(logP)
3.2 expand Show data source
Storage Condition
-20°C Freezer, Under Inert Atmosphere expand Show data source
MSDS Link
Download expand Show data source
Admin Routes
Oral expand Show data source
Bioavailability
77% expand Show data source
Excretion
Renal expand Show data source
Half Life
15.6 hours expand Show data source
Metabolism
Hepatic expand Show data source
Legal Status
Rx-only (US) expand Show data source
S4 (Australia) expand Show data source
Pregnancy Category
C expand Show data source
Purity
97% expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia TRC TRC
DrugBank - DB00176 external link
Item Information
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 (5HT1A, 5HT1B, 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 external link
A selective serotonin reuptake inhibitor (SSRI) used as an anti-depressant.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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).
  • • 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
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PATENTS

PATENTS

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