Chemistry:Lenperone
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| Trade names | Elanone-V |
| Routes of administration | Oral |
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| Formula | C22H23F2NO2 |
| Molar mass | 371.428 g·mol−1 |
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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
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
- ↑ 1.0 1.1 "Treatment of acute schizophrenia with a new butyrophenone-lenperone". Journal of Clinical Pharmacology 15 (2–3): 187–190. 1975. doi:10.1002/j.1552-4604.1975.tb02355.x. PMID 1091666.
- ↑ 2.0 2.1 Ward JW, Leonard CA, "Antiemetic compositions containing piperidine derivatives", FR patent 2227868, published 1974-11-29
- ↑ "Neuroleptanalgesia for acute abdominal pain: a systematic review". Journal of Pain Research 12: 787–801. 2019. doi:10.2147/JPR.S187798. PMID 30881092. "Table 1. Marketed butyrophenones with approval status and indication".
- ↑ Booth NJ (1982). "Psychotropic Agents". in Booth NH, McDonald LE. Veterinary Pharmacology and Therapeutics (5th ed.). Ames, Iowa: Iowa State University Press. pp. 321–345.
- ↑ "Effect of lenperone hydrochloride on gastroesophageal sphincter pressure in healthy dogs". Canadian Journal of Veterinary Research 53 (2): 248–250. April 1989. PMID 2565757.
- ↑ 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"
- ↑ "Aroylpiperidines and pyrrolidines. A new class of potent central nervous system depressants". Journal of Medicinal Chemistry 13 (1): 1–6. January 1970. doi:10.1021/jm00295a001. PMID 5460893.
- ↑ Yanbiao K, Jie L, CN patent 107011133, issued 2017, assigned to University of Science and Technology of China USTC.
- ↑ "Organopromoted Selectivity-Switchable Synthesis of Polyketones". Organic Letters 19 (20): 5593–5596. October 2017. doi:10.1021/acs.orglett.7b02731. PMID 28981291.
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