AMPEROZIDE

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H29F2N3O
Molecular Weight	401.4927
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCNC(=O)N1CCN(CCCC(C2=CC=C(F)C=C2)C3=CC=C(F)C=C3)CC1

InChI

InChIKey=NNAIYOXJNVGUOM-UHFFFAOYSA-N

InChI=1S/C23H29F2N3O/c1-2-26-23(29)28-16-14-27(15-17-28)13-3-4-22(18-5-9-20(24)10-6-18)19-7-11-21(25)12-8-19/h5-12,22H,2-4,13-17H2,1H3,(H,26,29)

HIDE SMILES / InChI

Molecular Formula	C23H29F2N3O
Molecular Weight	401.4927
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/2154737 | https://www.ncbi.nlm.nih.gov/pubmed/1924636

Amperozide (FG 5606, N-ethyl-4-[4',4'-bis(p-fluorophenyl)butyl]-1-piperazine-carboxamide) is an atypical antipsychotic drug which has relatively weak in vitro affinity for striatal dopamine2 (D2) receptors and a strong affinity for the cortical 5-HT2A receptor. It was shown in animal models, that amperozide could attenuate craving for cocaine. In addition, this drug was studied in patients with schizophrenia and was shown, that several patients had improvements as was assessed by the Clinical Global Improvement Scale. However, these studies were discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 2a (5-HT2a) receptor 237 Target ID: CHEMBL224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2154737	Antagonist 2849		16.5 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 305 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1924636	Primary		Not Provided 511	Unknown Approved Use Unknown
Cocaine addiction 29 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8255902	Primary		Not Provided 511	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Brain Activation by Peptide Pro-Leu-Gly-NH(2) (MIF-1).	2010	20721355
Mining biologically-active molecules for inhibitors of fatty acid amide hydrolase (FAAH): identification of phenmedipham and amperozide as FAAH inhibitors.	2009-12-01	19850474
A new homogeneous high-throughput screening assay for profiling compound activity on the human ether-a-go-go-related gene channel.	2009-11-01	19583963
Behavioral and biochemical effects of amperozide and serotonin agents on nigrostriatal and mesolimbic dopamine systems.	2008-04-30	18666714
Effect of DOV 102,677 on the volitional consumption of ethanol by Myers' high ethanol-preferring rat.	2007-11	17908267
Modulation of high alcohol drinking in the inbred Fawn-Hooded (FH/Wjd) rat strain: implications for treatment.	2006-09	16961764
Adjunctive treatment with mianserin enhances effects of raclopride on cortical dopamine output and, in parallel, its antipsychotic-like effect.	2005-12	18568117
Adjunctive treatment with mianserin enhances effects of raclopride on cortical dopamine output and, in parallel, its antipsychotic-like effect.	2005-09	18568103
Unbiased descriptor and parameter selection confirms the potential of proteochemometric modelling.	2005-03-10	15760465
Effects of cocaine and putative atypical antipsychotics on rat social behavior: an ethopharmacological study.	2002-11	12213521
Acute effects of amperozide and paroxetine on social cohesion in male conspecifics.	2002-06	12127016
Functional alteration by NMDA antagonist: effects of L-Dopa, neuroleptics drug and postnatal administration.	2002	12373526
Inverse agonist actions of typical and atypical antipsychotic drugs at the human 5-hydroxytryptamine(2C) receptor.	2001-10	11561066
[Practical experiences in the therapy of postweaning edema disease in piglets].	1996-10	8999770
Differential effects of classical and newer antipsychotics on the hypermotility induced by two dose levels of D-amphetamine.	1995-09-05	7498321
The effect of the atypical antipsychotic drug, amperozide, on carrier-mediated striatal dopamine release measured in vivo.	1992-10	1403783
Effect of amperozide on rat cortical 5-HT2 and striatal and limbic dopamine D2 receptor occupancy: implications for antipsychotic action.	1992-05-27	1388121
Observations on the action of amperozide: are there social influences on sow-litter productivity?	1991-09	1788479
Effects of amperozide in schizophrenia. An open study of a potent 5-HT2 receptor antagonist.	1991	1924636
Thin sow syndrome (TSS): the effect of amperozide.	1990-09-01	2224491
Effects of amperozide, a putative antipsychotic drug, on rat midbrain dopamine neurons recorded in vivo.	1990	2304893
Receptor binding properties of amperozide.	1990	2154737
Amperozide, a putative anti-psychotic drug: uptake inhibition and release of dopamine in vitro in the rat brain.	1990	1979998

Patents

Sample Use Guides

In Vivo Use Guide

in schizophrenia: the maximum daily dose of amperozide was 20 mg

Route of Administration: Oral

In Vitro Use Guide

The effects of amperozide on the uptake and release of 3H-dopamine in vitro were investigated. Amperozide inhibited the amphetamine-stimulated release of dopamine from perfused rat striatal tissue in a dose-dependent manner. With 1 and 10 microM amperozide, there was significant inhibition of the amphetamine-stimulated release of dopamine, to 44 and 36% of control. In contrast, 10 microM amperozide significantly strengthened the electrically stimulated release of dopamine from perfused striatal slices. Amperozide 1-10 microM had no significant effect on the potassium-stimulated release of dopamine. 10 microM amperozide also slightly increased the basal release of 3H-dopamine from perfused striatal tissue. The uptake of dopamine in striatal tissue was inhibited by amperozide with IC50 values of 18 microM for uptake in chopped tissue and 1.0 microM for uptake in synaptosomes. Amperozide also inhibited the uptake of serotonin in synaptosomes from frontal cortex, IC50 = 0.32 microM and the uptake of noradrenaline in cortical synaptosomes, IC50 = 0.78 microM.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 07:55:35 GMT 2025` Edited by `admin` on `Wed Apr 02 07:55:35 GMT 2025`
Record UNII	0M2W3TAG39
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AMPEROZIDE [MI]

Preferred Name

English

AMPEROZIDE

Official Name

English

4-(4,4-BIS(P-FLUOROPHENYL)BUTYL)-N-ETHYL-1-PIPERAZINECARBOXAMIDE

Common Name

English

amperozide [INN]

Common Name

English

Amperozide [WHO-DD]

Common Name

English

AMPEROZIDE [MART.]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QN05AX90