Chlormezanone

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Chlormezanone
Skeletal formula of chlormezanone
Space-filling model of the chlormezanone molecule
Systematic (IUPAC) name
2-(4-chlorophenyl)-3-methyl-1,1-dioxo-1,3-thiazinan-4-one
Clinical data
AHFS/Drugs.com International Drug Names
Legal status
  • ℞ (Prescription only)
Routes of
administration
Oral
Pharmacokinetic data
Biological half-life 40.5 hours
Identifiers
CAS Number 80-77-3 YesY
ATC code M03BB02 (WHO)
PubChem CID: 2717
IUPHAR/BPS 7323
DrugBank DB01178 YesY
ChemSpider 2616 YesY
UNII GP568V9G19 YesY
KEGG D00268 YesY
ChEBI CHEBI:3619 YesY
ChEMBL CHEMBL1200714 N
Chemical data
Formula C11H12ClNO3S
Molecular mass 273.737 g/mol
  • 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 YesY
  • Key:WEQAYVWKMWHEJO-UHFFFAOYSA-N YesY
 NYesY (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.

Chemistry

Chlormezanone synthesis.png

  • Sterling Drug Inc., US 3082209  (1958).
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References

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