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
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)
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 |
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 |
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Target ID: CHEMBL224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2154737 |
16.5 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Effects of amperozide, a putative antipsychotic drug, on rat midbrain dopamine neurons recorded in vivo. | 1990 |
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Receptor binding properties of amperozide. | 1990 |
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[Practical experiences in the therapy of postweaning edema disease in piglets]. | 1996 Oct |
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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 |
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Modulation of high alcohol drinking in the inbred Fawn-Hooded (FH/Wjd) rat strain: implications for treatment. | 2006 Sep |
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Mining biologically-active molecules for inhibitors of fatty acid amide hydrolase (FAAH): identification of phenmedipham and amperozide as FAAH inhibitors. | 2009 Dec 1 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1924636
in schizophrenia: the maximum daily dose of amperozide was 20 mg
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1979998
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
Sat Dec 16 16:31:44 UTC 2023
by
admin
on
Sat Dec 16 16:31:44 UTC 2023
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Record UNII |
0M2W3TAG39
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Record Status |
Validated (UNII)
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Record Version |
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WHO-VATC |
QN05AX90
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NCI_THESAURUS |
C28197
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NCI_THESAURUS |
C29756
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DB08927
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100000086913
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193
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m1847
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Amperozide
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DTXSID6048416
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CHEMBL1079935
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C74191
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73333
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C049058
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SUB05483MIG
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75558-90-6
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0M2W3TAG39
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |