Chemistry:Trifluoperazine

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Short description: Typical antipsychotic medication
Trifluoperazine
Trifluoperazine.svg
Clinical data
Trade namesStelazine, Eskazinyl, Eskazine, Jatroneural, others
AHFS/Drugs.comMonograph
MedlinePlusa682121
Pregnancy
category
  • AU: C
  • US: C (Risk not ruled out)
Routes of
administration		By mouth, IM
Drug classTypical antipsychotic
ATC code
Legal status
Legal status
Pharmacokinetic data
MetabolismLiver
Elimination half-life10–20 hours
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
PDB ligand
Chemical and physical data
FormulaC21H24F3N3S
Molar mass407.50 g·mol−1
3D model (JSmol)
  (verify)

Trifluoperazine, marketed under the brand name Stelazine among others, is a typical antipsychotic primarily used to treat schizophrenia.[1] It may also be used short term in those with generalized anxiety disorder but is less preferred to benzodiazepines.[1] It is of the phenothiazine chemical class. It was approved for medical use in the United States in 1959.[2]

Medical uses

Schizophrenia

Trifluoperazine is an effective antipsychotic for people with schizophrenia condition.[3] There is low-quality evidence that trifluoperazine increases the chance of being improved when compared to placebo when people are followed up for 19 weeks.[3] There is low-quality evidence that trifluoperazine reduces the risk of relapse when compared with placebo when people are followed for 5 months.[3] As of 2014 there was no good evidence for a difference between trifluoperazine and placebo with respect to the risk of experiencing intensified symptoms over a 16-week period nor in reducing significant agitation or distress.[3]

There is no good evidence that trifluoperazine is more effective for schizophrenia than lower-potency antipsychotics like chlorpromazine, chlorprothixene, thioridazine and levomepromazine, but trifluoperazine appears to cause more adverse effects than these drugs.[4]

Other

It appears to be effective for people with generalized anxiety disorder but the benefit–risk ratio was unclear as of 2005.[5]

It has been experimentally used as a drug to kill eukaryotic pathogens in humans.[6]

Side effects

Its use in many parts of the world has declined because of highly frequent and severe early and late tardive dyskinesia, a type of extrapyramidal symptom. The annual development rate of tardive dyskinesia may be as high as 4%.[citation needed]

A 2004 meta-analysis of the studies on trifluoperazine found that it is more likely than placebo to cause extrapyramidal side effects such as akathisia, dystonia, and Parkinsonism.[7] It is also more likely to cause somnolence and anticholinergic side effects such as red eye and xerostomia (dry mouth).[7] All antipsychotics can cause the rare and sometimes fatal neuroleptic malignant syndrome.[8] Trifluoperazine can lower the seizure threshold.[9] The antimuscarinic action of trifluoperazine can cause excessive dilation of the pupils (mydriasis), which increases the chances of patients with hyperopia developing glaucoma.[10]

Contraindications

Trifluoperazine is contraindicated in CNS depression, coma, and blood dyscrasias. Trifluoperazine should be used with caution in patients suffering from renal or hepatic impairment.

Mechanism of action

Trifluoperazine has central antiadrenergic,[11] antidopaminergic,[12][13] and minimal anticholinergic effects.[14] It is believed to work by blockading dopamine D1 and D2 receptors in the mesocortical and mesolimbic pathways, relieving or minimizing such symptoms of schizophrenia as hallucinations, delusions, and disorganized thought and speech.[7] It also has antihistaminergic properties (H1 Ki = 17.5[15]).

Names

Brand names include Eskazinyl, Eskazine, Jatroneural, Modalina, Sizonil, Stelazine, Stilizan, Terfluzine, Trifluoperaz and Triftazin.

In the United Kingdom and some other countries, trifluoperazine is sold and marketed under the brand 'Stelazine'.

The drug is sold as tablet, liquid and 'Trifluoperazine-injectable USP' for deep intramuscular short-term use. GP studying pharmacological data has indicated cases of neck vertebrae irreversible fusing leading to NHS preparations being predominantly of the liquid form trifluoperazine as opposed to the tablet form as in Stela zine etc.

