Pipamperone

Pipamperone

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	N05AD05 (WHO)
Identifiers
IUPAC name 1-[4-(4-fluorophenyl)-4-oxobutyl]-4-piperidin-1-ylpiperidine-4-carboxamide
Synonyms	McN-JR 3345; R-3345
CAS Number	1893-33-0 N
PubChem CID	4830
IUPHAR/BPS	92
ChemSpider	4664 Y
UNII	5402501F0W
KEGG	D02622 Y
ChEMBL	CHEMBL440294 Y
ECHA InfoCard	100.119.828
Chemical and physical data
Formula	C21H30FN3O2
Molar mass	375.480 g/mol
3D model (Jmol)	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?)

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. 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.

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.