Pipamperone

Pipamperone

Clinical data
Trade names	Dipiperon
Other names	McN-JR 3345; R-3345
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	N05AD05 (WHO)
Pharmacokinetic data
Elimination half-life	17-22 hours
Duration of action	0.5-1 hour
Identifiers
IUPAC name 1-[4-(4-fluorophenyl)-4-oxobutyl]-4-piperidin-1-ylpiperidine-4-carboxamide
CAS Number	1893-33-0 N
PubChem CID	4830
IUPHAR/BPS	92
DrugBank	DB09286 Y
ChemSpider	4664 Y
UNII	5402501F0W
KEGG	D02622 Y
ChEMBL	ChEMBL440294 Y
CompTox Dashboard (EPA)	DTXSID8048369
ECHA InfoCard	100.119.828
Chemical and physical data
Formula	C21H30FN3O2
Molar mass	375.488 g·mol−1
3D model (JSmol)	Interactive image
SMILES Fc1ccc(cc1)C(=O)CCCN3CCC(C(=O)N)(N2CCCCC2)CC3
InChI 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) Y Key:AXKPFOAXAHJUAG-UHFFFAOYSA-N Y
NY (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 and as a sleep aid for depression. It is or has been marketed under brand names including Dipiperon, Dipiperal, Piperonil, Piperonyl, and Propitan. Pipamperone was discovered at Janssen Pharmaceutica in 1961, and entered clinical trials in the United States in 1963.

Pharmacology

Pipamperon Neuraxpharm, 40mg

Pipamperone acts as an antagonist of the 5-HT_2A,5-HT_2B,5-HT_2CD₂,D₃,D₄,α₁-adrenergic, and α₂-adrenergic receptors. It shows much higher affinity for the 5-HT_2A 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-HT_2A receptor), being regarded as "highly selective" for the former two sites at low doses. Pipamperone has low and likely insignificant affinity for the H₁ and mACh receptors, as well as for other serotonin and dopamine receptors.

Pipamperone is considered to have been a forerunner to the atypical antipsychotics, if not an atypical antipsychotic itself, due to its prominent serotonin antagonism. It is also used to normalise mood and sleep patterns and has antianxiety effects in neurotic patients.

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).

See also

• Clozapine
• Melperone
• Pimozide
• Piritramide
• Risperidone