Lenperone

Lenperone

Clinical data
Trade names	Elanone-V
Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name 4-[4-(4-Fluorobenzoyl)piperidin-1-yl]-1-(4-fluorophenyl)butan-1-one
CAS Number	24678-13-5 HCl: 24677-86-9
PubChem CID	32593
ChemSpider	30207
UNII	13P4GX22ES HCl: 96Q0TL6O3G Y
KEGG	D02668
ChEMBL	ChEMBL316004
CompTox Dashboard (EPA)	DTXSID7046120
ECHA InfoCard	100.042.166
Chemical and physical data
Formula	C22H23F2NO2
Molar mass	371.428 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1CN(CCC1C(=O)C2=CC=C(C=C2)F)CCCC(=O)C3=CC=C(C=C3)F
InChI InChI=1S/C22H23F2NO2/c23-19-7-3-16(4-8-19)21(26)2-1-13-25-14-11-18(12-15-25)22(27)17-5-9-20(24)10-6-17/h3-10,18H,1-2,11-15H2 Key:WCIBOXFOUGQLFC-UHFFFAOYSA-N

Lenperone (Elanone-V) is a typical antipsychotic of the butyrophenone chemical class. It was first reported as an anti-emetic in 1974, and its use in treatment of acute schizophrenia was reported in 1975. Related early antipsychotic agents include declenperone and milenperone.

Lenperone was never approved by the FDA for use in humans in the United States, but prior to 1989 it was approved for use in veterinary medicine for sedation.

Synthesis

Synthesis (cmp#21): Patent (74%): Enbodiment 19 (62%):

The alkylation between 2-(3-chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane [3308-94-9] (1) and 4-(4-fluorobenzoyl)piperidine [56346-57-7] (2) gives 2-(p-fluorophenyl)-2-{3-[4-(p-fluorobenzoyl)piperidino]propyl}-1,3-dioxolane, CID:20318874 (3). Deprotection of the ketal function completes the synthesis of lenperone (4).

See also

• Glemanserin
• Pruvanserin
• Roluperidone
• Volinanserin

Chemically related drugs containing the same 4-(p-fluorobenzoyl)piperidine group:

• Altanserin
• Ketanserin
• Setoperone
• Lidanserin