Melperone
Identification
- Summary
Melperone is an atypical butyrophenone antipsychotic used to treat sleep disorders, confusion, and psychomotor dysfunction associated with geriatric, psychiatric, and alcohol-dependent patients.
- Generic Name
- Melperone
- DrugBank Accession Number
- DB09224
- Background
Melperone is an atypical antipsychotic of the butyrophenone chemical class, making it structurally related to the typical antipsychotic haloperidol. Melperone has been used for a span of greater than 30 years in the European Union 5. It has been well established in the treatment of confusion, anxiety, restlessness (particularly in the elderly) and schizophrenia as It is known to be well-tolerated with an excellent safety profile. Recently, it has been studied as a treatment of psychosis related to Parkinson's disease 5.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Melperone (DB09224)
- Weight
- Average: 263.356
Monoisotopic: 263.168542495 - Chemical Formula
- C16H22FNO
- Synonyms
- Melperone
- External IDs
- FG 5111
- FG-5111
Pharmacology
- Indication
For the treatment of schizophrenia, sleep, disorders, agitation and mentally confused states 6,8,10.
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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Melperone has been demonstrated to produce an antipsychotic effect at doses that cause minimal extrapyramidal symptoms frequently associated with more traditional antipsychotics 6,8.
- Mechanism of action
Melperone demonstrates antagonist activity at D2 dopaminergic and 5HT2A serotonergic receptors 8. It has a weak affinity to D2 receptors and possesses less risk of inducing dopamine receptor supersensitivity after both acute and chronic administration [L3146]. In addition, the ratio of dopamine D4/D2 occupancy for melperone has been shown to resemble the binding profile of clozapine 9.
Target Actions Organism ADopamine D2 receptor antagonistHumans - Absorption
Oral doses are rapidly absorbed (Tmax 1.5–3.0 hours post oral ingestion)[A3145].
- Volume of distribution
Not Available
- Protein binding
Melperone has a bioavailability of 50-70% [A3145].
- Metabolism
Mainly hepatic 11.
- Route of elimination
Excreted mainly in the urine, with small amounts of unchanged drug 11.
- Half-life
Approximately 3-4 hours after oral administration 1. After intramuscular injection, the half-life has been found to be approximately 6 hours 1.
- Clearance
Not Available
- Adverse Effects
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An overdose of Melperone may result in cardiac arrhythmias 4.
- 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 adverse effects can be increased when Melperone is combined with 1,2-Benzodiazepine. Abacavir Abacavir may decrease the excretion rate of Melperone which could result in a higher serum level. Acebutolol Acebutolol may increase the arrhythmogenic activities of Melperone. Aceclofenac Aceclofenac may decrease the excretion rate of Melperone which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Melperone which could result in a higher serum level. Acetaminophen The metabolism of Acetaminophen can be decreased when combined with Melperone. Acetazolamide The risk or severity of adverse effects can be increased when Acetazolamide is combined with Melperone. Acetophenazine The risk or severity of adverse effects can be increased when Acetophenazine is combined with Melperone. Acetyldigitoxin Acetyldigitoxin may increase the arrhythmogenic activities of Melperone. Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Melperone which could result in a higher serum level. 
