- Molecular NameChlormezanone
- SynonymChlormethazanone; Chlormethazone; Chlormezanon; Chlormezanone [BAN:INN:JAN]; Chlormezanonum [INN-Latin]; Clormetazanone; Clormetazon; Clormezanona [INN-Spanish]; Clormezanone [DCIT]; Dichloromethazanone; Dichloromezanone; dl-Chlormezanone…
- Weight273.74
- Drugbank_IDDB01178
- ACS_NO80-77-3
- Show 3D model
- LogP (experiment)1.208
- LogP (predicted, AB/LogP v2.0)0.64
- pkaN/A
- LogD (pH=7, predicted)0.64
- Solubility (experiment)2.5 mg/ml
- LogS (predicted, ACD/Labs)(ph=7)-3.36
- LogSw (predicted, AB/LogsW2.0)1.96
- Sw (mg/ml) (predicted, ACD/Labs)0.12
- No.of HBond Donors0
- No.of HBond Acceptors4
- No.of Rotatable Bonds1
- TPSA62.83
- StatusFDA approved
- AdministrationN/A
- PharmacologyA drug used as an anxiolytic and a muscle relaxant.
- Absorption_valueN/A
- Absorption (description)Rapidly absorbed after oral administration, with peak plasma concentrations reached after 1 to 2 h.
- Caco_2N/A
- Bioavailability100.0
- Protein binding50.0
- Volume of distribution (VD)N/A
- Blood/Plasma Partitioning ratio (D_blood)N/A
- MetabollsmIt appears to be metabolised by hydrolysis then oxidation to chlorobenzaldehyde and conjugation.
- Half life20~30 h
- ExcretionLess than 5% of a dose is excreted in the urine as unchanged drug in 48 h; about 40% of a dose is excreted in the urine in 72 h as acidic metabolites, mainly 4-chlorohippuric acid.
- Urinary ExcretionN/A
- CleranceN/A
- ToxicityChlormezanone has been withdrawn from the market in many countries because of reports of serious skin reactions. A 39-year-old woman was found in a comatose state 6 h after ingesting chlormezanone (possibly up to 12 g). A liver biopsy revealed diffuse hydropic degeneration and necrosis of hepatocytes. Chlormezanone levels 7 to 8 h post ingestion and then every other day were as follows: 78.0, 45.9, 21.6 and 7.8 mg/L in serum and 3.8, 1.1, 0.5 mg/L then untraceable, in urine. [B. S. Sheu et al.,Am. J. Gastroenterol.,1995, 90, 833–835.] In a fatality due to the combined ingestion of chlormezanone (possibly up to 11 g), diazepam (up to 200 mg) and nitrazepam (up to 80 mg), the following postmortem concentrations of chlormezanone were reported: femoral blood, 53 mg/L; brain 109 μg/g; liver, 88 μg/g and urine, 31 mg/L. [C. Koppel et al.,Eur. J. Drug Metab. Pharmacokinet.,1991, 16, 43–47.] Symptoms of overdose include drowsiness, weakness, nausea, dizziness, abdominal pain, cerebral oedema and renal tubular necrosis, hyperglycaemia and hypoglycaemia, liver damage, encephalopathy, coma and death.
- LD50 (rat)LD50=1450
- LD50 (mouse)N/A