Chemistry:Chlormezanone

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Short description: Withdrawn anxiolytic and muscle relaxant
Chlormezanone
Skeletal formula of chlormezanone
Space-filling model of the chlormezanone molecule
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration
Oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Elimination half-life40.5 hours
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC11H12ClNO3S
Molar mass273.73 g·mol−1
3D model (JSmol)
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Chlormezanone (marketed under the brandname Trancopal or Fenaprim) is a drug used as an anxiolytic and a muscle relaxant.[1]

Its use was discontinued in many countries in 1996 due to rare but serious cases of toxic epidermal necrolysis.[2]

Synthesis

Chlormezanone synthesis[3][4]

References

  1. Drugs Handbook. UK: Palgrave Macmillan. 1997. p. 20. ISBN 978-1-349-13937-8. https://books.google.com/books?id=0_OxCwAAQBAJ&dq=Chlormezanone+anxiolytic&pg=PA20. 
  2. "Current Perspectives on Stevens-Johnson Syndrome and Toxic Epidermal Necrolysis". Clinical Reviews in Allergy & Immunology 54 (1): 147–176. February 2018. doi:10.1007/s12016-017-8654-z. PMID 29188475. 
  3. Surrey AR, "4-metathiazanone derivatives and their preparation", US patent 3082209, issued 1958, assigned to Sterling Drug Inc.
  4. "Central Nervous System Depressants. The Preparation of Some 2-Aryl-4-metathiazanones". Journal of the American Chemical Society 80 (13): 3469–3471. 1958. doi:10.1021/ja01546a065. 

Further reading

  • "Investigations of interactions of chlormezanone racemate and its enantiomers on human keratinocytes and human leucoytes in vitro". Skin Pharmacology and Physiology 18 (3): 132–138. 2005. doi:10.1159/000084910. PMID 15897685. 
  • "[Important pharmaceutical-chemical characteristics of the central muscle relaxant chlormezanone]". Die Pharmazie 55 (4): 293–296. April 2000. PMID 10798243. 
  • "[Cleavage and biotransformation of the central muscle relaxant chlormezanone]". Die Pharmazie 53 (9): 620–624. September 1998. PMID 9770210. 
  • "[Pharmacokinetics of chlormezanone in healthy volunteers]". Therapie 45 (4): 315–319. 1990. PMID 2399514.