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Details

Stereochemistry RACEMIC
Molecular Formula C16H16F3NO
Molecular Weight 295.2995
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NORFLUOXETINE

SMILES

NCCC(OC1=CC=C(C=C1)C(F)(F)F)C2=CC=CC=C2

InChI

InChIKey=WIQRCHMSJFFONW-UHFFFAOYSA-N
InChI=1S/C16H16F3NO/c17-16(18,19)13-6-8-14(9-7-13)21-15(10-11-20)12-4-2-1-3-5-12/h1-9,15H,10-11,20H2

HIDE SMILES / InChI

Molecular Formula C16H16F3NO
Molecular Weight 295.2995
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Norfluoxetine is an active N-desmethyl metabolite of the antidepressant fluoxetine that inhibits serotonin uptake. Norfluoxetine is selective serotonin reuptake inhibitor (SSRI) but little is known about its pharmacological actions. Seproxetine (S- Norfluoxetine) was being investigated by Eli Lilly as an antidepressant but development was never completed and the drug was never marketed.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
46.0 nM [IC50]
6488.0 nM [IC50]
2806.0 nM [IC50]
PubMed

PubMed

TitleDatePubMed
Determination of fluoxetine and norfluoxetine in human plasma by high-pressure liquid chromatography with fluorescence detection.
1998 Oct
Evidence for possible involvement of 5-HT(2B) receptors in the cardiac valvulopathy associated with fenfluramine and other serotonergic medications.
2000 Dec 5
Effect of alosetron on the pharmacokinetics of fluoxetine.
2001 Apr
Cytochrome P450 2D6.1 and cytochrome P450 2D6.10 differ in catalytic activity for multiple substrates.
2001 Aug
Effects of norfluoxetine, the major metabolite of fluoxetine, on the cloned neuronal potassium channel Kv3.1.
2001 Sep
Expression, purification, biochemical characterization, and comparative function of human cytochrome P450 2D6.1, 2D6.2, 2D6.10, and 2D6.17 allelic isoforms.
2002 Dec
Assessment of the contributions of CYP3A4 and CYP3A5 in the metabolism of the antipsychotic agent haloperidol to its potentially neurotoxic pyridinium metabolite and effect of antidepressants on the bioactivation pathway.
2003 Mar
The effects of desmethylimipramine on cyclic AMP-stimulated gene transcription in a model cell system.
2005 Sep 1
[Trazodone for the treatment of behavioral and psychological symptoms of dementia (BPSD) in Alzheimer's disease: a retrospective study focused on the aggression and negativism in caregiving situations].
2006 Jun
Drug-induced long QT syndrome: hERG K+ channel block and disruption of protein trafficking by fluoxetine and norfluoxetine.
2006 Nov
Inverse agonist and neutral antagonist actions of antidepressants at recombinant and native 5-hydroxytryptamine2C receptors: differential modulation of cell surface expression and signal transduction.
2008 Mar
Patents

Sample Use Guides

In Vivo Use Guide
Rats were treated with Norfluoxetine (0-20mg/kg)
Route of Administration: Intraperitoneal; Subcutanious
In Vitro Use Guide
Rat cortical membranes equivalent to 50 mkg of protein were incubated at 37°C for 30 minutes in 2 ml of reaction medium containing the Norfluoxetine (1-1000nM), 0.1 nM [3Hlparoxetine, 50 mmol/L Tris-HG, pH 7.4, 150 mmol/L NaG, and 5 mmol/L KCl. Fluoxetine at 1 mkM/kg was used to determine nonspecific binding
Substance Class Chemical
Created
by admin
on Tue Oct 22 15:42:39 UTC 2019
Edited
by admin
on Tue Oct 22 15:42:39 UTC 2019
Record UNII
K8D70XE2F4
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NORFLUOXETINE
Common Name English
BENZENEPROPANAMINE, .GAMMA.-(4-(TRIFLUOROMETHYL)PHENOXY)-, (+/-)-
Systematic Name English
DESMETHYLFLUOXETINE
Common Name English
(+/-)-DESMETHYLFLUOXETINE
Common Name English
Code System Code Type Description
MESH
C036139
Created by admin on Tue Oct 22 15:42:39 UTC 2019 , Edited by admin on Tue Oct 22 15:42:39 UTC 2019
PRIMARY
WIKIPEDIA
Norfluoxetine
Created by admin on Tue Oct 22 15:42:39 UTC 2019 , Edited by admin on Tue Oct 22 15:42:39 UTC 2019
PRIMARY
CAS
83891-03-6
Created by admin on Tue Oct 22 15:42:39 UTC 2019 , Edited by admin on Tue Oct 22 15:42:39 UTC 2019
PRIMARY
EVMPD
SUB32375
Created by admin on Tue Oct 22 15:42:39 UTC 2019 , Edited by admin on Tue Oct 22 15:42:39 UTC 2019
PRIMARY
PUBCHEM
4541
Created by admin on Tue Oct 22 15:42:39 UTC 2019 , Edited by admin on Tue Oct 22 15:42:39 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> METABOLITE ACTIVE
CYP2D6 enzyme is involved in the metabolism of fluoxetine to norfluoxetine in patients under steady-state conditions