Chemistry:Pipamperone

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Short description: Antipsychotic drug
Pipamperone
Pipamperone.svg
Clinical data
Trade namesDipiperon
Other namesMcN-JR 3345; R-3345
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • BR: Class C1 (Other controlled substances)
Pharmacokinetic data
Elimination half-life17-22 hours
Duration of action0.5-1 hour
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC21H30FN3O2
Molar mass375.488 g·mol−1
3D model (JSmol)
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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

Pipamperon Neuraxpharm, 40mg

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]

Affinity[16]
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

  1. ↑ 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. ↑ 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. 
  3. ↑ "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. 
  4. ↑ 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. ↑ 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. 
  6. ↑ "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. 
  7. ↑ "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. ↑ 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. 
  9. ↑ "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. ↑ 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. 
  11. ↑ "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. 
  12. ↑ "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. 
  13. ↑ "[Development of new antipsychotic drugs]" (in es). Acta Psiquiatrica y Psicologica de America Latina 36 (1–2): 13–25. 1990. PMID 2127339. 
  14. ↑ "[Serotonin antagonism involved in the antipsychotic effect. Confirmation with ritanserine and risperidone]" (in fr). L'Encéphale 16 (2): 147–151. 1990. PMID 1693560. 
  15. ↑ (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. 
  16. ↑ Bart A. Ellenbroek, Alexander R. Cools (eds.) (6 December 2012). Atypical Antipsychotics. Basel: Birkhäuser, pp. 62 f. ISBN:978-3-0348-8448-8.
  17. ↑ "Clinical trials in CNS--SMi's eighth annual conference". IDrugs 13 (2): 66–69. February 2010. PMID 20127552. 



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