Chlorpromazine

chemical compound

Chlorpromazine, also known by its trade name Thorazine, is an antipsychotic drug. It is typically used to treat Schizophrenia. It has also been used to treat bipolar disorder. It has been shown to help uncontrollable hiccups disappear. It is also used to help with nausea and vomiting.[2] Chlorpromazine was developed in 1950, making it the oldest antipsychotic drug.[3]

Chlorpromazine
Skeletal formula of chlorpromazine
Ball-and-stick model of the chlorpromazine molecule
Clinical data
Trade namesLargactil, Thorazine, many others
AHFS/Drugs.comMonograph
MedlinePlusa682040
License data
Pregnancy
category
  • AU: C
Routes of
administration
Oral (tablets and syrup available), rectal, IM, IV infusion
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability10–80% (Oral; large interindividual variation)[1]
Protein binding90–99%[1]
MetabolismLiver, mostly CYP2D6-mediated[1]
Elimination half-life30 hours
ExcretionUrine (43–65% in 24 hrs)[1]
Identifiers
  • 3-(2-chloro-10H-phenothiazin-10-yl)-N,N-dimethyl-propan-1-amine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard100.000.042 Edit this at Wikidata
Chemical and physical data
FormulaC17H19ClN2S
Molar mass318.86 g/mol (free base)
355.33 g/mol (hydrochloride)
3D model (JSmol)
  • CN(C)CCCN1c2ccccc2Sc3c1cc(cc3)Cl
  • 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 checkY
  • Key:ZPEIMTDSQAKGNT-UHFFFAOYSA-N checkY
  (verify)
An advert for Thorazine (which contains Chlorpromazine) from the 1960s.

References

change
  1. 1.0 1.1 1.2 1.3 "PRODUCT INFORMATION LARGACTIL" (PDF). TGA eBusiness Services. Sanofi Aventis Pty Ltd. 28 August 2012. Archived from the original on 30 March 2017. Retrieved 8 December 2013.
  2. "ChlorproMAZINE Monograph for Professionals". Drugs.com. Retrieved 2022-09-22.
  3. López-Muñoz, Francisco; Alamo, Cecilio; cuenca, Eduardo; Shen, Winston; Clervoy, Patrick; Rubio, Gabriel (2005-07-01). "History of the Discovery and Clinical Introduction of Chlorpromazine". Annals of Clinical Psychiatry. 17 (3): 113–135. doi:10.1080/10401230591002002. ISSN 1040-1237. PMID 16433053.