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Pipamperone

From Wikipedia, the free encyclopedia
Antipsychotic drug

Not to be confused withPirenperone.
Pharmaceutical compound
Pipamperone
Clinical data
Trade namesDipiperon
Other namesCarpiperone, floropipamide, fluoropipamide, floropipamide hydrochloride (JAN), McN-JR 3345; R-3345
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Eliminationhalf-life17-22 hours
Duration of action0.5-1 hour
Identifiers
  • 1-[4-(4-fluorophenyl)-4-oxobutyl]-4-piperidin-1-ylpiperidine-4-carboxamide
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.119.828Edit this at Wikidata
Chemical and physical data
FormulaC21H30FN3O2
Molar mass375.488 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) checkY
  • Key:AXKPFOAXAHJUAG-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Pipamperone (INN,USAN,BAN), sold under the brand nameDipiperon, is atypical antipsychotic of thebutyrophenone family used in the treatment ofschizophrenia[2][3] and as a sleep aid for depression.[4] It is or has been marketed under brand names includingDipiperon,Dipiperal,Piperonil,Piperonyl, andPropitan.[3] Pipamperone was discovered atJanssen Pharmaceutica in 1961, and enteredclinical trials in theUnited States in 1963.[5]

Medical uses

[edit]

Pipamperone was developed for use as anantipsychotic in the treatment ofschizophrenia.

Pipamperone might be useful as ahallucinogen antidote or "trip killer" in blocking the effects ofserotonergic psychedelics likepsilocybin.[6]

Pharmacology

[edit]
Pipamperon Neuraxpharm, 40mg

Pipamperone acts as anantagonist of the5-HT2A,[7]5-HT2B,[8]5-HT2C[9]D2,[7]D3,[10]D4,[7][11]α1-adrenergic,[10] andα2-adrenergic receptors.[10] It shows much higheraffinity 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 theH1 andmACh receptors, as well as for otherserotonin anddopamine receptors.[10]

Pipamperone is considered to have been a forerunner to theatypical antipsychotics, if not an atypical antipsychotic itself, due to its prominentserotonin 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

[edit]

Low-dose pipamperone (5 mg twice daily) has been found to accelerate and enhance theantidepressant effect ofcitalopram (40 mg once daily), in a combination (citalopram/pipamperone) referred to asPipCit (code namePNB-01).[12][19]

See also

[edit]

References

[edit]
  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. Retrieved2023-08-16.
  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. ^abElks 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. ^abcdSchotte 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. ^abcdeLeyson 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. ^abcWade 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.
Typical
Disputed
Atypical
Others
α1
Agonists
Antagonists
α2
Agonists
Antagonists
β
Agonists
Antagonists
D1-like
Agonists
PAMs
Antagonists
D2-like
Agonists
Antagonists
5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT3–7
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
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