Pipamperone
Antipsychotic drug
From Wikipedia, the free encyclopedia
Pipamperone (INN, USAN, BAN), sold under the brand name Dipiperon, 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 | Carpiperone, floropipamide, fluoropipamide, floropipamide hydrochloride (JAN), McN-JR 3345; R-3345 |
| AHFS/Drugs.com | International Drug Names |
| Routes of administration | Oral |
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| Pharmacokinetic data | |
| Elimination half-life | 17-22 hours |
| Duration of action | 0.5-1 hour |
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| ECHA InfoCard | 100.119.828 |
| Chemical and physical data | |
| Formula | C21H30FN3O2 |
| Molar mass | 375.488 g·mol−1 |
| 3D model (JSmol) | |
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Medical uses
Pipamperone was developed for use as an antipsychotic in the treatment of schizophrenia.
Pipamperone might be useful as a hallucinogen antidote or "trip killer" in blocking the effects of serotonergic psychedelics like psilocybin.[6]
Pharmacology
Pipamperone acts as an antagonist of the 5-HT2A,[7] 5-HT2B,[8] 5-HT2C[9] D2,[7] D3,[10] D4,[7][11] α1-adrenergic,[10] and α2-adrenergic receptors.[10] 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),[7][10][12] being regarded as "highly selective" for the former two sites at low doses.[12][13] Pipamperone has low and likely insignificant affinity for the H1 and mACh receptors, as well as for other serotonin and dopamine receptors.[10]
Pipamperone is considered to have been a forerunner to the atypical antipsychotics, if not an atypical antipsychotic itself, due to its prominent serotonin antagonism.[14][15][16] It is also used to normalise mood and sleep patterns and has antianxiety effects in neurotic patients.[17]
| Site | pKi |
|---|---|
| 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 |
Antidepressant effects
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).[12][19]