Melperone

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| _other_data=1-(4-fluorophenyl)-4-(4-methylpiperidin-1-yl)butan-1-one

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Melperone (Bunil (PT), Buronil (AT, BE, CZ, DK, FI†, NL†, NO†, SE), Eunerpan (DE))[1] 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.[2]

Marketing and indications

It has been tried in treatment-resistant cases of schizophrenia with some (albeit limited) success.[2][3][4][5] It has also been reported effective in the treatment of L-DOPA and other forms of psychosis in Parkinson's disease[6] (although a multicentre, double-blind, placebo-controlled study conducted in 2012 failed to support these findings[7]). It is also known to possess anxiolytic properties.[8] It is marketed in the following countries:[1][9]

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Adverse effects

Melperone is reported to produce significantly less weight gain than clozapine and approximately as much weight gain as typical antipsychotics.[10] It is also purported to produce around as much prolactin secretion as clozapine (which is virtually nil).[11] It is also purported to produce sedative effects[12] and QT interval prolongation.[13] It is also known to produce less extrapyramidal side effects than the first-generation (typical) antipsychotic, thiothixene.[14] It can also produce (usually relatively mild) dry mouth.[15]

Other common adverse effects include[16][17][18]

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Rare adverse effects include[16][17][18]
Unknown frequency adverse effects include[16][17][18]

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  • 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.[19][20][21]

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.[22]

Receptor Ki [nM][23]
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

File:Melperone synthesis.svg
Thieme Patents:[24][25] 86%:[26]

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

References

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  1. ↑ a b Script error: No such module "citation/CS1".
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  5. ↑ Script error: No such module "Citation/CS1".
  6. ↑ Barbato L, Monge A, Stocchi F, Nordera G. Melperone in the treatment of iatrogenic psychosis in Parkinson’s disease. Funct Neurol. 1996 Aug;11(4):201–7.
  7. ↑ Script error: No such module "Citation/CS1".
  8. ↑ Script error: No such module "Citation/CS1".
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  14. ↑ Script error: No such module "Citation/CS1".
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  22. ↑ Script error: No such module "Citation/CS1".
  23. ↑ Script error: No such module "citation/CS1".
  24. ↑ J Lassen, S Hernestam, N Sterner, U.S. patent 3816433 (1974 to Ferrosan Ab).
  25. ↑ BE651144 idem Erik Harry Hernestam Sven, et al.<templatestyles src="Citation/styles.css"/>Template:Citation/make link Script error: No such module "Check for unknown parameters". (1966 to Ferrosan); CA, 63, 13244c
  26. ↑ Leyva-Pérez, Antonio; Cabrero-Antonino, Jose R.; Rubio-Marqués, Paula; Al-Resayes, Saud I.; Corma, Avelino (2014). "Synthesis of the ortho/meta/para Isomers of Relevant Pharmaceutical Compounds by Coupling a Sonogashira Reaction with a Regioselective Hydration". ACS Catalysis. 4 (3): 722–731. doi:10.1021/cs401075z.

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External links

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