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Details

Stereochemistry ACHIRAL
Molecular Formula C15H21F3N2O2.C4H4O4
Molecular Weight 434.4068
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of FLUVOXAMINE MALEATE

SMILES

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

InChI

InChIKey=LFMYNZPAVPMEGP-PIDGMYBPSA-N
InChI=1S/C15H21F3N2O2.C4H4O4/c1-21-10-3-2-4-14(20-22-11-9-19)12-5-7-13(8-6-12)15(16,17)18;5-3(6)1-2-4(7)8/h5-8H,2-4,9-11,19H2,1H3;1-2H,(H,5,6)(H,7,8)/b20-14+;2-1-

HIDE SMILES / InChI

Molecular Formula C15H21F3N2O2
Molecular Weight 318.3346
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:25:43 UTC 2019
Edited
by admin
on Tue Oct 22 00:25:43 UTC 2019
Record UNII
5LGN83G74V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FLUVOXAMINE MALEATE
EP   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
FLUVOXAMINE MALEATE [WHO-DD]
Common Name English
FLUVOXAMINE MALEATE [EP]
Common Name English
FLUVOXAMINE MALEATE [MART.]
Common Name English
FLUVOXAMINE MALEATE [VANDF]
Common Name English
FLUVOXAMINE MALEATE [USP]
Common Name English
FLUVOXAMINE MALEATE [MI]
Common Name English
FLUVOXAMINE MALEATE [USAN]
Common Name English
FLUVOXAMINE MALEATE [ORANGE BOOK]
Common Name English
DU-23000
Code English
5-METHOXY-4'-(TRIFLUOROMETHYL)VALEROPHENONE-(E)-O-(2-AMINOETHYL)OXIME MALEATE (1:1)
Systematic Name English
1-PENTANONE, 5-METHOXY-1-(4-(TRIFLUOROMETHYL)PHENYL)-, O-(2-AMINOETHYL)OXIME, (E)-, (Z)-2-BUTENEDIOATE (1:1)
Common Name English
DU23000
Code English
LUVOX
Brand Name English
FLUVOXAMINE MALEATE [USP-RS]
Common Name English
FLUVOXAMINE MALEATE [JAN]
Common Name English
FLUVOXAMINE HYDROGENMALEATE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C94725
Created by admin on Tue Oct 22 00:25:44 UTC 2019 , Edited by admin on Tue Oct 22 00:25:44 UTC 2019
NCI_THESAURUS C265
Created by admin on Tue Oct 22 00:25:44 UTC 2019 , Edited by admin on Tue Oct 22 00:25:44 UTC 2019
Code System Code Type Description
PUBCHEM
9560989
Created by admin on Tue Oct 22 00:25:44 UTC 2019 , Edited by admin on Tue Oct 22 00:25:44 UTC 2019
PRIMARY
EPA CompTox
61718-82-9
Created by admin on Tue Oct 22 00:25:44 UTC 2019 , Edited by admin on Tue Oct 22 00:25:44 UTC 2019
PRIMARY
RXCUI
203143
Created by admin on Tue Oct 22 00:25:44 UTC 2019 , Edited by admin on Tue Oct 22 00:25:44 UTC 2019
PRIMARY RxNorm
NCI_THESAURUS
C29063
Created by admin on Tue Oct 22 00:25:44 UTC 2019 , Edited by admin on Tue Oct 22 00:25:44 UTC 2019
PRIMARY
CAS
61718-82-9
Created by admin on Tue Oct 22 00:25:44 UTC 2019 , Edited by admin on Tue Oct 22 00:25:44 UTC 2019
PRIMARY
ChEMBL
CHEMBL814
Created by admin on Tue Oct 22 00:25:44 UTC 2019 , Edited by admin on Tue Oct 22 00:25:44 UTC 2019
PRIMARY
MERCK INDEX
M5516
Created by admin on Tue Oct 22 00:25:44 UTC 2019 , Edited by admin on Tue Oct 22 00:25:44 UTC 2019
PRIMARY Merck Index
EVMPD
SUB13908MIG
Created by admin on Tue Oct 22 00:25:44 UTC 2019 , Edited by admin on Tue Oct 22 00:25:44 UTC 2019
PRIMARY
EVMPD
SUB16363MIG
Created by admin on Tue Oct 22 00:25:44 UTC 2019 , Edited by admin on Tue Oct 22 00:25:44 UTC 2019
PRIMARY
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