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Details

Stereochemistry ACHIRAL
Molecular Formula C20H21ClN2O4.ClH
Molecular Weight 425.306
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FIPEXIDE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=MVOWQBJZZKOQNU-UHFFFAOYSA-N
InChI=1S/C20H21ClN2O4.ClH/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;1H

HIDE SMILES / InChI
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.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
attentil

Approved Use

Previously Approved for use as a nootropic for the treatment of dementia; it has been withdrawn from the market.
PubMed

PubMed

TitleDatePubMed
Determining protein adducts of fipexide: mass spectrometry based assay for confirming the involvement of its reactive metabolite in covalent binding.
2007
Metabolomics in drug intolerance.
2009 Nov
Development of a cell-based high-throughput assay to screen for inhibitors of organic anion transporting polypeptides 1B1 and 1B3.
2010 Mar 1
Improved detection of reactive metabolites with a bromine-containing glutathione analog using mass defect and isotope pattern matching.
2010 May 15
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
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
Patents

Sample Use Guides

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
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.
Name Type Language
FIPEXIDE HYDROCHLORIDE
MART.   MI   WHO-DD  
Common Name English
ETHANONE, 1-(4-(1,3-BENZODIOXOL-5-YLMETHYL)-1-PIPERAZINYL)-2-(4-CHLOROPHENOXY)-, HYDROCHLORIDE (1:1)
Systematic Name English
FIPEXIDE HYDROCHLORIDE [MI]
Common Name English
VIGILOR
Brand Name English
1-(4-CHLOROPHENOXYACETYL)-4-PIPERONYLPIPERAZINE HYDROCHLORIDE
Systematic Name English
PIPERAZINE, 1-(1,3-BENZODIOXOL-5-YLMETHYL)-4-((4-CHLOROPHENOXY)ACETYL)-, MONOHYDROCHLORIDE
Common Name English
Fipexide hydrochloride [WHO-DD]
Common Name English
BP-662
Common Name English
BP 662
Code English
FIPEXIDUM HYDROCHLORIDE
Common Name English
FIPEXIDE HYDROCHLORIDE [MART.]
Common Name English
Code System Code Type Description
ECHA (EC/EINECS)
251-856-9
Created by admin on Fri Dec 15 18:22:49 GMT 2023 , Edited by admin on Fri Dec 15 18:22:49 GMT 2023
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EVMPD
SUB02193MIG
Created by admin on Fri Dec 15 18:22:49 GMT 2023 , Edited by admin on Fri Dec 15 18:22:49 GMT 2023
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CAS
34161-23-4
Created by admin on Fri Dec 15 18:22:49 GMT 2023 , Edited by admin on Fri Dec 15 18:22:49 GMT 2023
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EPA CompTox
DTXSID6047446
Created by admin on Fri Dec 15 18:22:49 GMT 2023 , Edited by admin on Fri Dec 15 18:22:49 GMT 2023
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FDA UNII
NQ702L425I
Created by admin on Fri Dec 15 18:22:49 GMT 2023 , Edited by admin on Fri Dec 15 18:22:49 GMT 2023
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PUBCHEM
161803
Created by admin on Fri Dec 15 18:22:49 GMT 2023 , Edited by admin on Fri Dec 15 18:22:49 GMT 2023
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SMS_ID
100000086969
Created by admin on Fri Dec 15 18:22:49 GMT 2023 , Edited by admin on Fri Dec 15 18:22:49 GMT 2023
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MERCK INDEX
m5385
Created by admin on Fri Dec 15 18:22:49 GMT 2023 , Edited by admin on Fri Dec 15 18:22:49 GMT 2023
PRIMARY Merck Index