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Pipamperone

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Pipamperone
Clinical data
Other namesMcN-JR 3345; R-3345
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
Identifiers
  • 1'-[4-(4-fluorophenyl)-4-oxobutyl]-1,4'-bipiperidine-4'-carboxamide
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)
  • 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), 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] 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.[3]

Pharmacology

Pipamperon neuraxpharm, 40mg

Pipamperone acts as an antagonist of the 5-HT2A,[4] 5-HT2B,[5] 5-HT2C[6] D2,[4] D3,[7] D4,[8][4] α1-adrenergic,[7] and α2-adrenergic receptors.[7] 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),[7][4][9] being regarded as "highly selective" for the former two sites at low doses.[9][10] Pipamperone has low and likely insignificant affinity for the H1 and mACh receptors, as well as for other serotonin and dopamine receptors.[7]

Pipamperone is considered to have been a forerunner to the atypical antipsychotics due to its prominent serotonin antagonism.[11][12][13]

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).[9][14]

Synthesis

  • U.S. patent 3,041,344
  • DE 1,235,319 
  • Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1021/jm00335a010, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1021/jm00335a010 instead.

See also

References

  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. ^ David Healy (1 July 2009). The Creation of Psychopharmacology. Harvard University Press. pp. 251–. ISBN 978-0-674-03845-5.
  4. ^ a b c d Schotte A, Janssen PF, Gommeren W, Luyten WH, Van Gompel P, Lesage AS, De Loore K, Leysen JE (1996). "Risperidone compared with new and reference antipsychotic drugs: in vitro and in vivo receptor binding". Psychopharmacology (Berl.). 124 (1–2): 57–73. PMID 8935801.
  5. ^ Wainscott DB, Lucaites VL, Kursar JD, Baez M, Nelson DL (1996). "Pharmacologic characterization of the human 5-hydroxytryptamine2B receptor: evidence for species differences". J. Pharmacol. Exp. Ther. 276 (2): 720–7. PMID 8632342.
  6. ^ Prinssen EP, Koek W, Kleven MS (2000). "The effects of antipsychotics with 5-HT(2C) receptor affinity in behavioral assays selective for 5-HT(2C) receptor antagonist properties of compounds". Eur. J. Pharmacol. 388 (1): 57–67. PMID 10657547.
  7. ^ 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.
  8. ^ Van Craenenbroeck K, Gellynck E, Lintermans B, Leysen JE, Van Tol HH, Haegeman G, Vanhoenacker P (2006). "Influence of the antipsychotic drug pipamperone on the expression of the dopamine D4 receptor". Life Sci. 80 (1): 74–81. doi:10.1016/j.lfs.2006.08.024. PMID 16978659.
  9. ^ a b c Wade AG, Crawford GM, Nemeroff CB, Schatzberg AF, Schlaepfer T, McConnachie A, Haazen L, Buntinx E (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". Psychol Med. 41 (10): 2089–97. doi:10.1017/S0033291711000158. PMID 21349239.
  10. ^ Michael S. Lidow (22 June 2000). Neurotransmitter Receptors in Actions of Antipsychotic Medications. CRC Press. pp. 88–. ISBN 978-1-4200-4177-4.
  11. ^ Awouters FH, Lewi PJ (2007). "Forty years of antipsychotic Drug research--from haloperidol to paliperidone--with Dr. Paul Janssen". Arzneimittelforschung. 57 (10): 625–32. doi:10.1055/s-0031-1296660. PMID 18074755.
  12. ^ Vanden Bussche G, Gelders YG, Heylen SL (1990). "[Development of new antipsychotic drugs]". Acta Psiquiatr Psicol Am Lat (in Spanish; Castilian). 36 (1–2): 13–25. PMID 2127339.{{cite journal}}: CS1 maint: unrecognized language (link)
  13. ^ Niemegeers CJ, Awouters F, Janssen PA (1990). "[Serotonin antagonism involved in the antipsychotic effect. Confirmation with ritanserine and risperidone]". Encephale (in French). 16 (2): 147–51. PMID 1693560.
  14. ^ Kirk R (2010). "Clinical trials in CNS--SMi's eighth annual conference". IDrugs. 13 (2): 66–9. PMID 20127552.


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