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Atypical antipsychotic
Melperone
Другие языки:

Melperone

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Melperone
Skeletal formula of melperone
Space-filling model of the melperone molecule
Clinical data
Trade names Buronil
AHFS/Drugs.com International Drug Names
Routes of
administration		 Oral, intramuscular injection
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability 87% (IM), 54% (Oral via syrup), 65% (Oral, tablet)
Protein binding 50%
Metabolism Hepatic
Elimination half-life 3–4 hours (oral)
6 hours (IM)
Excretion Renal (70% as metabolites, 5.5–10.4% as unchanged drug)
Identifiers
  • 1-(4-fluorophenyl)-4-(4-methylpiperidin-1-yl)butan-1-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.107.027
Chemical and physical data
Formula C16H22FNO
Molar mass 263.356 g·mol−1
3D model (JSmol)
  • Fc1ccc(cc1)C(=O)CCCN2CCC(CC2)C
  • 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 checkY
  • Key:DKMFBWQBDIGMHM-UHFFFAOYSA-N checkY
  (verify)

Melperone (Bunil (PT), Buronil (AT, BE, CZ, DK, FL†, NL†, NO†, SE), Eunerpan (DE)) is an atypical antipsychotic of the butyrophenone chemical class, making it structurally related to the typical antipsychotic haloperidol. It first entered clinical use in 1960s.

Marketing and indications

It has been tried in treatment-resistant cases of schizophrenia with some (albeit limited) success. It has also been reported effective in the treatment of L-DOPA and other forms of psychosis in Parkinson's disease (although a multicentre, double-blind, placebo-controlled study conducted in 2012 failed to support these findings). It is also known to possess anxiolytic properties. It is marketed in the following countries:

Adverse effects

Melperone is reported to produce significantly less weight gain than clozapine and approximately as much weight gain as typical antipsychotics. It is also purported to produce around as much prolactin secretion as clozapine (which is virtually nil). It is also purported to produce sedative effects and QT interval prolongation. It is also known to produce less extrapyramidal side effects than the first-generation (typical) antipsychotic, thiothixene. It can also produce (usually relatively mild) dry mouth.

Other common adverse effects include
Rare adverse effects include
Unknown frequency adverse effects include
  • Seizures (probably rare/uncommon)
  • Increased intraocular pressure
  • Intrahepatic cholestasis (probably rare)
  • Orthostatic hypotension (probably common)
  • Arrhythmias
  • Rash
  • Hyperprolactinemia (which can lead to e.g. galactorrhea, gynecomastia)
  • Weight gain
  • Increased appetite

Interactions

Melperone is reported to be a CYP2D6 inhibitor.

Pharmacology

Melperone binds to the dopamine D2 receptor, just like all other clinically-utilized antipsychotics, but it does so with a very low affinity and hence may be liable to rapidly dissociate from the D2 receptor hence potentially giving it the profile of an atypical antipsychotic.

Receptor Ki [nM]
5-HT1A 2,200
5-HT1D 3,400
5-HT2A 230
5-HT2C 2,100
5-HT6 1,254
5-HT7 578
α1 180
α2 150
M1 >10,000
M2 2,400
M3 >10,000
M4 4,400
M5 >10,000
D2 194
D3 347
D4 555
H1 580

Synthesis

Thieme Patents: 86%:

For the last step of the synthesis the sidechain 4-Chloro-4'-Fluorobutyrophenone [3874-54-2] (1) is attached to 4-Methylpiperidine (4-Pipecoline) [626-58-4] (2).

See also

External links


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