[Important pharmaceutical-chemical characteristics of the central muscle relaxant chlormezanone].
The enantinomers of chlormezanone (1) may be achieved by enantioselective HPLC separation with a yield of 98% using a OD-Daicel column. Both enantiomers bind to human serum albumin (HSA) at pH 7.4 to a range of 11-12%. Binding to the globuline fractions is much less (2-4%, equilibrium dialysis, validation by ultrafiltration). It could be demonstrated by means of 1H-NMR spectroscopy that 1 binds to HSA with the benzene ring as well as with the thiazanone ring. The velocity of racemization could be measured for the first time using a BSA column. The enantiomers undergo racemization at pH 7.4 and 37 degrees C with a halflife of approx. 20.5 h.
Seeling
A
A
Institut für Pharmazie, Friedrich-Schiller-Universität, Jena, Germany.
Oelschläger
H
H
Rothley
D
D
D002720:Chlormezanone / Q000737:chemistry* / Q000494:pharmacology*; D002851:Chromatography, High Pressure Liquid; D003956:Dialysis; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D009125:Muscle Relaxants, Central / Q000737:chemistry* / Q000494:pharmacology*; D011485:Protein Binding; D012709:Serum Albumin / Q000378:metabolism; D013237:Stereoisomerism; D014462:Ultrafiltration
D009125:Muscle Relaxants, Central; D012709:Serum Albumin; D002720:Chlormezanone