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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 of AMPEROZIDE HYDROCHLORIDE

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

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

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
16.5 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

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

Patents

Sample Use Guides

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 Fri Dec 15 15:34:40 GMT 2023
Edited
by admin
on Fri Dec 15 15:34:40 GMT 2023
Record UNII
8V2171U69N
Record Status Validated (UNII)
Record Version
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Name Type Language
AMPEROZIDE HYDROCHLORIDE
MI  
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
Created by admin on Fri Dec 15 15:34:40 GMT 2023 , Edited by admin on Fri Dec 15 15:34:40 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID501019079
Created by admin on Fri Dec 15 15:34:40 GMT 2023 , Edited by admin on Fri Dec 15 15:34:40 GMT 2023
PRIMARY
FDA UNII
8V2171U69N
Created by admin on Fri Dec 15 15:34:40 GMT 2023 , Edited by admin on Fri Dec 15 15:34:40 GMT 2023
PRIMARY
PUBCHEM
73334
Created by admin on Fri Dec 15 15:34:40 GMT 2023 , Edited by admin on Fri Dec 15 15:34:40 GMT 2023
PRIMARY
MERCK INDEX
m1847
Created by admin on Fri Dec 15 15:34:40 GMT 2023 , Edited by admin on Fri Dec 15 15:34:40 GMT 2023
PRIMARY Merck Index
CAS
75529-73-6
Created by admin on Fri Dec 15 15:34:40 GMT 2023 , Edited by admin on Fri Dec 15 15:34:40 GMT 2023
ALTERNATIVE
NCI_THESAURUS
C77259
Created by admin on Fri Dec 15 15:34:40 GMT 2023 , Edited by admin on Fri Dec 15 15:34:40 GMT 2023
PRIMARY
SMS_ID
300000029418
Created by admin on Fri Dec 15 15:34:40 GMT 2023 , Edited by admin on Fri Dec 15 15:34:40 GMT 2023
PRIMARY
MESH
C049058
Created by admin on Fri Dec 15 15:34:40 GMT 2023 , Edited by admin on Fri Dec 15 15:34:40 GMT 2023
PRIMARY
CAS
86725-37-3
Created by admin on Fri Dec 15 15:34:40 GMT 2023 , Edited by admin on Fri Dec 15 15:34:40 GMT 2023
PRIMARY
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