Chlormezanone

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

Chlormezanone

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	M03BB02 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Elimination half-life	40.5 hours
Identifiers
IUPAC name 2-(4-chlorophenyl)-3-methyl-1,1-dioxo-1,3-thiazinan-4-one
CAS Number	80-77-3
PubChem CID	2717
IUPHAR/BPS	7323
DrugBank	DB01178
ChemSpider	2616
UNII	GP568V9G19
KEGG	D00268
ChEBI	CHEBI:3619
ChEMBL	ChEMBL1200714
CompTox Dashboard (EPA)	DTXSID3022798
ECHA InfoCard	100.001.190
Chemical and physical data
Formula	C11H12ClNO3S
Molar mass	273.73 g·mol^−1
3D model (JSmol)	Interactive image
SMILES O=S1(CCC(N(C)C1C2=CC=C(C=C2)Cl)=O)=O
InChI 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 Key:WEQAYVWKMWHEJO-UHFFFAOYSA-N
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Its use was discontinued in many countries from 1996 on, due to rare but serious cases of toxic epidermal necrolysis.

Synthesis

Chlormezanone synthesis

• 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.

References

• 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. S2CID 36642315.
• 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.