Zuclopenthixol

Last updated
Zuclopenthixol
Zuclopenthixol.svg
Clinical data
Trade names Clopixol
AHFS/Drugs.com International Drug Names
Pregnancy
category
  • AU:C
Routes of
administration 		Oral, IM
Drug class Typical antipsychotic
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only) [1]
  • BR: Class C1 (Other controlled substances) [2]
  • UK: POM (Prescription only)
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability 49% (oral)
Protein binding 98%
Metabolism Liver (CYP2D6 and CYP3A4-mediated)
Elimination half-life 20 hours (oral), 19 days (IM)
Excretion Feces
Identifiers
  • cis-(Z)-2-(4-(3-(2-chloro-9H-thioxanthen-9-ylidene)propyl)piperazin-1-yl)ethanol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.053.398 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C22H25ClN2OS
Molar mass 400.97 g·mol−1
3D model (JSmol)
  • Clc2cc1C(\c3c(Sc1cc2)cccc3)=C/CCN4CCN(CCO)CC4
  • InChI=1S/C22H25ClN2OS/c23-17-7-8-22-20(16-17)18(19-4-1-2-6-21(19)27-22)5-3-9-24-10-12-25(13-11-24)14-15-26/h1-2,4-8,16,26H,3,9-15H2/b18-5- Yes check.svgY
  • Key:WFPIAZLQTJBIFN-DVZOWYKESA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Zuclopenthixol (brand names Cisordinol, Clopixol and others), also known as zuclopentixol, is a medication used to treat schizophrenia and other psychoses. It is classed, pharmacologically, as a typical antipsychotic. Chemically it is a thioxanthene. It is the cis -isomer of clopenthixol (Sordinol, Ciatyl). [3] Clopenthixol was introduced in 1961, while zuclopenthixol was introduced in 1978.[ citation needed ]

Contents

Zuclopenthixol is a D1 and D2 antagonist, α1-adrenergic and 5-HT2 antagonist. [4] While it is approved for use in Australia, Canada, Ireland, India, New Zealand, Singapore, South Africa and the UK, it is not approved for use in the United States. [5] [6]

Medical uses

Available forms

Zuclopenthixol is available in three major preparations:

It is also used in the treatment of acute bipolar mania.

Dosing

As a long-acting injection, zuclopenthixol decanoate comes in a 200 mg and 500 mg ampoule. Doses can vary from 50 mg weekly to the maximum licensed dose of 600 mg weekly. In general, the lowest effective dose to prevent relapse is preferred. The interval may be shorter as a patient starts on the medication before extending to 3 weekly intervals subsequently. The dose should be reviewed and reduced if side effects occur, though in the short-term an anticholinergic medication benztropine may be helpful for tremor and stiffness, while diazepam may be helpful for akathisia. 100 mg of zuclopenthixol decanoate is roughly equivalent to 20 mg of flupentixol decanoate or 12.5 mg of fluphenazine decanoate.

In oral form zuclopenthixol is available in 2, 10, 25 and 40 mg tablets, with a dose range of 20–60 mg daily. [11]

Side effects

Chronic administration of zuclopenthixol (30 mg/kg/day for two years) in rats resulted in small, but significant, increases in the incidence of thyroid parafollicular carcinomas and, in females, of mammary adenocarcinomas and of pancreatic islet cell adenomas and carcinomas. An increase in the incidence of mammary adenocarcinomas is a common finding for D2 antagonists which increase prolactin secretion when administered to rats. An increase in the incidence of pancreatic islet cell tumours has been observed for some other D2 antagonists. The physiological differences between rats and humans with regard to prolactin make the clinical significance of these findings unclear.

