Amperozide

Amperozide
Clinical data
ATCvet code	Template:Infobox drug/formatATCvet; Template:Infobox drug/formatATCvet;
Identifiers
	IUPAC name 4-[4,4-bis(4-fluorophenyl)butyl]-N-ethylpiperazine-1-carboxamide;
CAS Number	75558-90-6 ;
PubChem CID	73333;
ChemSpider	66062 ;
UNII	0M2W3TAG39;
ChEMBL	ChEMBL1079935 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C23H29F2N3O
Molar mass	401.493 g/mol
3D model (JSmol)	Interactive image;
	SMILES CCNC(=O)N1CCN(CC1)CCCC(C2=CC=C(C=C2)F)C3=CC=C(C=C3)F;
	InChI 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) ; Key:NNAIYOXJNVGUOM-UHFFFAOYSA-N ;
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Amperozide is an atypical antipsychotic of the diphenylbutylpiperazine class which acts as an antagonist at the 5-HT_2A receptor.^[1] It does not block dopamine receptors as with most antipsychotic drugs,^[2] but does inhibit dopamine release,^[3]^[4] and alters the firing pattern of dopaminergic neurons.^[5] It was investigated for the treatment of schizophrenia in humans,^[6] but never adopted clinically, its main use is instead in veterinary medicine, primarily in intensively farmed pigs, for decreasing aggression and stress and thereby increasing feeding and productivity.^[7]^[8]^[9]

References

↑ Svartengren J, Simonsson P. Receptor binding properties of amperozide. Pharmacology and Toxicology. 1990;66 Suppl 1:8-11. PMID 2154737
↑ Meltzer HY, Zhang Y, Stockmeier CA. Effect of amperozide on rat cortical 5-HT2 and striatal and limbic dopamine D2 receptor occupancy: implications for antipsychotic action. European Journal of Pharmacology. 1992 May 27;216(1):67-71. PMID 1388121
↑ Eriksson E. Amperozide, a putative anti-psychotic drug: uptake inhibition and release of dopamine in vitro in the rat brain. Life Sciences. 1990;47(23):2111-7. PMID 1979998
↑ Yamamoto BK, Meltzer HY. The effect of the atypical antipsychotic drug, amperozide, on carrier-mediated striatal dopamine release measured in vivo. Journal of Pharmacology and Experimental Therapeutics. 1992 Oct;263(1):180-5. PMID 1403783
↑ Grenhoff J, Tung CS, Ugedo L, Svensson TH. Effects of amperozide, a putative antipsychotic drug, on rat midbrain dopamine neurons recorded in vivo. Pharmacology and Toxicology. 1990;66 Suppl 1:29-33. PMID 2304893
↑ Axelsson R, Nilsson A, Christensson E, Björk A. Effects of amperozide in schizophrenia. An open study of a potent 5-HT2 receptor antagonist. Psychopharmacology (Berlin). 1991;104(3):287-92. PMID 1924636
↑ Kyriakis SC, Martinsson K, Olsson NG, Bjork A. Thin sow syndrome (TSS): the effect of amperozide. British Veterinary Journal. 1990 Sep-Oct;146(5):463-7. PMID 2224491
↑ Kyriakis SC, Olsson NG, Martinsson K, Björk AK. Observations on the action of amperozide: are there social influences on sow-litter productivity? Research in Veterinary Science. 1991 Sep;51(2):169-73. PMID 1788479
↑ Papp I, Waller C, Biro O. Practical experiences in the therapy of postweaning edema disease in piglets. Berliner und Munchener Tierarztliche Wochenschrift. (German) 1996 Oct;109(10):385-7. PMID 8999770

Template:Piperazines

[1] Svartengren J, Simonsson P. Receptor binding properties of amperozide. Pharmacology and Toxicology. 1990;66 Suppl 1:8-11. PMID 2154737

[2] Meltzer HY, Zhang Y, Stockmeier CA. Effect of amperozide on rat cortical 5-HT2 and striatal and limbic dopamine D2 receptor occupancy: implications for antipsychotic action. European Journal of Pharmacology. 1992 May 27;216(1):67-71. PMID 1388121

[3] Eriksson E. Amperozide, a putative anti-psychotic drug: uptake inhibition and release of dopamine in vitro in the rat brain. Life Sciences. 1990;47(23):2111-7. PMID 1979998

[4] Yamamoto BK, Meltzer HY. The effect of the atypical antipsychotic drug, amperozide, on carrier-mediated striatal dopamine release measured in vivo. Journal of Pharmacology and Experimental Therapeutics. 1992 Oct;263(1):180-5. PMID 1403783

