NORFLUOXETINE

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 Search

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	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1715593
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27890559 | https://www.ncbi.nlm.nih.gov/pubmed/1415832 | https://www.ncbi.nlm.nih.gov/pubmed/15678084 | https://www.ncbi.nlm.nih.gov/pubmed/19014888

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

Primary Target	Pharmacology	Potency
Norepinephrine transporter 191 Target ID: CHEMBL222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19014888	Inhibitor 8297	2806.0 nM [IC50]
Dopamine transporter 180 Target ID: CHEMBL238 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19014888	Inhibitor 8297	6488.0 nM [IC50]
Serotonin transporter 178 Target ID: CHEMBL228 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19014888	Inhibitor 8297	46.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Determination of fluoxetine and norfluoxetine in human plasma by high-pressure liquid chromatography with fluorescence detection.	1998 Oct	9863958
Evidence for possible involvement of 5-HT(2B) receptors in the cardiac valvulopathy associated with fenfluramine and other serotonergic medications.	2000 Dec 5	11104741
Effect of alosetron on the pharmacokinetics of fluoxetine.	2001 Apr	11304903
Cytochrome P450 2D6.1 and cytochrome P450 2D6.10 differ in catalytic activity for multiple substrates.	2001 Aug	11505218
Effects of norfluoxetine, the major metabolite of fluoxetine, on the cloned neuronal potassium channel Kv3.1.	2001 Sep	11543764
Expression, purification, biochemical characterization, and comparative function of human cytochrome P450 2D6.1, 2D6.2, 2D6.10, and 2D6.17 allelic isoforms.	2002 Dec	12438554
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	12584149
The effects of desmethylimipramine on cyclic AMP-stimulated gene transcription in a model cell system.	2005 Sep 1	16036225
[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	16856516
Drug-induced long QT syndrome: hERG K+ channel block and disruption of protein trafficking by fluoxetine and norfluoxetine.	2006 Nov	16967046
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	18083778

Patents

Sample Use Guides

In Vivo Use Guide

Rats were treated with Norfluoxetine (0-20mg/kg)

Route of Administration: Other

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 `Sat Dec 16 06:50:20 UTC 2023` Edited by `admin` on `Sat Dec 16 06:50:20 UTC 2023`
Record UNII	K8D70XE2F4
Record Status	`Validated (UNII)`
Record Version

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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