Withdrawal syndrome: Abrupt cessation of therapy may cause acute withdrawal symptoms (eg, nausea, vomiting, or insomnia). Symptoms usually begin in 1 to 4 days of withdrawal and subside within 1 to 2 weeks. [12] [13]

Other permanent side effects are similar to many other typical antipsychotics, namely extrapyramidal symptoms as a result of dopamine blockade in subcortical areas of the brain. This may result in symptoms similar to those seen in Parkinson's disease and include a restlessness and inability to sit still known as akathisia, a slow tremor and stiffness of the limbs. [10] Zuclopenthixol is thought to be more sedating than the related flupentixol, though possibly less likely to induce extrapyramidal symptoms than other typical depots. [7] As with other dopamine antagonists, zuclopenthixol may sometimes elevate prolactin levels; this may occasionally result in amenorrhoea or galactorrhoea in severe cases. Neuroleptic malignant syndrome is a rare but potentially fatal side effect. Any unexpected deterioration in mental state with confusion and muscle stiffness should be seen by a physician.

Zuclopenthixol decanoate induces a transient dose-dependent sedation. However, if the patient is switched to maintenance treatment with zuclopenthixol decanoate from oral zuclopenthixol or from i.m. zuclopenthixol acetate the sedation will be no problem. Tolerance to the unspecific sedative effect develops rapidly. [14]

Very common Adverse Effects (≥10% incidence) [15]
Common (1–10%) [15]
Uncommon (0.1–1%) [15]
Rare (0.01–0.1%) [15]
Very rare (<0.01%) [15]

Pharmacology

Pharmacodynamics

Cisordinol 10 mg tablet Cisordinol.jpg
Cisordinol 10 mg tablet

Zuclopenthixol antagonises both dopamine D1 and D2 receptors, α1-adrenoceptors and 5-HT2 receptors with a high affinity, but has no affinity for muscarinic acetylcholine receptors. It weakly antagonises the histamine (H1) receptor but has no α2-adrenoceptor blocking activity [ citation needed ].

Evidence from in vitro work and clinical sources (i.e. therapeutic drug monitoring databases) suggests that both CYP2D6 and CYP3A4 play important roles in zuclopenthixol metabolism. [16]

Pharmacokinetics

Pharmacokinetics of long-acting injectable antipsychotics
MedicationBrand nameClassVehicleDosageTmaxt1/2 singlet1/2 multiplelogPcRef
Aripiprazole lauroxil Aristada Atypical Water a441–1064 mg/4–8 weeks24–35 days ?54–57 days7.9–10.0
Aripiprazole monohydrate Abilify Maintena Atypical Water a300–400 mg/4 weeks7 days ?30–47 days4.9–5.2
Bromperidol decanoate Impromen Decanoas Typical Sesame oil 40–300 mg/4 weeks3–9 days ?21–25 days7.9 [17]
Clopentixol decanoate Sordinol Depot Typical Viscoleo b50–600 mg/1–4 weeks4–7 days ?19 days9.0 [18]
Flupentixol decanoate Depixol Typical Viscoleo b10–200 mg/2–4 weeks4–10 days8 days17 days7.2–9.2 [18] [19]
Fluphenazine decanoate Prolixin Decanoate Typical Sesame oil 12.5–100 mg/2–5 weeks1–2 days1–10 days14–100 days7.2–9.0 [20] [21] [22]
Fluphenazine enanthate Prolixin Enanthate Typical Sesame oil 12.5–100 mg/1–4 weeks2–3 days4 days ?6.4–7.4 [21]
Fluspirilene Imap, Redeptin Typical Water a2–12 mg/1 week1–8 days7 days ?5.2–5.8 [23]
Haloperidol decanoate Haldol Decanoate Typical Sesame oil 20–400 mg/2–4 weeks3–9 days18–21 days7.2–7.9 [24] [25]
Olanzapine pamoate Zyprexa Relprevv Atypical Water a150–405 mg/2–4 weeks7 days ?30 days–
Oxyprothepin decanoate Meclopin Typical  ? ? ? ? ?8.5–8.7
Paliperidone palmitate Invega Sustenna Atypical Water a39–819 mg/4–12 weeks13–33 days25–139 days ?8.1–10.1
Perphenazine decanoate Trilafon Dekanoat Typical Sesame oil 50–200 mg/2–4 weeks ? ?27 days8.9
Perphenazine enanthate Trilafon Enanthate Typical Sesame oil 25–200 mg/2 weeks2–3 days ?4–7 days6.4–7.2 [26]
Pipotiazine palmitate Piportil Longum Typical Viscoleo b25–400 mg/4 weeks9–10 days ?14–21 days8.5–11.6 [19]
Pipotiazine undecylenate Piportil Medium Typical Sesame oil 100–200 mg/2 weeks ? ? ?8.4
Risperidone Risperdal Consta Atypical Microspheres 12.5–75 mg/2 weeks21 days ?3–6 days–
Zuclopentixol acetateClopixol Acuphase Typical Viscoleo b50–200 mg/1–3 days1–2 days1–2 days4.7–4.9
Zuclopentixol decanoateClopixol Depot Typical Viscoleo b50–800 mg/2–4 weeks4–9 days ?11–21 days7.5–9.0
Note: All by intramuscular injection. Footnotes:a = Microcrystalline or nanocrystalline aqueous suspension. b = Low-viscosity vegetable oil (specifically fractionated coconut oil with medium-chain triglycerides). c = Predicted, from PubChem and DrugBank. Sources:Main: See template.