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- Not Available
Products
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Ingredient UNII CAS InChI Key Melperone hydrochloride 88G640374K 1622-79-3 Not applicable - International/Other Brands
- Bunil
Categories
- ATC Codes
- N05AD03 — Melperone
- Drug Categories
- Antiarrhythmic agents
- Antipsychotic Agents
- Antipsychotic Agents (Second Generation [Atypical])
- Butyrophenone Derivatives
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Dopamine Antagonists
- Dopamine D2 Receptor Antagonists
- Drugs that are Mainly Renally Excreted
- Ketones
- Moderate Risk QTc-Prolonging Agents
- Nervous System
- Neurotoxic agents
- Psycholeptics
- Psychotropic Drugs
- QTc Prolonging Agents
- Tranquilizing Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Carbonyl compounds
- Direct Parent
- Alkyl-phenylketones
- Alternative Parents
- Phenylbutylamines / Butyrophenones / Benzoyl derivatives / Aryl alkyl ketones / Fluorobenzenes / Piperidines / Gamma-amino ketones / Aryl fluorides / Trialkylamines / Azacyclic compounds show 4 more
- Substituents
- Alkyl-phenylketone / Amine / Aromatic heteromonocyclic compound / Aryl alkyl ketone / Aryl fluoride / Aryl halide / Azacycle / Benzenoid / Benzoyl / Butyrophenone show 16 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- J8WA3K39B7
- CAS number
- 3575-80-2
- InChI Key
- DKMFBWQBDIGMHM-UHFFFAOYSA-N
- InChI
- InChI=1S/C16H22FNO/c1-13-8-11-18(12-9-13)10-2-3-16(19)14-4-6-15(17)7-5-14/h4-7,13H,2-3,8-12H2,1H3
- IUPAC Name
- 1-(4-fluorophenyl)-4-(4-methylpiperidin-1-yl)butan-1-one
- SMILES
- CC1CCN(CCCC(=O)C2=CC=C(F)C=C2)CC1
References
- General References
- Borgstrom L, Larsson H, Molander L: Pharmacokinetics of parenteral and oral melperone in man. Eur J Clin Pharmacol. 1982;23(2):173-6. [Article]
- Sumiyoshi T, Jayathilake K, Meltzer HY: A comparison of two doses of melperone, an atypical antipsychotic drug, in the treatment of schizophrenia. Schizophr Res. 2003 Jul 1;62(1-2):65-72. [Article]
- Hui WK, Mitchell LB, Kavanagh KM, Gillis AM, Wyse DG, Manyari DE, Duff HJ: Melperone: electrophysiologic and antiarrhythmic activity in humans. J Cardiovasc Pharmacol. 1990 Jan;15(1):144-9. [Article]
- Koppel, J et al. (1988). Gas chromatographic- mass spectrometric study of urinary metabolism of melperone. Journal of Biomedical Chromatography.
- Melperone (an Anti-Psychotic) in Patients With Psychosis Associated With Parkinson's Disease [Link]
- The effect of melperone, an atypical antipsychotic drug, on cognitive function in schizophrenia [Link]
- Melperone MSDS [Link]
- Melperone in Treatment-Refractory Schizophrenia: A Case Series [Link]
- Melperone in Treatment-Refractory Schizophrenia: A Case Series [Link]
- Melperone [Link]
- Quantification of selected antidepressants and antipsychotics in clinical samples using chromatographic methods combined with mass spectrometry: A review (2006-2015) [Link]
- Pharmacological data of the atypical neuroleptic compound melperone (Buronil) [Link]
- Development of orally disintegrating tablets comprising controlled-release multiparticulate beads [Link]
- External Links
- KEGG Drug
- D07309
- PubChem Compound
- 15387
- PubChem Substance
- 310265130
- ChemSpider
- 14646
- BindingDB
- 81771
- 29961
- ChEBI
- 93626
- ChEMBL
- CHEMBL1531134
- ZINC
- ZINC000000001672
- Wikipedia
- Melperone
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Terminated Treatment Anxiety Disorders / Dementia / Depression / Psychosomatic Disorders / Schizophrenia 1 2 Completed Treatment Parkinson's Disease (PD) / Psychosis 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, film coated Oral Solution Oral 25 MG/5ML Tablet, film coated Oral 50 MG Tablet, film coated Oral 100 MG Tablet, film coated Oral 10 MG Tablet, film coated Oral 25 MG Solution Oral 25 mg/mL - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 78-82 [L1318] boiling point (°C) 120-125 [L1318] - Predicted Properties
Property Value Source Water Solubility 0.049 mg/mL ALOGPS logP 3.89 ALOGPS logP 3.23 ChemAxon logS -3.7 ALOGPS pKa (Strongest Acidic) 16.4 ChemAxon pKa (Strongest Basic) 8.9 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 20.31 Å2 ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 76.25 m3·mol-1 ChemAxon Polarizability 30.25 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No 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 Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-02t9-1970000000-6679994e650d6735e617 LC-MS/MS Spectrum - LC-ESI-QFT , positive LC-MS/MS splash10-0300-0940000000-5f2b3e89368f333f4076
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Potassium channel regulator activity
- Specific Function
- Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
- Gene Name
- DRD2
- Uniprot ID
- P14416
- Uniprot Name
- D(2) dopamine receptor
- Molecular Weight
- 50618.91 Da
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Grozinger M, Dragicevic A, Hiemke C, Shams M, Muller MJ, Hartter S: Melperone is an inhibitor of the CYP2D6 catalyzed O-demethylation of venlafaxine. Pharmacopsychiatry. 2003 Jan;36(1):3-6. doi: 10.1055/s-2003-38084. [Article]
Drug created on October 22, 2015 20:15 / Updated on May 05, 2021 20:31