Chemistry:Pipamperone
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| Trade names | Dipiperon |
| Other names | 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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| Chemical and physical data | |
| Formula | C21H30FN3O2 |
| Molar mass | 375.488 g·mol−1 |
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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[1][2] and as a sleep aid for depression.[3] It is or has been marketed under brand names including Dipiperon, Dipiperal, Piperonil, Piperonyl, and Propitan.[2] Pipamperone was discovered at Janssen Pharmaceutica in 1961, and entered clinical trials in the United States in 1963.[4]
Pharmacology
Pipamperone acts as an antagonist of the 5-HT2A,[5] 5-HT2B,[6] 5-HT2C[7] D2,[5] D3,[8] D4,[5][9] α1-adrenergic,[8] and α2-adrenergic receptors.[8] 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),[5][8][10] being regarded as "highly selective" for the former two sites at low doses.[10][11] Pipamperone has low and likely insignificant affinity for the H1 and mACh receptors, as well as for other serotonin and dopamine receptors.[8]
Pipamperone is considered to have been a forerunner to the atypical antipsychotics, if not an atypical antipsychotic itself, due to its prominent serotonin antagonism.[12][13][14] It is also used to normalise mood and sleep patterns and has antianxiety effects in neurotic patients.[15]
| 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).[10][17]
See also
References
- ↑ Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. 31 October 1999. pp. 222–. ISBN 978-0-7514-0499-9. https://books.google.com/books?id=mqaOMOtk61IC&pg=PA222.
- ↑ 2.0 2.1 The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 985–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA985.
- ↑ "Sleep disorders in patients with severe mental depression: double-blind placebo-controlled evaluation of the value of pipamperone (Dipiperon)". Acta Psychiatrica Scandinavica 55 (2): 116–122. February 1977. doi:10.1111/j.1600-0447.1977.tb00147.x. PMID 320830.
- ↑ The Creation of Psychopharmacology. Harvard University Press. 1 July 2009. pp. 251–. ISBN 978-0-674-03845-5. https://books.google.com/books?id=6O2rPJnyhj0C&pg=PA251.
- ↑ 5.0 5.1 5.2 5.3 "Risperidone compared with new and reference antipsychotic drugs: in vitro and in vivo receptor binding". Psychopharmacology 124 (1–2): 57–73. March 1996. doi:10.1007/bf02245606. PMID 8935801.
- ↑ "Pharmacologic characterization of the human 5-hydroxytryptamine2B receptor: evidence for species differences". The Journal of Pharmacology and Experimental Therapeutics 276 (2): 720–727. February 1996. PMID 8632342. http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=8632342.
- ↑ "The effects of antipsychotics with 5-HT(2C) receptor affinity in behavioral assays selective for 5-HT(2C) receptor antagonist properties of compounds". European Journal of Pharmacology 388 (1): 57–67. January 2000. doi:10.1016/s0014-2999(99)00859-6. PMID 10657547.
- ↑ 8.0 8.1 8.2 8.3 8.4 "Receptor profile of antipsychotics". Atypical Antipsychotics. Birkhäuser. 6 December 2012. pp. 62–. ISBN 978-3-0348-8448-8. https://books.google.com/books?id=08kGCAAAQBAJ&pg=PA62.
- ↑ "Influence of the antipsychotic drug pipamperone on the expression of the dopamine D4 receptor". Life Sciences 80 (1): 74–81. December 2006. doi:10.1016/j.lfs.2006.08.024. PMID 16978659.
- ↑ 10.0 10.1 10.2 "Citalopram plus low-dose pipamperone versus citalopram plus placebo in patients with major depressive disorder: an 8-week, double-blind, randomized study on magnitude and timing of clinical response". Psychological Medicine 41 (10): 2089–2097. October 2011. doi:10.1017/S0033291711000158. PMID 21349239. https://eprints.gla.ac.uk/57374/1/id57374.pdf.
- ↑ "Serotonin Receptors as Targets of Antipsychotic Medications". Neurotransmitter Receptors in Actions of Antipsychotic Medications. CRC Press. 22 June 2000. pp. 88–. ISBN 978-1-4200-4177-4. https://books.google.com/books?id=HIHLBQAAQBAJ&pg=PA88.
- ↑ "Forty years of antipsychotic Drug research--from haloperidol to paliperidone--with Dr. Paul Janssen". Arzneimittel-Forschung 57 (10): 625–632. 2007. doi:10.1055/s-0031-1296660. PMID 18074755.
- ↑ "[Development of new antipsychotic drugs]" (in es). Acta Psiquiatrica y Psicologica de America Latina 36 (1–2): 13–25. 1990. PMID 2127339.
- ↑ "[Serotonin antagonism involved in the antipsychotic effect. Confirmation with ritanserine and risperidone]" (in fr). L'Encéphale 16 (2): 147–151. 1990. PMID 1693560.
- ↑ (in en) Psychotropic Agents: Part I: Antipsychotics and Antidepressants. Springer Science & Business Media. 2012-12-06. ISBN 9783642675386. https://books.google.com/books?id=oK7tCAAAQBAJ&q=pipamperone+mania&pg=PA36.
- ↑ Bart A. Ellenbroek, Alexander R. Cools (eds.) (6 December 2012). Atypical Antipsychotics. Basel: Birkhäuser, pp. 62 f. ISBN:978-3-0348-8448-8.
- ↑ "Clinical trials in CNS--SMi's eighth annual conference". IDrugs 13 (2): 66–69. February 2010. PMID 20127552.
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