History

Zuclopenthixol was introduced by Lundbeck in 1978. [27]

Related Research Articles

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References

  1. ↑ "Clopixol (Zuclopenthixol Hydrochloride) Film-coated tablets". Australian Product Information. Australia: The Therapeutics Goods Administration. Archived from the original on 2018-06-15. Retrieved 2013-08-08.
  2. ↑ Anvisa (2023-03-31). "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 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  3. ↑ Sneader, Walter (2005). Drug discovery: a history. New York: Wiley. p. 410. ISBN   0-471-89980-1. Archived from the original on 2023-04-29. Retrieved 2020-10-07.
  4. ↑ Christensen AV, Arnt J, Hyttel J, Larsen JJ, Svendsen O (April 1984). "Pharmacological effects of a specific dopamine D-1 antagonist SCH 23390 in comparison with neuroleptics". Life Sciences. 34 (16): 1529–1540. doi:10.1016/0024-3205(84)90607-6. PMID   6144029.
  5. ↑ Green AI, Noordsy DL, Brunette MF, O'Keefe C (January 2008). "Substance abuse and schizophrenia: pharmacotherapeutic intervention". Journal of Substance Abuse Treatment. 34 (1): 61–71. doi:10.1016/j.jsat.2007.01.008. PMC   2930488 . PMID   17574793.
  6. ↑ Sweetman, Sean C., ed. (2009). "Anxiolytic Sedatives Hypnotics and Antipsychotics". Martindale: The complete drug reference (36th ed.). London: Pharmaceutical Press. pp. 1040–1. ISBN   978-0-85369-840-1.
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  8. ↑ Haessler F, Glaser T, Beneke M, Pap AF, Bodenschatz R, Reis O (2007). "Zuclopenthixol in adults with intellectual disabilities and aggressive behaviours". British Journal of Psychiatry . 190 (5): 447–448. doi: 10.1192/bjp.bp.105.016535 . PMID   17470962.
  9. ↑ Lundbeck P/L (1991). "Clopixol Acuphase 50 mg/mL Injection Clopixol Acuphase 100 mg / 2 mL Injection". Lundbeck P/L. Archived from the original on 2007-06-09. Retrieved 2007-06-12.
  10. 1 2 Bryan EJ, Purcell MA, Kumar A (November 2017). "Zuclopenthixol dihydrochloride for schizophrenia". The Cochrane Database of Systematic Reviews. 2017 (11): CD005474. doi:10.1002/14651858.CD005474.pub2. PMC   6486001 . PMID   29144549.
  11. ↑ "Clopixol 2 mg film-coated tablets - Summary of Product Characteristics (SmPC) - (emc)". www.medicines.org.uk. Archived from the original on 2023-03-28. Retrieved 2023-03-28.
  12. ↑ "Clopixol 2 mg film-coated tablets - Summary of Product Characteristics (SmPC) - (emc)". www.medicines.org.uk.
  13. ↑ "UpToDate". www.uptodate.com.
  14. ↑ "Summary of Product Characteristics" (PDF). Archived (PDF) from the original on 2017-03-28. Retrieved 2017-03-28.
  15. 1 2 3 4 5 "TGA eBS - Product and Consumer Medicine Information Licence". Archived from the original on 2018-06-15. Retrieved 2013-08-08.
