Lenperone

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = 4-[4-(4-Fluorobenzoyl)piperidin-1-yl]-1-(4-fluorophenyl)butan-1-one

| image = Lenperone.svg

| width = 250

| tradename = Elanone-V

| pregnancy_category =

| legal_status = Rx-only

| routes_of_administration = Oral

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| index2_label = HCl

| CAS_number = 24678-13-5

| CAS_number2 = 24677-86-9

| ATC_prefix = none

| ATC_suffix =

| PubChem = 32593

| ChemSpiderID = 30207

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 13P4GX22ES

| UNII2_Ref = {{fdacite|correct|FDA}}

| UNII2 = 96Q0TL6O3G

| KEGG = D02668

| ChEMBL = 316004

| C=22 | H=23 | F=2 | N=1 | O=2

| smiles = C1CN(CCC1C(=O)C2=CC=C(C=C2)F)CCCC(=O)C3=CC=C(C=C3)F

| StdInChI = 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

| StdInChIKey = WCIBOXFOUGQLFC-UHFFFAOYSA-N

}}

Lenperone (Elanone-V) is a typical antipsychotic of the butyrophenone chemical class.{{cite journal | vauthors = Harris M | title = Treatment of acute schizophrenia with a new butyrophenone-lenperone | journal = Journal of Clinical Pharmacology | volume = 15 | issue = 2–3 | pages = 187–190 | year = 1975 | pmid = 1091666 | doi = 10.1002/j.1552-4604.1975.tb02355.x | s2cid = 28602974 }} It was first reported as an anti-emetic in 1974,{{cite patent | title = Antiemetic compositions containing piperidine derivatives | inventor = Ward JW, Leonard CA | country = FR | number = 2227868 | pubdate = 1974-11-29 }} 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,{{cite journal | vauthors = Miller AC, Khan AM, Castro Bigalli AA, Sewell KA, King AR, Ghadermarzi S, Mao Y, Zehtabchi S | display-authors = 6 | title = Neuroleptanalgesia for acute abdominal pain: a systematic review | journal = Journal of Pain Research | volume = 12 | pages = 787–801 | year = 2019 | pmid = 30881092 | pmc = 6396833 | doi = 10.2147/JPR.S187798 | quote = Table 1. Marketed butyrophenones with approval status and indication | doi-access = free }} but prior to 1989 it was approved for use in veterinary medicine for sedation.{{cite book | author = Booth NJ | chapter = Psychotropic Agents | editor = Booth NH, McDonald LE | title = Veterinary Pharmacology and Therapeutics | edition = 5th | location = Ames, Iowa | publisher = Iowa State University Press | date = 1982 | pages = 321–345 }}{{cite journal | vauthors = Johnson SE, Zelner A, Sherding RG | title = Effect of lenperone hydrochloride on gastroesophageal sphincter pressure in healthy dogs | journal = Canadian Journal of Veterinary Research | volume = 53 | issue = 2 | pages = 248–250 | date = April 1989 | pmid = 2565757 | pmc = 1255555 }}{{cite book | title = FDA Veterinarian | publisher = U.S. Department of Health and Human Services, Public Health Service, Food and Drug Administration, Center for Veterinary Medicine | date = 1988 | quote = The firm requested withdrawal of approval because the products are no longer being marketed. Effective date: July 13, 1989 }}

Synthesis

File:Lenperone synthesis.svg

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, [https://pubchem.ncbi.nlm.nih.gov/compound/20318874 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

{{Reflist}}

{{Antipsychotics}}

{{Cholinergics}}

{{Dopaminergics}}

{{Histaminergics}}

Category:Butyrophenone antipsychotics

Category:4-Fluorophenyl compounds

Category:Piperidines

Category:Typical antipsychotics

Category:Veterinary drugs

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