Identification

Name
Amperozide
Accession Number
DB08927
Type
Small Molecule
Groups
Experimental
Description

Amperozide is an atypical antipsychotic of the diphenylbutylpiperazine class which acts as an antagonist at the 5-HT2A receptor. It does not block dopamine receptors as with most antipsychotic drugs, but does inhibit dopamine release, and alters the firing pattern of dopaminergic neurons. It was investigated for the treatment of schizophrenia in humans, 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. [Wikipedia]

Structure
Thumb
Synonyms
Not Available
Categories
UNII
0M2W3TAG39
CAS number
75558-90-6
Weight
Average: 401.4927
Monoisotopic: 401.227868975
Chemical Formula
C23H29F2N3O
InChI Key
NNAIYOXJNVGUOM-UHFFFAOYSA-N
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)
IUPAC Name
4-[4,4-bis(4-fluorophenyl)butyl]-N-ethylpiperazine-1-carboxamide
SMILES
[H]N(CC)C(=O)N1CCN(CCCC(C2=CC=C(F)C=C2)C2=CC=C(F)C=C2)CC1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U5-hydroxytryptamine receptor 2A
antagonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of adverse effects can be increased when Amperozide is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of adverse effects can be increased when Amperozide is combined with (S)-Warfarin.
2,5-Dimethoxy-4-ethylamphetamineAmperozide may decrease the stimulatory activities of 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Amperozide is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineAmperozide may decrease the stimulatory activities of 3,4-Methylenedioxyamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Amperozide.
4-hydroxycoumarinThe risk or severity of adverse effects can be increased when Amperozide is combined with 4-hydroxycoumarin.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Amperozide.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Amperozide is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when 7-Nitroindazole is combined with Amperozide.
Food Interactions
Not Available

References

General References
  1. Svartengren J, Simonsson P: Receptor binding properties of amperozide. Pharmacol Toxicol. 1990;66 Suppl 1:8-11. [PubMed: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. Eur J Pharmacol. 1992 May 27;216(1):67-71. [PubMed:1388121]
  3. Eriksson E: Amperozide, a putative anti-psychotic drug: uptake inhibition and release of dopamine in vitro in the rat brain. Life Sci. 1990;47(23):2111-7. [PubMed:1979998]
  4. Yamamoto BK, Meltzer HY: The effect of the atypical antipsychotic drug, amperozide, on carrier-mediated striatal dopamine release measured in vivo. J Pharmacol Exp Ther. 1992 Oct;263(1):180-5. [PubMed: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. Pharmacol Toxicol. 1990;66 Suppl 1:29-33. [PubMed:2304893]
  6. Axelsson R, Nilsson A, Christensson E, Bjork A: Effects of amperozide in schizophrenia. An open study of a potent 5-HT2 receptor antagonist. Psychopharmacology (Berl). 1991;104(3):287-92. [PubMed:1924636]
  7. Kyriakis SC, Martinsson K, Olsson NG, Bjork A: Thin sow syndrome (TSS): the effect of amperozide. Br Vet J. 1990 Sep-Oct;146(5):463-7. [PubMed:2224491]
  8. Kyriakis SC, Olsson NG, Martinsson K, Bjork AK: Observations on the action of amperozide: are there social influences on sow-litter productivity? Res Vet Sci. 1991 Sep;51(2):169-73. [PubMed:1788479]
  9. Papp I, Waller C, Biro O: [Practical experiences in the therapy of postweaning edema disease in piglets]. Berl Munch Tierarztl Wochenschr. 1996 Oct;109(10):385-7. [PubMed:8999770]
External Links
PubChem Compound
73333
PubChem Substance
175427159
ChemSpider
66062
BindingDB
50311786
ChEBI
92913
ChEMBL
CHEMBL1079935
Wikipedia
Amperozide

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
logP4.12ChemAxon
pKa (Strongest Acidic)15.61ChemAxon
pKa (Strongest Basic)7.56ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area35.58 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity112.28 m3·mol-1ChemAxon
Polarizability43.52 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Diphenylmethanes
Direct Parent
Diphenylmethanes
Alternative Parents
Phenylbutylamines / Piperazine carboxamides / N-alkylpiperazines / Fluorobenzenes / Aralkylamines / Aryl fluorides / Ureas / Trialkylamines / Azacyclic compounds / Organopnictogen compounds
show 4 more
Substituents
Diphenylmethane / Phenylbutylamine / Piperazine-1-carboxamide / Fluorobenzene / Halobenzene / N-alkylpiperazine / Aralkylamine / Aryl halide / 1,4-diazinane / Piperazine
show 19 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Virus receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...
Gene Name
HTR2A
Uniprot ID
P28223
Uniprot Name
5-hydroxytryptamine receptor 2A
Molecular Weight
52602.58 Da
References
  1. Svartengren J, Simonsson P: Receptor binding properties of amperozide. Pharmacol Toxicol. 1990;66 Suppl 1:8-11. [PubMed:2154737]

Drug created on October 08, 2013 14:39 / Updated on November 02, 2018 06:56