FIPEXIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H21ClN2O4
Molecular Weight	388.845
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

ClC1=CC=C(OCC(=O)N2CCN(CC3=CC4=C(OCO4)C=C3)CC2)C=C1

InChI

InChIKey=BFUJHVVEMMWLHC-UHFFFAOYSA-N

InChI=1S/C20H21ClN2O4/c21-16-2-4-17(5-3-16)25-13-20(24)23-9-7-22(8-10-23)12-15-1-6-18-19(11-15)27-14-26-18/h1-6,11H,7-10,12-14H2

HIDE SMILES / InChI

Molecular Formula	C20H21ClN2O4
Molecular Weight	388.845
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6871040 | https://www.ncbi.nlm.nih.gov/pubmed/3519097 | https://www.ncbi.nlm.nih.gov/pubmed/6435653 | https://www.ncbi.nlm.nih.gov/pubmed/2260037 | https://www.ncbi.nlm.nih.gov/pubmed/1506632

Fipexide (aka attentil and vigilor) is a psychoactive drug of the piperazine class which was developed in Italy in 1983. It was used in Italy and France for the treatment of senile dementia but is no longer in common use due to undesirable side effects including fever and hepatitis.

CNS Activity

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Dementia 27 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3519097	Primary		Withdrawn	attentil Approved Use Previously Approved for use as a nootropic for the treatment of dementia; it has been withdrawn from the market.

PubMed

Title	Date	PubMed
Effects of methyl mercury, mercuric sulfide and cinnabar on active avoidance responses, Na+/K+-ATPase activities and tissue mercury contents in rats.	2001 Apr	11370760
Determining protein adducts of fipexide: mass spectrometry based assay for confirming the involvement of its reactive metabolite in covalent binding.	2007	18022964
Investigating the in vitro metabolism of fipexide: characterization of reactive metabolites using liquid chromatography/mass spectrometry.	2007	17577876
Metabolomics in drug intolerance.	2009 Nov	20214587
Development of a cell-based high-throughput assay to screen for inhibitors of organic anion transporting polypeptides 1B1 and 1B3.	2010 Mar 1	20448812
Improved detection of reactive metabolites with a bromine-containing glutathione analog using mass defect and isotope pattern matching.	2010 May 15	20391594
Palmitate increases the susceptibility of cells to drug-induced toxicity: an in vitro method to identify drugs with potential contraindications in patients with metabolic disease.	2012 Oct	22700542
Bioactivation of sitaxentan in liver microsomes, hepatocytes, and expressed human P450s with characterization of the glutathione conjugate by liquid chromatography tandem mass spectrometry.	2013 Jun 17	23721565

Patents

Sample Use Guides

In Vivo Use Guide

Geriatric patients received 600 mg fipexide daily for a period of 3 weeks. Treatment with fipexide was associated with a significant improvement in each and all monitored symptoms and signs to an average extent of 60%, relative to placebo. Overall, 85% of the patients given fipexide experienced clinical improvement to a greater or lesser degree.

Route of Administration: Oral

In Vitro Use Guide

Rat and human hepatocytes were incubated with 20 and 100 microM fipexide for 0, 2 and 6 hours at 30 deg-C. Samples were then quenched with equal volumes of ice-cold acetonitrile and centrifuged at 12000 rpm for 10 min at 4 deg-C. The supernatant was diluted 1:1 with water prior to injection into LC/MS to test whether the catechol metabolite or fipexide could be profiled for protein binding.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:24:16 GMT 2023` Edited by `admin` on `Fri Dec 15 16:24:16 GMT 2023`
Record UNII	TG44VME01D
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FIPEXIDE

Official Name

English

FIPEXIDE [MI]

Common Name

English

fipexide [INN]

Common Name

English

NSC-758407

Code

English

1-((P-CHLOROPHENOXY)ACETYL)-4-PIPERONYLPIPERAZINE

Common Name

English

Fipexide [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QN06BX05