AMPEROZIDE

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

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 231 Target ID: CHEMBL224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2154737	Antagonist 2778		16.5 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 298 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1924636	Primary		Not Provided 504	Unknown Approved Use Unknown
Cocaine addiction 28 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8255902	Primary		Not Provided 504	Unknown Approved Use Unknown

PubMed

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

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.

Name

Type

Language

AMPEROZIDE

Official Name

English

AMPEROZIDE [MI]

Common 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