Largactil

Chlorpromazine
Clinical data


Trade names	Largactil, Thorazine, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682040
License data	US FDA: Chlorpromazine
Pregnancy category	AU: C US: C (Risk not ruled out)
Routes of administration	Oral (tablets and syrup available), rectal, IM, IV infusion
ATC code	N05AA01 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	10–80% (Oral; large interindividual variation)
Protein binding	90–99%
Metabolism	Liver, mostly CYP2D6-mediated
Biological half-life	30 hours
Excretion	Urine (43–65% in 24 hrs)
Identifiers
IUPAC name 3-(2-chloro-10H-phenothiazin-10-yl)-N,N-dimethyl-propan-1-amine
CAS Number	50-53-3^Y
PubChem CID	2726
IUPHAR/BPS	83
DrugBank	DB00477^Y
ChemSpider	2625^Y
UNII	U42B7VYA4P
KEGG	D00270^Y
ChEBI	CHEBI:3647^Y
ChEMBL	CHEMBL71^Y
ECHA InfoCard	100.000.042
Chemical and physical data
Formula	C₁₇H₁₉ClN₂S
Molar mass	318.86 g/mol (free base) 355.33 g/mol (hydrochloride)
3D model (Jmol)	Interactive image
SMILES CN(C)CCCN1c2ccccc2Sc3c1cc(cc3)Cl
InChI 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

Chlorpromazine (CPZ), marketed under the trade 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, attention deficit hyperactivity disorder, nausea and vomiting, anxiety before surgery, and hiccups that do not improve following other measures. It can be given by mouth, by injection into a muscle, or into a vein.

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, and low white blood cell levels. In older people with psychosis as a result of dementia it may increase the risk of dying. It is unclear if it is safe for use in pregnancy. Chlorpromazine is in the typical antipsychotic class. 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.