Pipamperone

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Pipamperone
Pipamperone.svg
Systematic (IUPAC) name
1-[4-(4-fluorophenyl)-4-oxobutyl]-4-piperidin-1-ylpiperidine-4-carboxamide
Clinical data
AHFS/Drugs.com International Drug Names
Routes of
administration		 Oral
Identifiers
CAS Number 1893-33-0 N
ATC code N05AD05 (WHO)
PubChem CID: 4830
IUPHAR/BPS 92
ChemSpider 4664 YesY
UNII 5402501F0W YesY
KEGG D02622 YesY
ChEMBL CHEMBL440294 YesY
Synonyms McN-JR 3345; R-3345
Chemical data
Formula C21H30FN3O2
Molecular mass 375.480 g/mol
  • 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) YesY
  • Key:AXKPFOAXAHJUAG-UHFFFAOYSA-N YesY
 NYesY (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,[4][8] 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, and even higher in the case of the 5-HT2A receptor),[4][7][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, if not an atypical antipsychotic itself, 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]

See also

References

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  9. ↑ 9.0 9.1 9.2 Lua error in package.lua at line 80: module 'strict' not found.
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  13. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  14. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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