- Molecular NameChlorprothixene
- SynonymAlpha-Chlorprothixene; Chloroprothixene; Chlorprothixen; Chlorprothixine; Chlorprotixen; Chlorprotixene; Chlorprotixine; Chlothixen; Cis-Chlorprothixene; CPT; CPX
- Weight315.868
- Drugbank_IDDB01239
- ACS_NO113-59-7
- Show 3D model
- LogP (experiment)5.654
- LogP (predicted, AB/LogP v2.0)5.18
- pka8.8
- LogD (pH=7, predicted)3.43
- Solubility (experiment)0.000295 mg/ml
- LogS (predicted, ACD/Labs)(ph=7)-3.08
- LogSw (predicted, AB/LogsW2.0)0.0
- Sw (mg/ml) (predicted, ACD/Labs)0.01
- No.of HBond Donors0
- No.of HBond Acceptors1
- No.of Rotatable Bonds3
- TPSA28.54
- StatusFDA approved
- Administrationoral (tablets, syrup, concentrate), intramuscular (seldom)
- PharmacologyA typical antipsychotic drug of the thioxanthene class. It has a low antipsychotic potency (half to 2/3 of chlorpromazine). Its principal indications are the treatment of psychotic disorders (e.g. schizophrenia) and of acute mania occurring as part of bipolar disorders.
- Absorption_valueN/A
- Absorption (description)Readily absorbed after oral administration
- Caco_2N/A
- Bioavailability41.0
- Protein bindingN/A
- Volume of distribution (VD)10 to 20 L/kg
- Blood/Plasma Partitioning ratio (D_blood)N/A
- MetabollsmUndergoes extensive first-pass metabolism. The major metabolite is the sulfoxide, but N-demethylation and N-oxidation also occur. Chlorprothixene and its sulfoxide metabolites are distributed into breast milk.
- Half life8~12 h
- ExcretionAfter daily oral doses, up to about 30% is excreted in the urine in 24 h as chlorprothixene sulfoxide, and up to about 40% is eliminated in the faeces also as the sulfoxide.
- Urinary ExcretionN/A
- Clerance17 ml/min/kg
- ToxicityThe estimated minimum lethal dose is 2.5 g, although recovery has occurred after the ingestion of 12 g. 2 to 12 h after a suicidal ingestion of about 10 g of chlorprothixene, a 31-year-old female had the following plasma concentrations: chlorprothixene 10 mg/L, desmethylchlorprothixene 8 mg/L, and chlorprothixene sulfoxide 1 mg/L. After 4 h haemoperfusion, the levels were: chlorprothixene 0.1 mg/L, desmethylchlorprothixene 0.1 mg/L, and chlorprothixene sulfoxide was not detected. [C. Koppel et al.,Intensive Care Med.,1987, 13, 358–360.] In 6 fatalities attributed to the ingestion of about 2.5 to 4 g of chlorprothixene, the following postmortem concentrations were reported: blood, chlorprothixene <0.1 to 0.4 mg/L, total metabolites <0.1 to 0.6 mg/L; liver, chlorprothixene 5 to 42 μg/g (mean 18), total metabolites 14 to 67 μg/g (mean 25); in 1 case a urine concentration of total thioxanthenes of 15 mg/L was also reported; desmethylchlorprothixene was the major metabolite in the liver. Alcohol was also detected in 3 cases. [H. Christensen,Acta Pharmacol. Toxicol.,1974, 34, 16–26.]
- LD50 (rat)N/A
- LD50 (mouse)N/A