| Stereochemistry | UNKNOWN |
| Molecular Formula | C11H12ClNO3S |
| Molecular Weight | 273.736 |
| Optical Activity | ( + ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1C(C2=CC=C(Cl)C=C2)S(=O)(=O)CCC1=O
InChI
InChIKey=WEQAYVWKMWHEJO-UHFFFAOYSA-N
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
Chlormezanone (TRANCOPAL®) is a non-benzodiazepine that is used in the management of anxiety. It has been suggested for use in the treatment of muscle spasm. It binds to central benzodiazepine receptors which interact allosterically with GABA receptors. This potentiates the effects of the inhibitory neurotransmitter GABA, increasing the inhibition of the ascending reticular activating system and blocking the cortical and limbic arousal that occurs following stimulation of the reticular pathways. Chlormezanone (TRANCOPAL®) was discontinued worldwide in 1996 by Sanofi due to confirmed serious and rare cutaneous reactions (toxic epidermal necrolysis also known as Stevens-Johnson syndrome).
CNS Activity
Originator
Approval Year
Doses
AEs
Sourcing
PubMed
Patents
Sample Use Guides
The investigation was performed in order to investigate whether the racemic chlormezanone and both enantiomers differ in their potential cytotoxicty for human HaCaT keratinocytes. In the dosage range of 0.001 to 0.1 mg/ml chlormezanone, no antiproliferative effects were measured with the racemate and both enantiomers. At 1.0 mg/ml, a decrease of proliferative activity was seen after 48 h incubation time of about 50% for the enantiomers and of about 80% for the racemate (PicoGreen assay) and 50% (enantiomers) or 21% (racemate) in the ATP assay, respectively. Oxygen radicals production by human interleukin-3-stimulated leukocytes was significantly inhibited at concentrations < or =0.01 mg/ml by the racemate and the (+)-enantiomer, whereas the (-)-enantiomer was less effective.
SUBSTANCE RECORD
