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Details

Stereochemistry ACHIRAL
Molecular Formula C15H21F3N2O2
Molecular Weight 318.3346
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of FLUVOXAMINE

SMILES

COCCCC\C(C1=CC=C(C=C1)C(F)(F)F)=N/OCCN

InChI

InChIKey=CJOFXWAVKWHTFT-XSFVSMFZSA-N
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/b20-14+

HIDE SMILES / InChI

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. The exact mechanism of action of fluvoxamine has not been fully determined, but appears to be linked to its inhibition of CNS neuronal uptake of serotonin. Fluvoxamine blocks the reuptake of serotonin at the serotonin reuptake pump of the neuronal membrane, enhancing the actions of serotonin on 5HT1A autoreceptors. In-vitro studies suggest that fluvoxamine is more potent than clomipramine, fluoxetine, and desipramine as a serotonin-reuptake inhibitor. Studies have also demonstrated that fluvoxamine has virtually no affinity for α1- or α2-adrenergic, β-adrenergic, muscarinic, dopamine D2, histamine H1, GABA-benzodiazepine, opiate, 5-HT1, or 5-HT2 receptors. Fluvoxamine is used for management of depression and for Obsessive Compulsive Disorder (OCD). Has also been used in the management of bulimia nervosa. Fluvoxamine is known under the brand names: Faverin, Fevarin, Floxyfral, Dumyrox and Luvox.

CNS Activity

Originator

Approval Year

TargetsConditions
PubMed

PubMed

TitleDatePubMed
Pharmacological profile of antidepressants and related compounds at human monoamine transporters.
1997 Dec 11
Pharmacological characterization and visualization of the glial serotonin transporter.
2001 Jul
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Patents

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Obsessive Compulsive Disorder Initial extended release capsule dose: 100 mg orally once a day at bedtime Initial immediate release tablet dose: 50 mg orally once a day at bedtime Maintenance dose: 100 to 300 mg orally per day. The dose may be increased in 50 mg increments every 4 to 7 days, as tolerated, until maximum therapeutic benefit is achieved. Maximum Dose: 300 mg orally per day
Route of Administration: Oral
In Vitro Use Guide
In the presence of 100 uM fluvoxamine, Kir4.1 currents heterologously expressed in HEK293T cells gradually increased during a hyperpolarizing step to −110 mV, and the outward current decreased rapidly during a depolarizing step to +30 mV
Name Type Language
FLUVOXAMINE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
FLUVOXAMINE [INN]
Common Name English
5-METHOXY-4'-(TRIFLUOROMETHYL)VALEROPHENONE (E)-O-(2-AMINOETHYL)OXIME
Systematic Name English
FLUVOXAMINE [WHO-DD]
Common Name English
1-PENTANONE, 5-METHOXY-1-(4-(TRIFLUOROMETHYL)PHENYL)-, O-(2-AMINOETHYL)OXIME, (1E)-
Systematic Name English
FLUVOXAMINE [VANDF]
Common Name English
FLUVOXAMINE [MI]
Common Name English
N06AB08
Code English
Classification Tree Code System Code
NDF-RT N0000175696
Created by admin on Tue Oct 22 00:25:46 UTC 2019 , Edited by admin on Tue Oct 22 00:25:46 UTC 2019
NDF-RT N0000000109
Created by admin on Tue Oct 22 00:25:46 UTC 2019 , Edited by admin on Tue Oct 22 00:25:46 UTC 2019
NCI_THESAURUS C265
Created by admin on Tue Oct 22 00:25:46 UTC 2019 , Edited by admin on Tue Oct 22 00:25:46 UTC 2019
WHO-ATC N06AB08
Created by admin on Tue Oct 22 00:25:46 UTC 2019 , Edited by admin on Tue Oct 22 00:25:46 UTC 2019
LIVERTOX 431
Created by admin on Tue Oct 22 00:25:46 UTC 2019 , Edited by admin on Tue Oct 22 00:25:46 UTC 2019
WHO-VATC QN06AB08
Created by admin on Tue Oct 22 00:25:46 UTC 2019 , Edited by admin on Tue Oct 22 00:25:46 UTC 2019
NCI_THESAURUS C94725
Created by admin on Tue Oct 22 00:25:46 UTC 2019 , Edited by admin on Tue Oct 22 00:25:46 UTC 2019
Code System Code Type Description
CAS
54739-18-3
Created by admin on Tue Oct 22 00:25:46 UTC 2019 , Edited by admin on Tue Oct 22 00:25:46 UTC 2019
PRIMARY
PUBCHEM
5324346
Created by admin on Tue Oct 22 00:25:46 UTC 2019 , Edited by admin on Tue Oct 22 00:25:46 UTC 2019
PRIMARY
WIKIPEDIA
FLUVOXAMINE
Created by admin on Tue Oct 22 00:25:46 UTC 2019 , Edited by admin on Tue Oct 22 00:25:46 UTC 2019
PRIMARY
RXCUI
42355
Created by admin on Tue Oct 22 00:25:46 UTC 2019 , Edited by admin on Tue Oct 22 00:25:46 UTC 2019
PRIMARY RxNorm
IUPHAR
7189
Created by admin on Tue Oct 22 00:25:46 UTC 2019 , Edited by admin on Tue Oct 22 00:25:46 UTC 2019
PRIMARY
MESH
D016666
Created by admin on Tue Oct 22 00:25:46 UTC 2019 , Edited by admin on Tue Oct 22 00:25:46 UTC 2019
PRIMARY
EVMPD
SUB07769MIG
Created by admin on Tue Oct 22 00:25:46 UTC 2019 , Edited by admin on Tue Oct 22 00:25:46 UTC 2019
PRIMARY
NCI_THESAURUS
C61769
Created by admin on Tue Oct 22 00:25:46 UTC 2019 , Edited by admin on Tue Oct 22 00:25:46 UTC 2019
PRIMARY
DRUG BANK
DB00176
Created by admin on Tue Oct 22 00:25:46 UTC 2019 , Edited by admin on Tue Oct 22 00:25:46 UTC 2019
PRIMARY
LactMed
54739-18-3
Created by admin on Tue Oct 22 00:25:46 UTC 2019 , Edited by admin on Tue Oct 22 00:25:46 UTC 2019
PRIMARY
ChEMBL
CHEMBL814
Created by admin on Tue Oct 22 00:25:46 UTC 2019 , Edited by admin on Tue Oct 22 00:25:46 UTC 2019
PRIMARY
MERCK INDEX
M5516
Created by admin on Tue Oct 22 00:25:46 UTC 2019 , Edited by admin on Tue Oct 22 00:25:46 UTC 2019
PRIMARY Merck Index
EPA CompTox
54739-18-3
Created by admin on Tue Oct 22 00:25:46 UTC 2019 , Edited by admin on Tue Oct 22 00:25:46 UTC 2019
PRIMARY
INN
3879
Created by admin on Tue Oct 22 00:25:46 UTC 2019 , Edited by admin on Tue Oct 22 00:25:46 UTC 2019
PRIMARY