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Chlorpromazine information


Chlorpromazine
Skeletal formula of chlorpromazine
Ball-and-stick model of the chlorpromazine molecule
Clinical data
Trade namesLargactil, Thorazine, Sonazine, others
AHFS/Drugs.comMonograph
MedlinePlusa682040
License data
  • US DailyMed: Chlorpromazine
Pregnancy
category
  • AU: C[1]
Routes of
administration
By mouth, rectal, intramuscular, intravenous
Drug classTypical antipsychotic
ATC code
  • N05AA01 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C1 (Other controlled substances)[3]
  • UK: POM (Prescription only)
  • US: WARNING[2]Rx-only
  • EU: Rx-only[4]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability10–80% (Oral; large interindividual variation)[5]
Protein binding90–99%[5]
MetabolismLiver, mostly CYP2D6-mediated[5]
Elimination half-life30 hours[6]
ExcretionKidney (43–65% in 24 hrs)[5]
Identifiers
IUPAC name
  • 3-(2-chloro-10H-phenothiazin-10-yl)-N,N-dimethylpropan-1-amine
CAS Number
  • 50-53-3 checkY (free base)
    69-09-0 (hydrochloride)
PubChem CID
  • 2726
IUPHAR/BPS
  • 83
DrugBank
  • DB00477 checkY
ChemSpider
  • 2625 checkY
UNII
  • U42B7VYA4P
KEGG
  • D00270 checkY
  • as HCl: D00789 checkY
ChEBI
  • CHEBI:3647 checkY
ChEMBL
  • ChEMBL71 checkY
CompTox Dashboard (EPA)
  • DTXSID0022808 Edit this at Wikidata
ECHA InfoCard100.000.042 Edit this at Wikidata
Chemical and physical data
FormulaC17H19ClN2S
Molar mass318.86 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • CN(C)CCCN1c2ccccc2Sc2ccc(Cl)cc21
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 checkY
  • Key:ZPEIMTDSQAKGNT-UHFFFAOYSA-N checkY
  (verify)

Chlorpromazine (CPZ), marketed under the brand names Thorazine and Largactil among others, is an antipsychotic medication.[6] It is primarily used to treat psychotic disorders such as schizophrenia.[6] 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.[6] It can be given orally (by mouth), by intramuscular injection (injection into a muscle), or intravenously (injection into a vein).[6]

Chlorpromazine is in the typical antipsychotic class,[6] 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.[6] It also has anti-serotonergic and antihistaminergic properties.[6]

Common side effects include movement problems, sleepiness, dry mouth, low blood pressure upon standing, and increased weight.[6] 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.[6] In older people with psychosis as a result of dementia it may increase the risk of death.[6] It is unclear if it is safe for use in pregnancy.[6]

Chlorpromazine was developed in 1950 and was the first antipsychotic on the market.[7][8] It is on the World Health Organization's List of Essential Medicines.[9][10] Its introduction has been labeled as one of the great advances in the history of psychiatry.[11][12] It is available as a generic medication.[6]

  1. ^ "Chlorpromazine Pregnancy and Breastfeeding Warnings". Drugs.com. 5 February 2020. Retrieved 21 August 2020.
  2. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  3. ^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.
  4. ^ "List of nationally authorised medicinal products - Active substance: chlorpromazine : Procedure no.: PSUSA/00000715/202005" (PDF). Ema.europa.eu. Retrieved 3 March 2022.
  5. ^ a b c d "Australian Product Information – Largactil (chlorpromazine hydrochloride)" (PDF). Therapeutic Goods Administration (TGA). Sanofi Aventis Pty Ltd. 28 August 2012. Archived from the original on 30 March 2017. Retrieved 8 December 2013.
  6. ^ a b c d e f g h i j k l m "Chlorpromazine Hydrochloride". The American Society of Health-System Pharmacists. Archived from the original on 8 December 2015. Retrieved 1 December 2015.
  7. ^ López-Muñoz F, Alamo C, Cuenca E, Shen WW, Clervoy P, Rubio G (2005). "History of the discovery and clinical introduction of chlorpromazine". Annals of Clinical Psychiatry. 17 (3): 113–135. doi:10.1080/10401230591002002. PMID 16433053.
  8. ^ Ban TA (August 2007). "Fifty years chlorpromazine: a historical perspective". Neuropsychiatric Disease and Treatment. 3 (4): 495–500. PMC 2655089. PMID 19300578.
  9. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  10. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  11. ^ López-Muñoz F, Alamo C, Cuenca E, Shen WW, Clervoy P, Rubio G (2005). "History of the discovery and clinical introduction of chlorpromazine". Annals of Clinical Psychiatry. 17 (3): 113–135. doi:10.1080/10401230591002002. PMID 16433053.
  12. ^ Shorter E (2005). A historical dictionary of psychiatry. New York: Oxford University Press. p. 6. ISBN 9780198039235. Archived from the original on 14 February 2017.

