Melperone (Bunil (PT), Buronil (AT, BE, CZ, DK, FL†, NL†, NO†, SE), Eunerpan (DE))[3] 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.[4]
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Trade names | Buronil |
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Routes of administration | Oral, intramuscular injection |
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Bioavailability | 87% (IM), 54% (Oral via syrup), 65% (Oral, tablet)[1] |
Protein binding | 50% |
Metabolism | Hepatic |
Elimination half-life | 3–4 hours (oral)[1] 6 hours (IM) |
Excretion | Renal (70% as metabolites, 5.5–10.4% as unchanged drug)[1][2] |
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ECHA InfoCard | 100.107.027 |
Chemical and physical data | |
Formula | C16H22FNO |
Molar mass | 263.356 g·mol−1 |
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It has been tried in treatment-resistant cases of schizophrenia with some (albeit limited) success.[4][5][6][7] It has also been reported effective in the treatment of L-DOPA and other forms of psychosis in Parkinson's disease[8] (although a multicentre, double-blind, placebo-controlled study conducted in 2012 failed to support these findings[9]). It is also known to possess anxiolytic properties.[10] It is marketed in the following countries:[3][11]
Melperone is reported to produce significantly less weight gain than clozapine and approximately as much weight gain as typical antipsychotics.[12] It is also purported to produce around as much prolactin secretion as clozapine (which is virtually nil).[13] It is also purported to produce sedative effects[14] and QT interval prolongation.[15] It is also known to produce less extrapyramidal side effects than the first-generation (typical) antipsychotic, thiothixene.[16] It can also produce (usually relatively mild) dry mouth.[17]
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.[23]
Receptor | Ki [nM][24] |
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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 |
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).
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