[5] Grenhoff J, Tung CS, Ugedo L, Svensson TH. Effects of amperozide, a putative antipsychotic drug, on rat midbrain dopamine neurons recorded in vivo. Pharmacology and Toxicology. 1990;66 Suppl 1:29-33. PMID 2304893

[6] Axelsson R, Nilsson A, Christensson E, Björk A. Effects of amperozide in schizophrenia. An open study of a potent 5-HT2 receptor antagonist. Psychopharmacology (Berlin). 1991;104(3):287-92. PMID 1924636

[7] Kyriakis SC, Martinsson K, Olsson NG, Bjork A. Thin sow syndrome (TSS): the effect of amperozide. British Veterinary Journal. 1990 Sep-Oct;146(5):463-7. PMID 2224491

[8] Kyriakis SC, Olsson NG, Martinsson K, Björk AK. Observations on the action of amperozide: are there social influences on sow-litter productivity? Research in Veterinary Science. 1991 Sep;51(2):169-73. PMID 1788479

[9] Papp I, Waller C, Biro O. Practical experiences in the therapy of postweaning edema disease in piglets. Berliner und Munchener Tierarztliche Wochenschrift. (German) 1996 Oct;109(10):385-7. PMID 8999770

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v t e Antipsychotics (neuroleptics) (N05A)
Typical	Benzamides: Levosulpiride • Nemonapride • Sulpiride • Sultopride • Tiapride • Veralipride; Butyrophenones: Azaperone • Benperidol • Bromperidol • Droperidol • Fluanisone • Haloperidol • Lenperone • Moperone • Pipamperone • Spiperone • Timiperone • Trifluperidol; Diphenylbutylpiperidines: Clopimozide • Fluspirilene • Penfluridol • Pimozide; Phenothiazines: Acepromazine • Acetophenazine • Butaperazine • Carphenazine • Chloracizine • Chlorproethazine • Chlorpromazine • Cyamemazine • Dixyrazine • Fluacizine • Fluphenazine • Levomepromazine/Methotrimeprazine • Mesoridazine • Perazine • Periciazine • Perphenazine • Piperacetazine • Pipotiazine • Prochlorperazine • Promazine • Promethazine • Propiomazine • Sulforidazine • Thiethylperazine • Thiopropazate • Thioproperazine • Thioridazine • Trifluoperazine • Triflupromazine; Thioxanthenes: Chlorprothixene • Clopenthixol • Flupentixol • Thiothixene • Zuclopenthixol; Tricyclics: Amoxapine • Butaclamol • Fluotracen • Loxapine • Metitepine/Methiothepin • Octoclothiepin • Trimipramine; Others: Prothipendyl
Atypical	Benzamides: Amisulpride • Remoxipride; Butyrophenones: Cinuperone • Setoperone; Benzo(iso)oxazole piperidines: Iloperidone • Ocaperidone • Paliperidone • Risperidone; Benzo(iso)thiazole piperazines: Lurasidone • Perospirone • Revospirone • Tiospirone • Ziprasidone; Diphenylbutylpiperazines: Amperozide; Phenylpiperazines: Aripiprazole • Bifeprunox • Elopiprazole • Umespirone; Tricyclics: Asenapine • Carpipramine • Clocapramine • Clotiapine • Clozapine • Fluperlapine • Gevotroline • Metitepine/Methiothepin • Mosapramine • NDMC • Olanzapine • Piquindone • Quetiapine • Tenilapine • Zotepine; Others: Blonanserin • Cariprazine • Molindone • Pimavanserin • Roxindole • Sarizotan • Sertindole • Spiramide
Others	Azacyclonol • Cannabidiol • D-Cycloserine • Lithium • Mifepristone • Oxypertine • Reserpine • Rimcazole • Secretin • Talnetant • Tetrabenazine • Vabicaserin
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III Template:Psychology navs

Amperozide

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References

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Clinical data

ATCvet code	Template:Infobox drug/formatATCvet Template:Infobox drug/formatATCvet
Identifiers
IUPAC name 4-[4,4-bis(4-fluorophenyl)butyl]-N-ethylpiperazine-1-carboxamide
CAS Number	75558-90-6^Y
PubChem CID	73333
ChemSpider	66062^Y
UNII	0M2W3TAG39
ChEMBL	ChEMBL1079935^Y
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C₂₃H₂₉F₂N₃O
Molar mass	401.493 g/mol
3D model (JSmol)	Interactive image
SMILES CCNC(=O)N1CCN(CC1)CCCC(C2=CC=C(C=C2)F)C3=CC=C(C=C3)F
InChI 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)^Y Key:NNAIYOXJNVGUOM-UHFFFAOYSA-N^Y
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