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Chlormezanone


Chlormezanone
Systematic (IUPAC) name
2-(4-chlorophenyl)-3-methyl-1, 1-dioxo-1,3-thiazinan-4-one
Identifiers
CAS number	80-77-3
ATC code	M03BB02
PubChem	2717
DrugBank	APRD00865
Chemical data
Formula	C₁₁H₁₂Cl N O₃S
Mol. mass	273.737 g/mol
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	40.5 hr.
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status	℞-only(US) Withdrawn
Routes	Oral

Chlormezanone (marketed under the brand name Trancopal) is a drug used as an anxiolytic and a muscle relaxant.

It was discontinued worldwide in 1996 by its manufacturer, due to rare but serious cases of toxic epidermal necrolysis.

References

Wollina U, Hipler U, Seeling A, Oelschlager H. "Investigations of interactions of chlormezanone racemate and its enantiomers on human keratinocytes and human leucoytes in vitro.". Skin Pharmacol Physiol 18 (3): 132-8. PMID 15897685.
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.

v • d • e Muscle relaxants (M03)
Peripherally acting (primarily antinicotinic, neuromuscular-blocking drugs)	curare alkaloids (Alcuronium, Dimethyltubocurarine, Tubocurarine) - choline derivatives (Suxamethonium) - other quaternary ammonium compounds (Atracurium, Cisatracurium, Doxacurium chloride, Fazadinium bromide, Gallamine, Hexafluronium, Mivacurium chloride, Pancuronium, Pipecuronium bromide, Rocuronium bromide, Vecuronium) - other (Botulinum toxin)
Centrally acting	carbamic acid esters (Phenprobamate, Carisoprodol, Methocarbamol, Styramate, Febarbamate), Baclofen, Chlormezanone, Chlorzoxazone, Cyclobenzaprine, Lorazepam, Mephenesin, Orphenadrine, Phenyramidol, Pridinol, Tetrazepam, Thiocolchicoside, Tizanidine, Tolperisone
Directly acting	Dantrolene