Pipamperone (INN, USAN, BAN), also known as carpiperone and floropipamide or fluoropipamide, and as floropipamide hydrochloride (JAN), is a typical antipsychotic of the butyrophenone family used in the treatment of schizophrenia[2][3] and as a sleep aid for depression.[4] It is or has been marketed under brand names including Dipiperon, Dipiperal, Piperonil, Piperonyl, and Propitan.[3] Pipamperone was discovered at Janssen Pharmaceutica in 1961, and entered clinical trials in the United States in 1963.[5]
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Trade names | Dipiperon |
Other names | McN-JR 3345; R-3345 |
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Routes of administration | Oral |
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Elimination half-life | 17-22 hours |
Duration of action | 0.5-1 hour |
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ECHA InfoCard | 100.119.828 |
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Formula | C21H30FN3O2 |
Molar mass | 375.488 g·mol−1 |
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Pipamperone acts as an antagonist of the 5-HT2A,[6] 5-HT2B,[7] 5-HT2C[8] D2,[6] D3,[9] D4,[6][10] α1-adrenergic,[9] and α2-adrenergic receptors.[9] It shows much higher affinity for the 5-HT2A and D4 receptors over the D2 receptor (15-fold in the case of the D4 receptor, and even higher in the case of the 5-HT2A receptor),[6][9][11] being regarded as "highly selective" for the former two sites at low doses.[11][12] Pipamperone has low and likely insignificant affinity for the H1 and mACh receptors, as well as for other serotonin and dopamine receptors.[9]
Pipamperone is considered to have been a forerunner to the atypical antipsychotics, if not an atypical antipsychotic itself, due to its prominent serotonin antagonism.[13][14][15] It is also used to normalise mood and sleep patterns and has antianxiety effects in neurotic patients.[16]
Site | pKi |
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D1 | 5.61 |
D2 | 6.71 |
D3 | 6.58 |
D4 | 7.95 |
5 HT1A | 5.46 |
5 HT1B | 5.54 |
5 HT1D | 6.14 |
5 HT1E | 5.44 |
5 HT1F | <5 |
5-HT2A | 8.19 |
5 HT5 | 5.35 |
5 HT7 | 6.26 |
α1 | 7.23 |
α2A | 6.15 |
α2B | 7.08 |
α2C | 6.25 |
Low-dose pipamperone (5 mg twice daily) has been found to accelerate and enhance the antidepressant effect of citalopram (40 mg once daily), in a combination (citalopram/pipamperone) referred to as PipCit (code name PNB-01).[11][18]