Identification

Generic Name
Amperozide
DrugBank Accession Number
DB08927
Background

Amperozide is a diphenylbutylpiperazine atypical antipsychotic which antagonizes 5-HT2A receptors. It inhibits dopamine release and alters the firing of dopaminergic neurons. Investigations regarding the use of the agent revolved primarily around its capability for treating schizophrenia in humans even though the drug was ultimately never clinically adopted for this indication. Alternatively, amperozide's main use lies in veterinary medicine, where it is typically employed to minimize aggression and stress in intensively farmed pigs.

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 401.4927
Monoisotopic: 401.227868975
Chemical Formula
C23H29F2N3O
Synonyms
  • Amperozide

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
U5-hydroxytryptamine receptor 2A
antagonist
Humans
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

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Amperozide is combined with 1,2-Benzodiazepine.
AcenocoumarolThe risk or severity of adverse effects can be increased when Amperozide is combined with Acenocoumarol.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Amperozide.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Amperozide.
AclidiniumAmperozide may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
AgomelatineThe risk or severity of adverse effects can be increased when Agomelatine is combined with Amperozide.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Amperozide.
AlimemazineThe risk or severity of adverse effects can be increased when Alimemazine is combined with Amperozide.
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Amperozide.
AlosetronThe risk or severity of adverse effects can be increased when Alosetron is combined with Amperozide.
Interactions
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Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1,4-diazinane / Amine / Aralkylamine / Aromatic heteromonocyclic compound / Aryl fluoride / Aryl halide / Azacycle / Carbonic acid derivative / Carbonyl group / Diphenylmethane
show 19 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
0M2W3TAG39
CAS number
75558-90-6
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

References

General References
  1. Svartengren J, Simonsson P: Receptor binding properties of amperozide. Pharmacol Toxicol. 1990;66 Suppl 1:8-11. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
PubChem Compound
73333
PubChem Substance
175427159
ChemSpider
66062
BindingDB
50311786
ChEBI
92913
ChEMBL
CHEMBL1079935
ZINC
ZINC000004214849
Wikipedia
Amperozide

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
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. [Article]

Drug created at October 08, 2013 20:39 / Updated at February 21, 2021 18:52