Chlormezanone

Last updated
Chlormezanone
Chlormezanone.svg
Chlormezanone-3D-spacefill.png
Clinical data
AHFS/Drugs.com International Drug Names
Routes of
administration
Oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Elimination half-life 40.5 hours
Identifiers
  • 2-(4-chlorophenyl)-3-methyl-1,1-dioxo-1,3-thiazinan-4-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.001.190 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C11H12ClNO3S
Molar mass 273.73 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 Yes check.svgY
  • Key:WEQAYVWKMWHEJO-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Chlormezanone (marketed under the brandname Trancopal or Fenaprim) is a drug used as an anxiolytic and a muscle relaxant. [1]

Contents

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

Synthesis

Chlormezanone synthesis Synthesis of chlormezanone.svg
Chlormezanone synthesis

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References

  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. doi:10.1021/ja01546a065.

Further reading