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Chlorpromazine

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Chlorpromazine (CPZ), marketed under the brand names Thorazine and Largactil among others, is an antipsychotic medication. It is primarily used to treat...

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List of adverse effects of chlorpromazine

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Chlorpromazine includes the following list of adverse effects (serious adverse effects appear in bold): Sedation (cf. "Thorazine shuffle" – a shuffling...

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Henri Laborit

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philosopher. In 1952, Laborit was instrumental in the development of the drug chlorpromazine, published his findings, and convinced three psychiatrists to test it...

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Typical antipsychotic

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antipsychotics to come into medical use were the phenothiazines, namely chlorpromazine which was discovered serendipitously. Another prominent grouping of...

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Perphenazine

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clinical use for decades. Perphenazine is roughly ten times as potent as chlorpromazine at the dopamine-2 (D2) receptor; thus perphenazine is considered a medium-potency...

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Antipsychotic

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syndromes include VMAT2 inhibitors. First-generation antipsychotics (e.g., chlorpromazine), known as typical antipsychotics, were first introduced in the 1950s...

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Reserpine

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schizophrenia, reserpine and chlorpromazine had similar rates of adverse effects, but that reserpine was less effective than chlorpromazine for improving a person's...

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Phenothiazine

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bioactive and have widespread use and rich history. The derivatives chlorpromazine and promethazine revolutionized the fields of psychiatry and allergy...

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Dissociative

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MS; Loiselle, RH; Giannini, MC (1984). "Comparison of haloperidol and chlorpromazine in the treatment of phencyclidine psychosis". Journal of Clinical Pharmacology...

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Psychopharmacology revolution

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discovery and it has been referred to as a "golden era". The history of chlorpromazine can be traced back to the work of BASF who were creating dyes at around...

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opioid analgesics Propranolol is the prototype of the beta blockers Chlorpromazine is the prototypical phenothiazine antipsychotic Imipramine is the prototypical...

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that experience a significant first-pass effect are buprenorphine, chlorpromazine, cimetidine, diazepam, ethanol (drinking alcohol), imipramine, insulin...

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doxepin, imipramine, trimipramine) Trimazosin Typical antipsychotics (e.g., chlorpromazine, fluphenazine, loxapine, thioridazine) Urapidil WB-4101 Zolertine...

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Lunatic asylum

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the first effective psychiatric drugs. The first anti-psychotic drug, chlorpromazine (known under the trade name Largactil in Europe and Thorazine in the...

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Clozapine

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Group Study #30 in which clozapine showed marked benefits compared to chlorpromazine in a group of patients with protracted psychosis and who had already...

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Acepromazine

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on animals as a sedative and antiemetic. A closely related analogue, chlorpromazine, is still used in humans. The standard pharmaceutical preparation, acepromazine...

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Promethazine

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diphenhydramine; the same line on medical chemistry led to the creation of chlorpromazine. As of July 2017, it is marketed under many brand names worldwide: Allersoothe...

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Prochlorperazine

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effects by blocking dopamine receptors. Prochlorperazine is analogous to chlorpromazine; both of these agents antagonize dopaminergic D2 receptors in various...

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Bupropion

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antidepressants (e.g., amitriptyline) Typical antipsychotics (e.g., chlorpromazine, fluphenazine, haloperidol, loxapine, perphenazine, pimozide, pipamperone...

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Fentanyl

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Brompton cocktail

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highly-pure ethyl alcohol (some recipes specify gin), and sometimes with chlorpromazine (Thorazine) to counteract nausea, it was given to terminally-ill individuals...

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Examples of compounds often cited as "dirty drugs" include tramadol, chlorpromazine, olanzapine, dextromethorphan, ibogaine, and ethanol, all of which bind...

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most potent commonly used antipsychotic (200 times more potent than chlorpromazine) Lumateperone, an atypical antipsychotic used for schizophrenia and...

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Jean Delay

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française (Chair 17). His assistant Pierre Deniker conducted a test of chlorpromazine on the male mental ward where Delay worked, and the two published their...

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human rights abuse. In the mid-1950s the first typical antipsychotic, chlorpromazine, was introduced, followed in the 1970s by the first atypical antipsychotic...

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