Amperozide
Star2
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
- Weight
- Average: 401.4927
Monoisotopic: 401.227868975 - Chemical Formula
- C23H29F2N3O
- Synonyms
- Amperozide
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism U5-hydroxytryptamine receptor 2A antagonistHumans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Amperozide is combined with 1,2-Benzodiazepine. Acenocoumarol The risk or severity of adverse effects can be increased when Amperozide is combined with Acenocoumarol. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Amperozide. Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with Amperozide. Agomelatine The risk or severity of CNS depression can be increased when Agomelatine is combined with Amperozide. - Food Interactions
- Not Available
Categories
- Drug Categories
- Antidepressive Agents
- Antipsychotic Agents
- Central Nervous System Agents
- Central Nervous System Depressants
- Neurotoxic agents
- Neurotransmitter Agents
- Psychotropic Drugs
- Serotonin 5-HT2 Receptor Antagonists
- Serotonin 5-HT2A Receptor Antagonists
- Serotonin Agents
- Serotonin Receptor Antagonists
- Tranquilizing Agents
- 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
- Svartengren J, Simonsson P: Receptor binding properties of amperozide. Pharmacol Toxicol. 1990;66 Suppl 1:8-11. [Article]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- External Links
- PubChem Compound
- 73333
- PubChem Substance
- 175427159
- ChemSpider
- 66062
- BindingDB
- 50311786
- ChEBI
- 92913
- ChEMBL
- CHEMBL1079935
- ZINC
- ZINC000004214849
- Wikipedia
- Amperozide
Clinical Trials
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
Property Value Source Water Solubility 0.0131 mg/mL ALOGPS logP 4.15 ALOGPS logP 4.12 Chemaxon logS -4.5 ALOGPS pKa (Strongest Acidic) 15.61 Chemaxon pKa (Strongest Basic) 7.56 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 35.58 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 112.28 m3·mol-1 Chemaxon Polarizability 43.52 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0udi-0001900000-3f1a59e04264501216d1 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0ue9-3009800000-f061f1622ccd8fd9c21f Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-0009100000-f19fc9e8b5e40b34b860 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0zfs-0049600000-c66356332f2903f47559 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0nmr-0189100000-954a0e9513eecb7d858a Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0w3a-1397100000-befbf972e144c95d02c6 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 195.89323 predictedDeepCCS 1.0 (2019) [M+H]+ 198.26357 predictedDeepCCS 1.0 (2019) [M+Na]+ 205.42473 predictedDeepCCS 1.0 (2019)
Targets
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1. Details5-hydroxytryptamine receptor 2A
- 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
- 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