Chlorpromazine

Chlorpromazine (CPZ), marketed under the brand names Thorazine and Largactil among others, is an antipsychotic medication. It is primarily used to treat psychotic disorders such as schizophrenia. Other uses include the treatment of bipolar disorder, severe behavioral problems in children including those with attention deficit hyperactivity disorder, nausea and vomiting, anxiety before surgery, and hiccups that do not improve following other measures. It can be given orally (by mouth), by intramuscular injection (injection into a muscle), or intravenously (injection into a vein).

Not to be confused with Chlorpropamide.

Chlorpromazine
Clinical data
Trade namesLargactil, Thorazine, Sonazine, others
AHFS/Drugs.comMonograph
MedlinePlusa682040
License data
Pregnancy
category
  • AU: C
Routes of
administration		By mouth, rectal, intramuscular, intravenous
Drug classTypical antipsychotic
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C1 (Other controlled substances)
  • UK: POM (Prescription only)
  • US: WARNINGRx-only
  • EU: Rx-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability10–80% (Oral; large interindividual variation)
Protein binding90–99%
MetabolismLiver, mostly CYP2D6-mediated
Elimination half-life30 hours
ExcretionKidney (43–65% in 24 hrs)
Identifiers
  • 3-(2-chloro-10H-phenothiazin-10-yl)-N,N-dimethylpropan-1-amine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.042
Chemical and physical data
FormulaC17H19ClN2S
Molar mass318.86 g·mol−1
3D model (JSmol)
SMILES
  • CN(C)CCCN1c2ccccc2Sc2ccc(Cl)cc21
  • InChI=1S/C17H19ClN2S/c1-19(2)10-5-11-20-14-6-3-4-7-16(14)21-17-9-8-13(18)12-15(17)20/h3-4,6-9,12H,5,10-11H2,1-2H3 Y
  • Key:ZPEIMTDSQAKGNT-UHFFFAOYSA-N Y
  (verify)

Chlorpromazine is in the typical antipsychotic class, and, chemically, is one of the phenothiazines. Its mechanism of action is not entirely clear but believed to be related to its ability as a dopamine antagonist. It also has anti-serotonergic and antihistaminergic properties.

Common side effects include movement problems, sleepiness, dry mouth, low blood pressure upon standing, and increased weight. Serious side effects may include the potentially permanent movement disorder tardive dyskinesia, neuroleptic malignant syndrome, severe lowering of the seizure threshold, and low white blood cell levels. In older people with psychosis as a result of dementia it may increase the risk of death. It is unclear if it is safe for use in pregnancy.

Chlorpromazine was developed in 1950 and was the first antipsychotic on the market. It is on the World Health Organization's List of Essential Medicines. Its introduction has been labeled as one of the great advances in the history of psychiatry. It is available as a generic medication.

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