FLUPAROXAN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H10FNO2
Molecular Weight	195.1903
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12CNC[C@]1([H])OC3=C(O2)C=CC=C3F

InChI

InChIKey=XSOUHEXVEOQRKJ-IUCAKERBSA-N

InChI=1S/C10H10FNO2/c11-6-2-1-3-7-10(6)14-9-5-12-4-8(9)13-7/h1-3,8-9,12H,4-5H2/t8-,9-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C10H10FNO2
Molecular Weight	195.1903
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26996616 | https://www.ncbi.nlm.nih.gov/pubmed/1677298 | https://adisinsight.springer.com/drugs/800000678

Fluparoxan (GR50360A) is a potent α2-adrenergic receptor antagonist used in the treatment of central neurodegenerative diseases, depression, the improvement of cognitive dysfunction in schizophrenia and in models of Alzheimer's disease. Fluparoxan was undergoing phase III trials as an antidepressant, but this development was also discontinued because of poor efficacy.

Originator

Approval Year

PubMed

Title	Date	PubMed
A comparative study of the reversal by different alpha 2-adrenoceptor antagonists of the central sympatho-inhibitory effect of clonidine.	1996 Feb	8821553
Agonist and antagonist actions of yohimbine as compared to fluparoxan at alpha(2)-adrenergic receptors (AR)s, serotonin (5-HT)(1A), 5-HT(1B), 5-HT(1D) and dopamine D(2) and D(3) receptors. Significance for the modulation of frontocortical monoaminergic transmission and depressive states.	2000 Feb	10611634
Enhancing central noradrenergic function in depression: is there still a place for a new antidepressant?	2005 Mar	18568121
Unbiased descriptor and parameter selection confirms the potential of proteochemometric modelling.	2005 Mar 10	15760465
Alpha-2 adrenergic-induced changes in rectal temperature in adult and 13-day old rats following acute and repeated desipramine administration.	2008 Oct 2	18831759
The influence of serotonin- and other genes on impulsive behavioral aggression and cognitive impulsivity in children with attention-deficit/hyperactivity disorder (ADHD): Findings from a family-based association test (FBAT) analysis.	2008 Oct 20	18937842
A new strategy for antidepressant prescription.	2010	21151361

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:34:28 UTC 2023` Edited by `admin` on `Fri Dec 15 18:34:28 UTC 2023`
Record UNII	WGA8E072GX
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FLUPAROXAN

Official Name

English

1H-(1,4)BENZODIOXINO(2,3-C)PYRROLE, 5-FLUORO-2,3,3A,9A-TETRAHYDRO-, (3AS,9AS)-

Systematic Name

English

(3AS,9AS)-FLUPAROXAN

Common Name

English

(3AS,9AS)-5-FLUORO-2,3,3A,9A-TETRAHYDRO-1H-(1,4)BENZODIOXINO(2,3-C)PYRROLE

Common Name

English

Fluparoxan [WHO-DD]

Common Name

English

1H-(1,4)BENZODIOXINO(2,3-C)PYRROLE, 5-FLUORO-2,3,3A,9A-TETRAHYDRO-, (3AS-TRANS)-

Systematic Name

English

fluparoxan [INN]

Common Name

English

(-)-FLUPAROXAN

Common Name

English

FLUPAROXAN, (-)-

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID80146995