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
| Molecular Formula | C11H12ClNO3S |
| Molecular Weight | 273.736 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
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 |
|---|---|---|
| Drug-related gustatory disorders. | 1978 Jan-Feb |
|
| [Drug-induced hepatitis with cholestasis following therapy with chlormezanone]. | 1985 Dec |
|
| [Pharmacokinetics of chlormezanone in healthy volunteers]. | 1990 Jul-Aug |
|
| Chlormezanone-induced fulminant hepatitis in a pregnant woman: successful delivery and liver transplantation. | 1992 May-Jun |
|
| [Cleavage and biotransformation of the central muscle relaxant chlormezanone]. | 1998 Sep |
|
| [Important pharmaceutical-chemical characteristics of the central muscle relaxant chlormezanone]. | 2000 Apr |
|
| [Lyell syndrome in Senegal: responsibility of thiacetazone]. | 2001 Dec |
|
| [Acute confusional syndrome associated to Chlormezanone use]. | 2002 Jun |
|
| [Retrospective of national pharmacovigilance surveys on drug-induced bullous, vesicular eruptions: methods and results ]. | 2002 May-Jun |
|
| [Acute confusional syndrome associated to chlormezanone]. | 2002 Nov |
|
| Risk of serious skin disorders among users of oral antifungals: a population-based study. | 2002 Nov 28 |
|
| [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 |
|
| Stimulatory effects of chlorzoxazone, a centrally acting muscle relaxant, on large conductance calcium-activated potassium channels in pituitary GH3 cells. | 2003 Jan 3 |
|
| Investigations of interactions of chlormezanone racemate and its enantiomers on human keratinocytes and human leucoytes in vitro. | 2005 May-Jun |
|
| Biology and therapy of fibromyalgia. New therapies in fibromyalgia. | 2006 |
|
| Adjuvant laser acupuncture in the treatment of whiplash injuries: a prospective, randomized placebo-controlled trial. | 2006 Mar |
|
| [Retrospective analysis of the combined therapy of terazosin with chlormezanone for chronic prostatitis/chronic pelvic pain syndrome]. | 2009 Aug |
|
| Fixed drug eruption resulting from fluconazole use: a case report. | 2009 Jul 6 |
|
| Anesthetic management for emergent Cesarean section in a patient with toxic epidermal necrolysis -A case report-. | 2010 Dec |
|
| Toxic epidermal necrolysis and Stevens-Johnson syndrome. | 2010 Dec 16 |
|
| Flupirtine in pain management: pharmacological properties and clinical use. | 2010 Oct |
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 Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 10:19:46 GMT 2023
by
admin
on
Sat Dec 16 10:19:46 GMT 2023
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| Record UNII |
C14WB33Y0S
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| Record Status |
Validated (UNII)
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| Record Version |
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-
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C14WB33Y0S
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102818-67-7
Created by
admin on Sat Dec 16 10:19:46 GMT 2023 , Edited by admin on Sat Dec 16 10:19:46 GMT 2023
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RACEMATE -> ENANTIOMER |
