chlormezanone

Trade name: trancopal

Small moleculeapproved

Approved

May 20, 1960

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). — NCATS

Clinical trial activity

0 trials · 0 clinical orgs · 1 marketing orgs

Phase 1

Phase 2

Phase 3

Phase 4

Timeline

1960s

May 20, 1960
Sanofi-Aventis — Earliest FDA Approval
May 20, 1960
Sanofi-Aventis — NDA Secondary Org
May 20, 1960
Sanofi-Aventis — NDA Organization

Indications

Approved for

Anxiety (approved 1960)

Mechanism of action

Unspecified targetOTHER
Unknown
Mode of action not fully understood; it seems to act as a muscle relaxant by interfering with GABA A receptors, sodium channels and calcium channels

Approval history

approvedMay 20, 1960

Chemistry & pharmacology

Loading structure…

SMILES

CN1C(C2=CC=C(Cl)C=C2)S(=O)(=O)CCC1=O

Mol. weight: 273.736 g/mol
Lipinski Ro5: Pass
Rule of 3: Yes
Chirality: Racemic Mixture
Inorganic: No
Polymer: No
Delivery: Oral

Oral

Yes

Parenteral

Topical

Sources

Also known as

2-(p-chlorophenyl)tetrahydro-3-methyl-4h-1,3-thiazin-4-one 1,1-dioxide
2-(p-chlorophenyl)tetrahydro-3-methyl-4h-1,3-thiazin-4-one 1,1-dioxide
2-(p-chlorphenyl)-3-methyl-1,3-perhydrothiazin-4-on-1,1-dioxide
2-(p-chlorphenyl)-3-methyl-1,3-perhydrothiazin-4-on-1,1-dioxide
chlormethazanone
chlormethazanone
chlormethazanone
chlormethazanone
chlormethazone
chlormezanona
chlormezanona
chlormezanone
chlormezanone
chlormezanone
chlormezanone
chlormezanone
chlormezanone
chlormezanone
chlormezanone
chlormezanone
chlormezanone
(+-)-chlormezanone
(+-)-chlormezanone
(±)-chlormezanone
(±)-chlormezanone
chlormezanonum
chlormezanonum
clormezanona
clormezanona
clormezanone
clormezanone
clormezanone
clormezanone
clormezanone
clormezanone
dichloromezanone
dl-chlormezanone
lyseen new
phenarol
trancopal
trancopal

Organizations

Marketing (2)

Organization	Org type	Relationship	Date
Sanofi-Aventis	For profit	NDA2	May 20, 1960
Sanofi-Aventis	For profit	NDA	May 20, 1960