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Chlormezanone

From Wikipedia, the free encyclopedia
Withdrawn anxiolytic and muscle relaxant
"Trancopal" redirects here. For Trancopal Dolo, seeFlupirtine.
Pharmaceutical compound
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
Eliminationhalf-life40.5 hours
Identifiers
  • 2-(4-chlorophenyl)-3-methyl-1,1-dioxo-1,3-thiazinan-4-one
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.001.190Edit this at Wikidata
Chemical and physical data
FormulaC11H12ClNO3S
Molar mass273.73 g·mol−1
3D model (JSmol)
  • O=S1(CCC(N(C)C1C2=CC=C(C=C2)Cl)=O)=O
  • InChI=1S/C11H12ClNO3S/c1-13-10(14)6-7-17(15,16)11(13)8-2-4-9(12)5-3-8/h2-5,11H,6-7H2,1H3 checkY
  • Key:WEQAYVWKMWHEJO-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Chlormezanone (marketed under thebrandnameTrancopal orFenaprim) is adrug used as ananxiolytic and amuscle relaxant.[1]

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

Synthesis

[edit]
Chlormezanone synthesis[3][4]

References

[edit]
  1. ^Turner P, Volan G, Wiseman H (1997).Drugs Handbook. UK: Palgrave Macmillan. p. 20.ISBN 978-1-349-13937-8.
  2. ^Lerch M, Mainetti C, Terziroli Beretta-Piccoli B, Harr T (February 2018). "Current Perspectives on Stevens-Johnson Syndrome and Toxic Epidermal Necrolysis".Clinical Reviews in Allergy & Immunology.54 (1):147–176.doi:10.1007/s12016-017-8654-z.PMID 29188475.S2CID 46796285.
  3. ^US 3082209, Surrey AR, "4-metathiazanone derivatives and their preparation", issued 1958, assigned to Sterling Drug Inc. 
  4. ^Surrey AR, Webb WG, Gesler RM (1958). "Central Nervous System Depressants. The Preparation of Some 2-Aryl-4-metathiazanones".Journal of the American Chemical Society.80 (13):3469–3471.Bibcode:1958JAChS..80.3469S.doi:10.1021/ja01546a065.

Further reading

[edit]
  • Wollina U, Hipler UC, Seeling A, Oelschlager H (2005). "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.doi:10.1159/000084910.PMID 15897685.S2CID 36642315.
  • Seeling A, Oelschläger H, Rothley D (April 2000). "[Important pharmaceutical-chemical characteristics of the central muscle relaxant chlormezanone]".Die Pharmazie.55 (4):293–296.PMID 10798243.
  • Oelschläger H, Klinger W, Rothley D, Seeling A, Bockhard H, Hofmann B, et al. (September 1998). "[Cleavage and biotransformation of the central muscle relaxant chlormezanone]".Die Pharmazie.53 (9):620–624.PMID 9770210.
  • Gautier V, Vinçon G, Demotes-Mainard F, Albin H (1990). "[Pharmacokinetics of chlormezanone in healthy volunteers]".Therapie.45 (4):315–319.PMID 2399514.
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