Clopenthixol

Last updated
Clopenthixol
Clopenthixol structure.svg
Clinical data
Routes of
administration 		Oral
ATC code
Identifiers
  • (E,Z)-2-[4-[3-(2-chlorothioxanthen-9-ylidene) propyl]piperazin-1-yl]ethanol
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.012.333 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)=CCCN4CCN(CCO)CC4
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Clopenthixol (Sordinol), also known as clopentixol, is a typical antipsychotic drug of the thioxanthene class. It was introduced by Lundbeck in 1961. [1]

Clopenthixol is a mixture of cis and trans isomers. Zuclopenthixol, the pure cis isomer, was later introduced by Lundbeck in 1962, [2] and has been much more widely used. Both drugs are equally effective as antipsychotics and have similar adverse effect profiles, but clopenthixol is half as active on a milligram-to-milligram basis and appears to produce more sedation in comparison. [3]

Clopenthixol is not approved for use in the United States.

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 [4]
Clopentixol decanoateSordinol Depot Typical Viscoleo b50–600 mg/1–4 weeks4–7 days ?19 days9.0 [5]
Flupentixol decanoate Depixol Typical Viscoleo b10–200 mg/2–4 weeks4–10 days8 days17 days7.2–9.2 [5] [6]
Fluphenazine decanoate Prolixin Decanoate Typical Sesame oil 12.5–100 mg/2–5 weeks1–2 days1–10 days14–100 days7.2–9.0 [7] [8] [9]
Fluphenazine enanthate Prolixin Enanthate Typical Sesame oil 12.5–100 mg/1–4 weeks2–3 days4 days ?6.4–7.4 [8]
Fluspirilene Imap, Redeptin Typical Water a2–12 mg/1 week1–8 days7 days ?5.2–5.8 [10]
Haloperidol decanoate Haldol Decanoate Typical Sesame oil 20–400 mg/2–4 weeks3–9 days18–21 days7.2–7.9 [11] [12]
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 [13]
Pipotiazine palmitate Piportil Longum Typical Viscoleo b25–400 mg/4 weeks9–10 days ?14–21 days8.5–11.6 [6]
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 acetate Clopixol Acuphase Typical Viscoleo b50–200 mg/1–3 days1–2 days1–2 days4.7–4.9
Zuclopentixol decanoate Clopixol 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.

References

  1. ↑ Sneader W (2005). Drug discovery: a history. New York: Wiley. p. 410. ISBN   0-471-89980-1.
  2. ↑ Vela JM, Buschmann H, Holenz J, Párraga A, Torrens A (2007). Antidepressants, Antipsychotics, Anxiolytics: From Chemistry and Pharmacology to Clinical Application. Weinheim: Wiley-VCH. p. 516. ISBN   978-3-527-31058-6.[ permanent dead link ]
  3. ↑ Gravem A, Engstrand E, Guleng RJ (November 1978). "Cis(Z)-clopenthixol and clopenthixol (Sordinol) in chronic psychotic patients. A double-blind clinical investigation". Acta Psychiatrica Scandinavica. 58 (5): 384–388. doi:10.1111/j.1600-0447.1978.tb03570.x. PMID   362830. S2CID   44833311.
  4. ↑ 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.
  5. 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.
  6. 1 2 Reynolds JE (1993). "Anxiolytic sedatives, hypnotics and neuroleptics.". Martindale: The Extra Pharmacopoeia (30th ed.). London: Pharmaceutical Press. pp. 364–623.
  7. ↑ 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.
  8. 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.
  9. ↑ 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.
  10. ↑ 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.
  11. ↑ 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.
  12. ↑ 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.
  13. ↑ 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.
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