clopenthixol

{{Short description|Antipsychotic medication}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 306839864

| IUPAC_name = (E,Z)-2-[4-[3-(2-chlorothioxanthen-9-ylidene) propyl]piperazin-1-yl]ethanol

| image = Clopenthixol structure.svg

| width = 280

| caption =

| tradename =

| pregnancy_category =

| legal_status =

| routes_of_administration = Oral

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 982-24-1

| ATC_prefix = N05

| ATC_suffix = AF02

| PubChem = 12454

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 53904

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 11945

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

| UNII = 0A432D932A

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = D02613

| index2_label = E

| CAS_number2_Ref = {{cascite|correct|CAS}}

| CAS_number2 = 53772-84-2

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

| UNII2 = FLE878A8ZI

| C=22 | H=25 | Cl=1 | N=2 | O=1 | S=1

| smiles = Clc2cc1C(c3c(Sc1cc2)cccc3)=CCCN4CCN(CCO)CC4

}}

Clopenthixol (Sordinol), also known as clopentixol, is a typical antipsychotic drug of the thioxanthene class. It was introduced by Lundbeck in 1961.{{cite book | vauthors = Sneader W | title = Drug discovery: a history | publisher = Wiley | location = New York | year = 2005 | page = 410 | isbn = 0-471-89980-1 | url = https://books.google.com/books?id=Cb6BOkj9fK4C&pg=PA410}}

Clopenthixol is a mixture of cis and trans isomers. Zuclopenthixol, the pure cis isomer, was later introduced by Lundbeck in 1962,{{cite book | vauthors = Vela JM, Buschmann H, Holenz J, Párraga A, Torrens A | title = Antidepressants, Antipsychotics, Anxiolytics: From Chemistry and Pharmacology to Clinical Application | publisher = Wiley-VCH | location = Weinheim | year = 2007 | page = 516 | isbn = 978-3-527-31058-6 | url = https://books.google.com/books?id=yXD4QA-Y_Z0C&q=thioxanthene%201965%20pfizer&pg=PA516 }}{{Dead link|date=December 2023 |bot=InternetArchiveBot |fix-attempted=yes }} and has been much more widely used. Both drugs are equally effective as antipsychotics and have similar adverse effect profiles, but clopenthixol is half as active on a milligram-to-milligram basis and appears to produce more sedation in comparison.{{cite journal | vauthors = Gravem A, Engstrand E, Guleng RJ | title = Cis(Z)-clopenthixol and clopenthixol (Sordinol) in chronic psychotic patients. A double-blind clinical investigation | journal = Acta Psychiatrica Scandinavica | volume = 58 | issue = 5 | pages = 384–388 | date = November 1978 | pmid = 362830 | doi = 10.1111/j.1600-0447.1978.tb03570.x | s2cid = 44833311 }}

Clopenthixol is not approved for use in the United States.

{{Pharmacokinetics of long-acting injectable antipsychotics}}