In the past, trifluoperazine was used in fixed combinations with the MAO inhibitor (antidepressant) tranylcypromine (tranylcypromine/trifluoperazine) to attenuate the strong stimulating effects of this antidepressant. This combination was sold under the brand name Jatrosom N, Stelapar, among others. Likewise a combination with amobarbital (potent sedative/hypnotic agent) for the amelioration of psychoneurosis and insomnia existed under the brand name Jalonac. In Italy the first combination remained available under the brand name Parmodalin (10 mg of tranylcypromine and 1 mg of trifluoperazine) until its discontinuation in 2019.

References

  1. ↑ 1.0 1.1 "Trifluoperazine Hydrochloride". The American Society of Health-System Pharmacists. https://www.drugs.com/monograph/trifluoperazine-hydrochloride.html. 
  2. ↑ "Trifluoperazine: A Sprightly Old Drug". Journal of Psychosocial Nursing and Mental Health Services 54 (1): 20–2. January 2016. doi:10.3928/02793695-20151223-01. PMID 26760133. 
  3. ↑ 3.0 3.1 3.2 3.3 "Trifluoperazine versus placebo for schizophrenia". The Cochrane Database of Systematic Reviews 1 (1): CD010226. January 2014. doi:10.1002/14651858.CD010226.pub2. PMID 24414883.  Wikiversity:Trifluoperazine versus placebo for schizophrenia § References
  4. ↑ "Trifluoperazine versus low-potency first-generation antipsychotic drugs for schizophrenia". The Cochrane Database of Systematic Reviews (7): CD009396. July 2014. doi:10.1002/14651858.CD009396.pub2. PMID 25003310. 
  5. ↑ "Evidence-based pharmacotherapy of Generalized Anxiety Disorder". The International Journal of Neuropsychopharmacology 8 (2): 293–302. June 2005. doi:10.1017/S1461145704004870. PMID 15576000. 
  6. ↑ "Successful treatment of Balamuthia amoebic encephalitis: presentation of 2 cases". Clinical Infectious Diseases 37 (10): 1304–1312. November 2003. doi:10.1086/379020. PMID 14583863. 
  7. ↑ 7.0 7.1 7.2 "Trifluoperazine for schizophrenia". Cochrane Database of Systematic Reviews 2004 (1): CD003545. 2004. doi:10.1002/14651858.CD003545.pub2. PMID 14974020. 
  8. ↑ "The neuroleptic malignant syndrome". Archives of Internal Medicine 142 (6): 1183–5. June 1982. doi:10.1001/archinte.142.6.1183. PMID 6124221. 
  9. ↑ "Antipsychotic medication and seizures: a review". Drugs of Today 39 (7): 551–7. July 2003. doi:10.1358/dot.2003.39.7.799445. PMID 12973403. 
  10. ↑ "Toxic effects of phenothiazines on the eye". Documenta Ophthalmologica. Advances in Ophthalmology 28 (1): 1–69. July 1970. doi:10.1007/BF00153873. PMID 5312274. 
  11. ↑ "Trifluoperazine and chlorpromazine antagonize alpha 1- but not alpha2- adrenergic effects". Molecular Pharmacology 23 (1): 67–70. January 1983. PMID 6135146. http://molpharm.aspetjournals.org/cgi/pmidlookup?view=long&pmid=6135146. Retrieved 2009-06-21. 
  12. ↑ "Antipsychotic drug doses and neuroleptic/dopamine receptors". Nature 261 (5562): 717–9. June 1976. doi:10.1038/261717a0. PMID 945467. Bibcode: 1976Natur.261..717S. 
  13. ↑ "Dopamine receptor binding predicts clinical and pharmacological potencies of antischizophrenic drugs". The Journal of Neuropsychiatry and Clinical Neurosciences 8 (2): 223–6. 1996. doi:10.1176/jnp.8.2.223. PMID 9081563. http://neuro.psychiatryonline.org/cgi/content/abstract/8/2/223. Retrieved 2009-06-21. 
  14. ↑ "Trifluoperazine Hydrochloride". CRC desk reference of clinical pharmacology (illustrated ed.). CRC Press. 1998. ISBN 978-0-8493-9683-0. https://books.google.com/books?id=-EAxShTKfGAC&q=trifluoperazine%20anticholinergic&pg=PA580. Retrieved 2009-06-21. 
  15. ↑ "Antagonism of central histamine H1 receptors by antipsychotic drugs". European Journal of Pharmacology 52 (3–4): 397–399. December 1978. doi:10.1016/0014-2999(78)90297-2. PMID 32056. 



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