Pipamperone

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Pipamperone
Pipamperone.svg
Clinical data
SynonymsMcN-JR 3345; R-3345
AHFS/Drugs.comInternational Drug Names
Routes of
administration
Oral
ATC code
Pharmacokinetic data
Elimination half-life17-22 hours
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.119.828 Edit this at Wikidata
Chemical and physical data
FormulaC21H30FN3O2
Molar mass375.480 g/mol 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[edit]

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]

Antidepressant effects[edit]

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][16]

See also[edit]

References[edit]

  1. ^ Dr. Ian Morton; I.K. Morton; Judith M. Hall (31 October 1999). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 222–. ISBN 978-0-7514-0499-9.
  2. ^ a b J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 985–. ISBN 978-1-4757-2085-3.
  3. ^ Ansoms C, Backer-Dierick GD, Vereecken JL (February 1977). "Sleep disorders in patients with severe mental depression: double-blind placebo-controlled evaluation of the value of pipamperone (Dipiperon)". Acta Psychiatrica Scandinavica. 55 (2): 116–22. doi:10.1111/j.1600-0447.1977.tb00147.x. PMID 320830.
  4. ^ David Healy (1 July 2009). The Creation of Psychopharmacology. Harvard University Press. pp. 251–. ISBN 978-0-674-03845-5.
  5. ^ a b c d Schotte A, Janssen PF, Gommeren W, Luyten WH, Van Gompel P, Lesage AS, De Loore K, Leysen JE (March 1996). "Risperidone compared with new and reference antipsychotic drugs: in vitro and in vivo receptor binding". Psychopharmacology. 124 (1–2): 57–73. doi:10.1007/bf02245606. PMID 8935801.
  6. ^ Wainscott DB, Lucaites VL, Kursar JD, Baez M, Nelson DL (February 1996). "Pharmacologic characterization of the human 5-hydroxytryptamine2B receptor: evidence for species differences". The Journal of Pharmacology and Experimental Therapeutics. 276 (2): 720–7. PMID 8632342.
  7. ^ Prinssen EP, Koek W, Kleven MS (January 2000). "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. doi:10.1016/s0014-2999(99)00859-6. PMID 10657547.
  8. ^ a b c d e Bart A. Ellenbroek; Alexander R. Cools (6 December 2012). Atypical Antipsychotics. Birkhäuser. pp. 62–. ISBN 978-3-0348-8448-8.
  9. ^ Van Craenenbroeck K, Gellynck E, Lintermans B, Leysen JE, Van Tol HH, Haegeman G, Vanhoenacker P (December 2006). "Influence of the antipsychotic drug pipamperone on the expression of the dopamine D4 receptor". Life Sciences. 80 (1): 74–81. doi:10.1016/j.lfs.2006.08.024. PMID 16978659.
  10. ^ a b c Wade AG, Crawford GM, Nemeroff CB, Schatzberg AF, Schlaepfer T, McConnachie A, Haazen L, Buntinx E (October 2011). "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): 2089–97. doi:10.1017/S0033291711000158. PMID 21349239.
  11. ^ Michael S. Lidow (22 June 2000). Neurotransmitter Receptors in Actions of Antipsychotic Medications. CRC Press. pp. 88–. ISBN 978-1-4200-4177-4.
  12. ^ Awouters FH, Lewi PJ (2007). "Forty years of antipsychotic Drug research--from haloperidol to paliperidone--with Dr. Paul Janssen". Arzneimittel-Forschung. 57 (10): 625–32. doi:10.1055/s-0031-1296660. PMID 18074755.
  13. ^ Vanden Bussche G, Gelders YG, Heylen SL (1990). "[Development of new antipsychotic drugs]". Acta Psiquiatrica y Psicologica de America Latina (in Spanish). 36 (1–2): 13–25. PMID 2127339.
  14. ^ Niemegeers CJ, Awouters F, Janssen PA (1990). "[Serotonin antagonism involved in the antipsychotic effect. Confirmation with ritanserine and risperidone]". L'Encephale (in French). 16 (2): 147–51. PMID 1693560.
  15. ^ Psychotropic Agents: Part I: Antipsychotics and Antidepressants. Springer Science & Business Media. 2012-12-06. ISBN 9783642675386.
  16. ^ Kirk R (February 2010). "Clinical trials in CNS--SMi's eighth annual conference". IDrugs. 13 (2): 66–9. PMID 20127552.