  16. ↑ Davies SJ, Westin AA, Castberg I, Lewis G, Lennard MS, Taylor S, Spigset O (2010). "Characterisation of zuclopenthixol metabolism by in vitro and therapeutic drug monitoring studies". Acta Psychiatrica Scandinavica . 122 (6): 445–453. doi:10.1111/j.1600-0447.2010.01619.x. PMID   20946203. S2CID   41869401.
  17. ↑ Parent M, Toussaint C, Gilson H (1983). "Long-term treatment of chronic psychotics with bromperidol decanoate: clinical and pharmacokinetic evaluation". Current Therapeutic Research. 34 (1): 1–6.
  18. 1 2 Jørgensen A, Overø KF (1980). "Clopenthixol and flupenthixol depot preparations in outpatient schizophrenics. III. Serum levels". Acta Psychiatrica Scandinavica. Supplementum. 279: 41–54. doi:10.1111/j.1600-0447.1980.tb07082.x. PMID   6931472.
  19. 1 2 Reynolds JE (1993). "Anxiolytic sedatives, hypnotics and neuroleptics.". Martindale: The Extra Pharmacopoeia (30th ed.). London: Pharmaceutical Press. pp. 364–623.
  20. ↑ Ereshefsky L, Saklad SR, Jann MW, Davis CM, Richards A, Seidel DR (May 1984). "Future of depot neuroleptic therapy: pharmacokinetic and pharmacodynamic approaches". The Journal of Clinical Psychiatry. 45 (5 Pt 2): 50–9. PMID   6143748.
  21. 1 2 Curry SH, Whelpton R, de Schepper PJ, Vranckx S, Schiff AA (April 1979). "Kinetics of fluphenazine after fluphenazine dihydrochloride, enanthate and decanoate administration to man". British Journal of Clinical Pharmacology. 7 (4): 325–31. doi:10.1111/j.1365-2125.1979.tb00941.x. PMC   1429660 . PMID   444352.
  22. ↑ Young D, Ereshefsky L, Saklad SR, Jann MW, Garcia N (1984). Explaining the pharmacokinetics of fluphenazine through computer simulations. (Abstract.). 19th Annual Midyear Clinical Meeting of the American Society of Hospital Pharmacists. Dallas, Texas.
  23. ↑ Janssen PA, Niemegeers CJ, Schellekens KH, Lenaerts FM, Verbruggen FJ, van Nueten JM, Marsboom RH, Hérin VV, Schaper WK (November 1970). "The pharmacology of fluspirilene (R 6218), a potent, long-acting and injectable neuroleptic drug". Arzneimittel-Forschung. 20 (11): 1689–98. PMID   4992598.
  24. ↑ Beresford R, Ward A (January 1987). "Haloperidol decanoate. A preliminary review of its pharmacodynamic and pharmacokinetic properties and therapeutic use in psychosis". Drugs. 33 (1): 31–49. doi:10.2165/00003495-198733010-00002. PMID   3545764.
  25. ↑ Reyntigens AJ, Heykants JJ, Woestenborghs RJ, Gelders YG, Aerts TJ (1982). "Pharmacokinetics of haloperidol decanoate. A 2-year follow-up". International Pharmacopsychiatry. 17 (4): 238–46. doi:10.1159/000468580. PMID   7185768.
  26. ↑ Larsson M, Axelsson R, Forsman A (1984). "On the pharmacokinetics of perphenazine: a clinical study of perphenazine enanthate and decanoate". Current Therapeutic Research. 36 (6): 1071–88.
  27. ↑ William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia. Elsevier. pp. 1102–. ISBN   978-0-8155-1856-3. Archived from the original on 14 January 2023. Retrieved 27 September 2017.
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