Pipamperone

Last updated

Pipamperone
Pipamperone.svg
Clinical data
Trade names Dipiperon
Other namesCarpiperone, floropipamide, fluoropipamide, floropipamide hydrochloride (JAN), McN-JR 3345; R-3345
AHFS/Drugs.com International Drug Names
Routes of
administration 		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Elimination half-life 17-22 hours
Duration of action 0.5-1 hour
Identifiers
  • 1-[4-(4-fluorophenyl)-4-oxobutyl]-4-piperidin-1-ylpiperidine-4-carboxamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.119.828 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C21H30FN3O2
Molar mass 375.488 g·mol−1
3D model (JSmol)
  • Fc1ccc(cc1)C(=O)CCCN3CCC(C(=O)N)(N2CCCCC2)CC3
  • InChI=1S/C21H30FN3O2/c22-18-8-6-17(7-9-18)19(26)5-4-12-24-15-10-21(11-16-24,20(23)27)25-13-2-1-3-14-25/h6-9H,1-5,10-16H2,(H2,23,27) Yes check.svgY
  • Key:AXKPFOAXAHJUAG-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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]

Contents

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

Pipamperon Neuraxpharm, 40mg Pipamperon neuraxpharm 40mg by Danny S. - 001.JPG
Pipamperon Neuraxpharm, 40mg

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]

Affinity [18]
SitepKi
D15.61
D26.71
D36.58
D47.95
5 HT1A5.46
5 HT1B5.54
5 HT1D6.14
5 HT1E5.44
5 HT1F<5
5-HT2A8.19
5 HT55.35
5 HT76.26
α17.23
α2A6.15
α2B7.08
α2C6.25

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]

See also

References

  1. ↑ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ↑ Morton IK, Hall JM (31 October 1999). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 222–. ISBN   978-0-7514-0499-9.
  3. 1 2 Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 985–. ISBN   978-1-4757-2085-3.
  4. ↑ 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): 116–122. doi:10.1111/j.1600-0447.1977.tb00147.x. PMID   320830. S2CID   40758854.
  5. ↑ Healy D (1 July 2009). The Creation of Psychopharmacology. Harvard University Press. pp. 251–. ISBN   978-0-674-03845-5.
  6. ↑ Halman A, Kong G, Sarris J, Perkins D (January 2024). "Drug-drug interactions involving classic psychedelics: A systematic review". J Psychopharmacol. 38 (1): 3–18. doi:10.1177/02698811231211219. PMC   10851641 . PMID   37982394.
  7. 1 2 3 4 Schotte A, Janssen PF, Gommeren W, Luyten WH, Van Gompel P, Lesage AS, et al. (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. S2CID   12028979.
  8. ↑ 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): 720–727. doi:10.1016/S0022-3565(25)12346-X. PMID   8632342.
  9. ↑ 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.
  10. 1 2 3 4 5 Leyson JE (6 December 2012). "Receptor profile of antipsychotics". In Ellenbroek BA, Cools AR (eds.). Atypical Antipsychotics. Birkhäuser. pp. 62–. ISBN   978-3-0348-8448-8.
  11. ↑ 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.
  12. 1 2 3 Wade AG, Crawford GM, Nemeroff CB, Schatzberg AF, Schlaepfer T, McConnachie A, et al. (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" (PDF). Psychological Medicine. 41 (10): 2089–2097. doi:10.1017/S0033291711000158. PMID   21349239. S2CID   19189492.
  13. ↑ Abi-Dargham A, Krystal J (22 June 2000). "Serotonin Receptors as Targets of Antipsychotic Medications". In Lidow MS (ed.). Neurotransmitter Receptors in Actions of Antipsychotic Medications. CRC Press. pp. 88–. ISBN   978-1-4200-4177-4.
  14. ↑ Awouters FH, Lewi PJ (2007). "Forty years of antipsychotic Drug research--from haloperidol to paliperidone--with Dr. Paul Janssen". Arzneimittel-Forschung. 57 (10): 625–632. doi:10.1055/s-0031-1296660. PMID   18074755. S2CID   5713281.
  15. ↑ 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.
  16. ↑ Niemegeers CJ, Awouters F, Janssen PA (1990). "[Serotonin antagonism involved in the antipsychotic effect. Confirmation with ritanserine and risperidone]". L'Encéphale (in French). 16 (2): 147–151. PMID   1693560.
  17. ↑ Psychotropic Agents: Part I: Antipsychotics and Antidepressants. Springer Science & Business Media. 2012-12-06. ISBN   9783642675386.
  18. ↑ Bart A. Ellenbroek, Alexander R. Cools (eds.) (6 December 2012). Atypical Antipsychotics. Basel: Birkhäuser, pp. 62 f. ISBN   978-3-0348-8448-8.
  19. ↑ Kirk R (February 2010). "Clinical trials in CNS--SMi's eighth annual conference". IDrugs. 13 (2): 66–69. PMID   20127552.
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