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 namesElanone-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
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.042.166
Chemical and physical data
FormulaC22H23F2NO2
Molar mass371.428 g·mol−1
3D model (JSmol)
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

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

References
  1. Harris M (1975). "Treatment of Acute Schizophrenia with a New Butyrophenone-Lenperone". Journal of Clinical Pharmacology. 15 (2–3): 187–90. doi:10.1002/j.1552-4604.1975.tb02355.x. PMID 1091666. S2CID 28602974.
  2. FR 2227868, Ward, John Wesley & Leonard, Charles A., "Antiemetic compositions containing piperidine derivatives", published 1974-11-29
  3. Table 1. Marketed butyrophenones with approval status and indication in Miller AC, Khan AM, Castro Bigalli AA, Sewell KA, King AR, Ghadermarzi S, et al. (2019). "Neuroleptanalgesia for acute abdominal pain: a systematic review". Journal of Pain Research. 12: 787–801. doi:10.2147/JPR.S187798. PMC 6396833. PMID 30881092.
  4. Booth NJ (1982). "Psychotropic Agents". In Booth NH, McDonald LE (ed.). Veterinary Pharmacology and Therapeutics (5th ed.). Ames, Iowa: Iowa State University Press. pp. 321–345.
  5. Johnson SE, Zelner A, Sherding RG (April 1989). "Effect of lenperone hydrochloride on gastroesophageal sphincter pressure in healthy dogs". Canadian Journal of Veterinary Research. 53 (2): 248–50. PMC 1255555. PMID 2565757.
  6. FDA Veterinarian. U.S. Department of Health and Human Services, Public Health Service, Food and Drug Administration, Center for Veterinary Medicine. 1988. The firm requested withdrawal of approval because the products are no longer being marketed. Effective date: July 13, 1989
  7. Duncan, Robert L.; Helsley, Grover C.; Welstead, William J.; DaVanzo, John P.; Funderburk, William H.; Lunsford, Carl D. (1970). "Aroylpiperidines and pyrrolidines. New class of potent central nervous system depressants". Journal of Medicinal Chemistry. 13 (1): 1–6. doi:10.1021/jm00295a001.
  8. Kang Yanbiao & Liu Jie, CN 107011133 (2017 to University of Science and Technology of China USTC).
  9. Liu, Jie; Hu, Kang-Fei; Qu, Jian-Ping; Kang, Yan-Biao (2017). "Organopromoted Selectivity-Switchable Synthesis of Polyketones". Organic Letters. 19 (20): 5593–5596. doi:10.1021/acs.orglett.7b02731.
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