AMPEROZIDE HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H29F2N3O.ClH
Molecular Weight	437.954
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=OEQHKNWFXHBJIT-UHFFFAOYSA-N

InChI=1S/C23H29F2N3O.ClH/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);1H

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
Effect of amperozide on rat cortical 5-HT2 and striatal and limbic dopamine D2 receptor occupancy: implications for antipsychotic action.	1992 May 27	1388121
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
Unbiased descriptor and parameter selection confirms the potential of proteochemometric modelling.	2005 Mar 10	15760465
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

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 HYDROCHLORIDE

Common Name

English

AMPEROZIDE HYDROCHLORIDE [MI]

Common Name

English

AMPEROZIDE HCL

Common Name

English

HOGPAX

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66885