NAV

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
3D
Similar Structures
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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Associated Conditions
Contraindications & Blackbox Warnings
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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 12. In addition, the ratio of dopamine D4/D2 occupancy for melperone has been shown to resemble the binding profile of clozapine 9.

TargetActionsOrganism
ADopamine D2 receptor
antagonist
Humans
Absorption

Oral doses are rapidly absorbed (Tmax 1.5–3.0 hours post oral ingestion)13.

Volume of distribution

Not Available

Protein binding

Melperone has a bioavailability of 50-70% 13.

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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Toxicity

An overdose of Melperone may result in cardiac arrhythmias 4,1.

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
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1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Melperone is combined with 1,2-Benzodiazepine.
AbacavirAbacavir may decrease the excretion rate of Melperone which could result in a higher serum level.
AcebutololAcebutolol may increase the arrhythmogenic activities of Melperone.
AceclofenacAceclofenac may decrease the excretion rate of Melperone which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Melperone which could result in a higher serum level.
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Melperone.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Melperone.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Melperone.
AcetyldigitoxinAcetyldigitoxin may increase the arrhythmogenic activities of Melperone.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Melperone which could result in a higher serum level.
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Melperone hydrochloride88G640374K1622-79-3Not applicable
International/Other Brands
Bunil

Categories

ATC Codes
N05AD03 — Melperone
Drug Categories
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
  1. Borgstrom L, Larsson H, Molander L: Pharmacokinetics of parenteral and oral melperone in man. Eur J Clin Pharmacol. 1982;23(2):173-6. [Article]
  2. 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]
  3. 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]
  4. Koppel, J et al. (1988). Gas chromatographic- mass spectrometric study of urinary metabolism of melperone. Journal of Biomedical Chromatography.
  5. Melperone (an Anti-Psychotic) in Patients With Psychosis Associated With Parkinson's Disease [Link]
  6. The effect of melperone, an atypical antipsychotic drug, on cognitive function in schizophrenia [Link]
  7. Melperone MSDS [Link]
  8. Melperone in Treatment-Refractory Schizophrenia: A Case Series [Link]
  9. Melperone in Treatment-Refractory Schizophrenia: A Case Series [Link]
  10. Melperone [Link]
  11. Quantification of selected antidepressants and antipsychotics in clinical samples using chromatographic methods combined with mass spectrometry: A review (2006-2015) [Link]
  12. Pharmacological data of the atypical neuroleptic compound melperone (Buronil) [Link]
  13. Development of orally disintegrating tablets comprising controlled-release multiparticulate beads [Link]
KEGG Drug
D07309
PubChem Compound
15387
PubChem Substance
310265130
ChemSpider
14646
BindingDB
81771
RxNav
29961
ChEBI
93626
ChEMBL
CHEMBL1531134
ZINC
ZINC000000001672
Wikipedia
Melperone

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3TerminatedTreatmentAnxiety Disorders / Dementia / Depression / Psychosomatic Disorders / Schizophrenia1
2CompletedTreatmentParkinson's Disease (PD) / Psychosis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, film coatedOral25 mg
Tablet, film coatedOral50 mg
SolutionOral25 MG/5ML
Tablet, film coatedOral100 MG
Tablet, film coatedOral10 MG
SolutionOral25 mg/mL
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)78-82[L1318]
boiling point (°C)120-125[L1318]
Predicted Properties
PropertyValueSource
Water Solubility0.049 mg/mLALOGPS
logP3.89ALOGPS
logP3.23Chemaxon
logS-3.7ALOGPS
pKa (Strongest Acidic)16.4Chemaxon
pKa (Strongest Basic)8.9Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area20.31 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity76.25 m3·mol-1Chemaxon
Polarizability30.25 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
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
MS/MS Spectrum - , positiveLC-MS/MSsplash10-02t9-1970000000-6679994e650d6735e617
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0300-0940000000-5f2b3e89368f333f4076

Targets

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Details1. Dopamine D2 receptor
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

Details1. Cytochrome P450 2D6
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
  1. 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 at October 22, 2015 20:15 / Updated at February 03, 2022 21:01