Details
| 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
DescriptionSources: www.ncbi.nlm.nih.gov/mesh/68002720Curator's Comment: description was created based on several sources, including
http://www.who.int/medicines/publications/drugalerts/drug_alert53chlormezanone_serious_cutaneous_reactions.pdf |
https://www.drugbank.ca/drugs/DB01178
Sources: www.ncbi.nlm.nih.gov/mesh/68002720
Curator's Comment: description was created based on several sources, including
http://www.who.int/medicines/publications/drugalerts/drug_alert53chlormezanone_serious_cutaneous_reactions.pdf |
https://www.drugbank.ca/drugs/DB01178
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
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
4.62 mg/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2399514 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORMEZANONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
164.19 mg × h/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2399514 |
400 mg 1 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CHLORMEZANONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
224.93 mg × h/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2399514 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORMEZANONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
37.14 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2399514 |
400 mg 1 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CHLORMEZANONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
40.5 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2399514 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORMEZANONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
4 g single, oral Overdose Dose: 4 g Route: oral Route: single Dose: 4 g Co-administed with:: acetaminophen, p.o(18 g) Sources: Page: p.45 |
healthy, 46 n = 1 Health Status: healthy Age Group: 46 Sex: M Population Size: 1 Sources: Page: p.45 |
Disc. AE: Coma... AEs leading to discontinuation/dose reduction: Coma (grade 5) Sources: Page: p.45 |
400 mg 3 times / day multiple, oral Recommended Dose: 400 mg, 3 times / day Route: oral Route: multiple Dose: 400 mg, 3 times / day Sources: Page: p.44, p.45 |
unhealthy n = 10 Health Status: unhealthy Condition: Painful muscular spasms Population Size: 10 Sources: Page: p.44, p.45 |
Disc. AE: Muscular weakness, Ataxia... AEs leading to discontinuation/dose reduction: Muscular weakness Sources: Page: p.44, p.45Ataxia Stumbling Tachycardia |
800 mg single, oral Studied dose Dose: 800 mg Route: oral Route: single Dose: 800 mg Sources: Page: p.44 |
unhealthy n = 5 Health Status: unhealthy Condition: Painful muscular spasms Population Size: 5 Sources: Page: p.44 |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Coma | grade 5 Disc. AE |
4 g single, oral Overdose Dose: 4 g Route: oral Route: single Dose: 4 g Co-administed with:: acetaminophen, p.o(18 g) Sources: Page: p.45 |
healthy, 46 n = 1 Health Status: healthy Age Group: 46 Sex: M Population Size: 1 Sources: Page: p.45 |
| Ataxia | Disc. AE | 400 mg 3 times / day multiple, oral Recommended Dose: 400 mg, 3 times / day Route: oral Route: multiple Dose: 400 mg, 3 times / day Sources: Page: p.44, p.45 |
unhealthy n = 10 Health Status: unhealthy Condition: Painful muscular spasms Population Size: 10 Sources: Page: p.44, p.45 |
| Muscular weakness | Disc. AE | 400 mg 3 times / day multiple, oral Recommended Dose: 400 mg, 3 times / day Route: oral Route: multiple Dose: 400 mg, 3 times / day Sources: Page: p.44, p.45 |
unhealthy n = 10 Health Status: unhealthy Condition: Painful muscular spasms Population Size: 10 Sources: Page: p.44, p.45 |
| Stumbling | Disc. AE | 400 mg 3 times / day multiple, oral Recommended Dose: 400 mg, 3 times / day Route: oral Route: multiple Dose: 400 mg, 3 times / day Sources: Page: p.44, p.45 |
unhealthy n = 10 Health Status: unhealthy Condition: Painful muscular spasms Population Size: 10 Sources: Page: p.44, p.45 |
| Tachycardia | Disc. AE | 400 mg 3 times / day multiple, oral Recommended Dose: 400 mg, 3 times / day Route: oral Route: multiple Dose: 400 mg, 3 times / day Sources: Page: p.44, p.45 |
unhealthy n = 10 Health Status: unhealthy Condition: Painful muscular spasms Population Size: 10 Sources: Page: p.44, p.45 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Pharmacokinetics of chlormezanone in healthy volunteers]. | 1990 Jul-Aug |
|
| [Lyell syndrome in Senegal: responsibility of thiacetazone]. | 2001 Dec |
|
| [Acute confusional syndrome associated to Chlormezanone use]. | 2002 Jun |
|
| [New findings on the synthesis of the centrally acting muscle relaxant chlormezanone and its resolution of a gram scale using a Chiralcel OD column]. | 2003 Feb |
|
| Fixed drug eruption resulting from fluconazole use: a case report. | 2009 Jul 6 |
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.
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C14WB33Y0S
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102818-67-7
Created by
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SUBSTANCE RECORD
