Lenperone

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Lenperone
Clinical data
Trade namesElanone-V
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • 4-[4-(4-Fluorobenzoyl)piperidin-1-yl]-1-(4-fluorophenyl)butan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
E number{{#property:P628}}
CompTox Dashboard (EPA)
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
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Chemical and physical data
FormulaC22H23F2NO2
Molar mass371.428 g·mol−1
3D model (JSmol)
  • C1CN(CCC1C(=O)C2=CC=C(C=C2)F)CCCC(=O)C3=CC=C(C=C3)F
  • 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.[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 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

[edit | edit source]
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

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

References

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  1. ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  2. ^ a b FR 2227868, Ward JW, Leonard CA, "Antiemetic compositions containing piperidine derivatives", published Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value). 
  3. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
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  8. ^ CN 107011133, Yanbiao K, Jie L, issued Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)., assigned to University of Science and Technology of China USTC. 
  9. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
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