Chlormezanone: Difference between revisions

{{Short description|Withdrawn anxiolytic and muscle relaxant}}

| Watchedfields = changed

| verifiedrevid = 460031099

| alt = Skeletal formula of chlormezanone

| width = 210

| image2 = Chlormezanone-3D-spacefill.png

| alt2 = Space-filling model of the chlormezanone molecule

| width2 = 170

| IUPHAR_ligand = 7323

| KEGG_Ref = {{keggcite|correct|kegg}}

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1200714

<!--Chemical data-->

| C=11 | H=12 | Cl=1 | N=1 | O=3 | S=1

| smiles = O=S1(CCC(N(C)C1C2=CC=C(C=C2)Cl)=O)=O

'''Chlormezanone''' (marketed under the [[brandname]] '''Trancopal''' or '''Fenaprim''') is a [[drug]] used as an [[anxiolytic]] and a [[muscle relaxant]].<ref>{{cite book | vauthors = Turner P, Volan G, Wiseman H |title=Drugs Handbook |date=1997 |publisher=Palgrave Macmillan |location=UK |isbn=978-1-349-13937-8 | url = https://books.google.com/books?id=0_OxCwAAQBAJ&dq=Chlormezanone+anxiolytic&pg=PA20 | page = 20 }}</ref>

Its use was discontinued in many countries in 1996 due to rare but serious cases of [[toxic epidermal necrolysis]].<ref name="Lerch_2018">{{cite journal | vauthors = Lerch M, Mainetti C, Terziroli Beretta-Piccoli B, Harr T | title = Current Perspectives on Stevens-Johnson Syndrome and Toxic Epidermal Necrolysis | journal = Clinical Reviews in Allergy & Immunology | volume = 54 | issue = 1 | pages = 147–176 | date = February 2018 | pmid = 29188475 | doi = 10.1007/s12016-017-8654-z | s2cid = 46796285 }}</ref>

== Synthesis ==

[[File:Synthesis of chlormezanone.svg|thumb|center|400px|Chlormezanone synthesis<ref>{{Cite patent |country=US |number=3082209 | title = 4-metathiazanone derivatives and their preparation |gdate = 1958 | inventor = Surrey AR | assign1 = Sterling Drug Inc.}}</ref><ref>{{Cite journal | vauthors = Surrey AR, Webb WG, Gesler RM | journal = Journal of the American Chemical Society | title = Central Nervous System Depressants. The Preparation of Some 2-Aryl-4-metathiazanones | volume = 80 | issue = 13 | pages = 3469–3471 | year = 1958 | doi = 10.1021/ja01546a065 }}</ref>]]

{{Reflist}}

== Further reading ==

{{refbegin}}

* {{cite journal | vauthors = Wollina U, Hipler UC, Seeling A, Oelschlager H | title = Investigations of interactions of chlormezanone racemate and its enantiomers on human keratinocytes and human leucoytes in vitro | journal = Skin Pharmacology and Physiology | volume = 18 | issue = 3 | pages = 132–138 | year = 2005 | pmid = 15897685 | doi = 10.1159/000084910 | s2cid = 36642315 }}

* {{cite journal | vauthors = Seeling A, Oelschläger H, Rothley D | title = [Important pharmaceutical-chemical characteristics of the central muscle relaxant chlormezanone] | journal = Die Pharmazie | volume = 55 | issue = 4 | pages = 293–296 | date = April 2000 | pmid = 10798243 }}

* {{cite journal | vauthors = Oelschläger H, Klinger W, Rothley D, Seeling A, Bockhard H, Hofmann B, Machts H, Riederer H, Rackur H | display-authors = 6 | title = [Cleavage and biotransformation of the central muscle relaxant chlormezanone] | journal = Die Pharmazie | volume = 53 | issue = 9 | pages = 620–624 | date = September 1998 | pmid = 9770210 }}

* {{cite journal | vauthors = Gautier V, Vinçon G, Demotes-Mainard F, Albin H | title = [Pharmacokinetics of chlormezanone in healthy volunteers] | journal = Therapie | volume = 45 | issue = 4 | pages = 315–319 | year = 1990 | pmid = 2399514 }}

{{refend}}

{{GABAAR PAMs}}

[[Category:Chloroarenes]]

[[Category:Hepatotoxins]]

[[Category:GABAA receptor positive allosteric modulators]]