Lenperone

Lenperone (Elanone-V) is a typical antipsychotic of the butyrophenone chemical class.^[1] It was first reported as an anti-emetic in 1974,^[2] and its use in treatment of acute schizophrenia was reported in 1975.^[1] Related early antipsychotic agents include declenperone and milenperone.

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 was never approved by the FDA for use in humans in the United States,^[3] but prior to 1989 it was approved for use in veterinary medicine for sedation.^[4][5][6]

Synthesis

Synthesis (cmp#21):^[7] Patent (74%):^[2] Enbodiment 19 (62%):^[8][9]

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