SEPROXETINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H16F3NO
Molecular Weight	295.2995
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NCC[C@H](OC1=CC=C(C=C1)C(F)(F)F)C2=CC=CC=C2

InChI

InChIKey=WIQRCHMSJFFONW-HNNXBMFYSA-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/t15-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C16H16F3NO
Molecular Weight	295.2995
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1279447
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/15886723 | https://www.ncbi.nlm.nih.gov/pubmed/10208643 | https://www.ncbi.nlm.nih.gov/pubmed/8512621

Seproxetine, also known as (S)-norfluoxetine, is a selective serotonin reuptake inhibitor (SSRI). It is the most important active metabolite of the widely used antidepressant fluoxetine, but little is known about its pharmacological actions. Seproxetine was being investigated by Eli Lilly and Company as an antidepressant; however, a cardiac side effect was noted and development was discontinued.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Dopamine transporter 180 Target ID: CHEMBL238 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19014888	Inhibitor 8297	4544.0 nM [Ki]
Norepinephrine transporter 191 Target ID: CHEMBL222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19014888	Inhibitor 8297	6186.0 nM [Ki]
Serotonin transporter 178 Target ID: CHEMBL228 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19014888	Inhibitor 8297	50.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed

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 (S)-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 `Fri Dec 15 16:01:31 UTC 2023` Edited by `admin` on `Fri Dec 15 16:01:31 UTC 2023`
Record UNII	25CO3X0R31
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SEPROXETINE

Official Name

English

NORFLUOXETINE, (S)-

Common Name

English

(S)-NORFLUOXETINE

Common Name

English

seproxetine [INN]

Common Name

English

BENZENEPROPANAMINE, .GAMMA.-(4-(TRIFLUOROMETHYL)PHENOXY)-, (.GAMMA.S)-

Systematic Name

English

Seproxetine [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C265