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)
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 |
---|---|---|---|
Target ID: CHEMBL224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2154737 |
16.5 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
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 |
|
Thin sow syndrome (TSS): the effect of amperozide. | 1990 Sep-Oct |
|
Observations on the action of amperozide: are there social influences on sow-litter productivity? | 1991 Sep |
|
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 |
|
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 Sep |
|
Mining biologically-active molecules for inhibitors of fatty acid amide hydrolase (FAAH): identification of phenmedipham and amperozide as FAAH inhibitors. | 2009 Dec 1 |
|
Brain Activation by Peptide Pro-Leu-Gly-NH(2) (MIF-1). | 2010 |
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.
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
WHO-VATC |
QN05AX90
Created by
admin on Sat Dec 16 16:31:44 GMT 2023 , Edited by admin on Sat Dec 16 16:31:44 GMT 2023
|
||
|
NCI_THESAURUS |
C28197
Created by
admin on Sat Dec 16 16:31:44 GMT 2023 , Edited by admin on Sat Dec 16 16:31:44 GMT 2023
|
||
|
NCI_THESAURUS |
C29756
Created by
admin on Sat Dec 16 16:31:44 GMT 2023 , Edited by admin on Sat Dec 16 16:31:44 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
DB08927
Created by
admin on Sat Dec 16 16:31:44 GMT 2023 , Edited by admin on Sat Dec 16 16:31:44 GMT 2023
|
PRIMARY | |||
|
5033
Created by
admin on Sat Dec 16 16:31:44 GMT 2023 , Edited by admin on Sat Dec 16 16:31:44 GMT 2023
|
PRIMARY | |||
|
100000086913
Created by
admin on Sat Dec 16 16:31:44 GMT 2023 , Edited by admin on Sat Dec 16 16:31:44 GMT 2023
|
PRIMARY | |||
|
193
Created by
admin on Sat Dec 16 16:31:44 GMT 2023 , Edited by admin on Sat Dec 16 16:31:44 GMT 2023
|
PRIMARY | |||
|
m1847
Created by
admin on Sat Dec 16 16:31:44 GMT 2023 , Edited by admin on Sat Dec 16 16:31:44 GMT 2023
|
PRIMARY | Merck Index | ||
|
Amperozide
Created by
admin on Sat Dec 16 16:31:44 GMT 2023 , Edited by admin on Sat Dec 16 16:31:44 GMT 2023
|
PRIMARY | |||
|
DTXSID6048416
Created by
admin on Sat Dec 16 16:31:44 GMT 2023 , Edited by admin on Sat Dec 16 16:31:44 GMT 2023
|
PRIMARY | |||
|
CHEMBL1079935
Created by
admin on Sat Dec 16 16:31:44 GMT 2023 , Edited by admin on Sat Dec 16 16:31:44 GMT 2023
|
PRIMARY | |||
|
C74191
Created by
admin on Sat Dec 16 16:31:44 GMT 2023 , Edited by admin on Sat Dec 16 16:31:44 GMT 2023
|
PRIMARY | |||
|
73333
Created by
admin on Sat Dec 16 16:31:44 GMT 2023 , Edited by admin on Sat Dec 16 16:31:44 GMT 2023
|
PRIMARY | |||
|
C049058
Created by
admin on Sat Dec 16 16:31:44 GMT 2023 , Edited by admin on Sat Dec 16 16:31:44 GMT 2023
|
PRIMARY | |||
|
SUB05483MIG
Created by
admin on Sat Dec 16 16:31:44 GMT 2023 , Edited by admin on Sat Dec 16 16:31:44 GMT 2023
|
PRIMARY | |||
|
75558-90-6
Created by
admin on Sat Dec 16 16:31:44 GMT 2023 , Edited by admin on Sat Dec 16 16:31:44 GMT 2023
|
PRIMARY | |||
|
0M2W3TAG39
Created by
admin on Sat Dec 16 16:31:44 GMT 2023 , Edited by admin on Sat Dec 16 16:31:44 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)