Fluperlapine (NB 106-689), also known as fluoroperlapine, is a morphanthridine (11H-dibenzo[b,e]azepine) atypical antipsychotic with additional antidepressant and sedative effects. It was first synthesized in 1979, and then subsequently studied in animals and humans in 1984 and beyond,[1] but despite demonstrating efficacy in the treatment of a variety of medical conditions including schizophrenia,[2][3][4][5] psychosis associated with Parkinson's disease,[6] depressive symptoms, and dystonia,[7] it was never marketed.[1] This was perhaps due to its capacity for producing potentially life-threatening agranulocytosis, similarly to clozapine,[8] which it closely resembles both structurally and pharmacologically.
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Formula | C19H20FN3 |
Molar mass | 309.388 g·mol−1 |
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Binding profile[9]
Receptor | Ki (nM) |
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5-HT2A | 7.9 |
5-HT2C | 18.2 |
5-HT6 | 29 |
5-HT7 | 4.6 |
M1 | 8.8 |
M2 | 71 |
M3 | 41 |
M4 | 14 |
M5 | 17 |
D1 | 85 |
D2 | 316.2 |
D3 | 254.7 |
D4 | 21 |
3-fluoro-5,11-dihydro-6H-dibenz[b,e]azepin-6-one [62662-88-8] (3)