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
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
| 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.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
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| Effects of amperozide in schizophrenia. An open study of a potent 5-HT2 receptor antagonist. | 1991 |
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| Observations on the action of amperozide: are there social influences on sow-litter productivity? | 1991 Sep |
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| Effect of amperozide on rat cortical 5-HT2 and striatal and limbic dopamine D2 receptor occupancy: implications for antipsychotic action. | 1992 May 27 |
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| The effect of the atypical antipsychotic drug, amperozide, on carrier-mediated striatal dopamine release measured in vivo. | 1992 Oct |
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| Differential effects of classical and newer antipsychotics on the hypermotility induced by two dose levels of D-amphetamine. | 1995 Sep 5 |
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| [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 |
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| 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
Sample Use Guides
in schizophrenia: the maximum daily dose of amperozide was 20 mg
Route of Administration:
Oral
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
Edited
Fri Dec 15 15:34:40 GMT 2023
by
admin
on
Fri Dec 15 15:34:40 GMT 2023
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| Record UNII |
8V2171U69N
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| Record Status |
Validated (UNII)
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| Record Version |
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C66885
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DTXSID501019079
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8V2171U69N
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73334
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m1847
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75529-73-6
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C77259
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300000029418
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C049058
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86725-37-3
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