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"Trancopal" redirects here. For Trancopal Dolo, see Flupirtine.
Skeletal formula of chlormezanone
Space-filling model of the chlormezanone molecule
Systematic (IUPAC) name
Clinical data
AHFS/ International Drug Names
  • (Prescription only)
Pharmacokinetic data
Half-life 40.5 hours
80-77-3 YesY
PubChem CID 2717
DrugBank DB01178 YesY
ChemSpider 2616 YesY
UNII GP568V9G19 YesY
KEGG D00268 YesY
Chemical data
Formula C11H12ClNO3S
273.737 g/mol
 N (what is this?)  (verify)

Chlormezanone (marketed under the brandname Trancopal or Fenaprim) is a drug used as an anxiolytic and a muscle relaxant.

Its use was discontinued in many countries from 1996 on, due to rare but serious cases of toxic epidermal necrolysis.


Chlormezanone synthesis.png

  • Sterling Drug Inc., US 3082209  (1958).
  • Surrey, A. R.; Webb, W. G.; Gesler, R. M. (1958). "Central Nervous System Depressants. The Preparation of Some 2-Aryl-4-metathiazanones". Journal of the American Chemical Society 80 (13): 3469. doi:10.1021/ja01546a065.  edit


  • Wollina U, Hipler U, Seeling A, Oelschlager H (2005). "Investigations of interactions of chlormezanone racemate and its enantiomers on human keratinocytes and human leucoytes in vitro". Skin Pharmacol Physiol 18 (3): 132–138. doi:10.1159/000084910. PMID 15897685. 
  • Seeling A, Oelschläger H, Rothley D (2000). "Important pharmaceutical-chemical characteristics of the central muscle relaxant chlormezanone". Pharmazie 55 (4): 293–6. PMID 10798243. 
  • Oelschläger H, Klinger W, Rothley D, Seeling A, Bockhard H, Hofmann B, Machts H, Riederer H, Rackur H (1998). "[Cleavage and biotransformation of the central muscle relaxant chlormezanone]". Pharmazie 53 (9): 620–4. PMID 9770210. 
  • Gautier V, Vincon G, Demotes-Mainard F, Albin H (1990). "[Pharmacokinetics of chlormezanone in healthy volunteers] (original in French)". Pharmazie 45 (4): 315–9. PMID 2399514.