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Oxyprothepin decanoate

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(Redirected from Oxyprothepin) Antipsychotic medication Pharmaceutical compound
Oxyprothepin decanoate
Clinical data
Trade namesMeclopin
Routes of
administration		Intramuscular injection
Drug classTypical antipsychotic
ATC code
  • none
Pharmacokinetic data
Duration of action2–3 weeks
Identifiers
IUPAC name
  • 3-benzothiepin-5-yl)piperazin-1-yl]propyl decanoate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.050.520 Edit this at Wikidata
Chemical and physical data
FormulaC32H46N2O2S2
Molar mass554.85 g·mol
3D model (JSmol)
SMILES
  • CCCCCCCCCC(=O)OCCCN1CCN(CC1)C2CC3=CC=CC=C3SC4=C2C=C(C=C4)SC
InChI
  • InChI=1S/C32H46N2O2S2/c1-3-4-5-6-7-8-9-15-32(35)36-23-12-18-33-19-21-34(22-20-33)29-24-26-13-10-11-14-30(26)38-31-17-16-27(37-2)25-28(29)31/h10-11,13-14,16-17,25,29H,3-9,12,15,18-24H2,1-2H3
  • Key:SUVSVBSQNAUQJU-UHFFFAOYSA-N

Oxyprothepin decanoate, sold under the brand name Meclopin, is a typical antipsychotic which was used in the treatment of schizophrenia in the Czech Republic but is no longer marketed. It is administered by depot injection into muscle. The medication has an approximate duration of 2 to 3 weeks. The history of oxyprothepin decanoate has been reviewed.

Pharmacokinetics of long-acting injectable antipsychotics
Medication Brand name Class Vehicle Dosage Tmax t1/2 single t1/2 multiple logP Ref
Aripiprazole lauroxil Aristada Atypical Water 441–1064 mg/4–8 weeks 24–35 days ? 54–57 days 7.9–10.0
Aripiprazole monohydrate Abilify Maintena Atypical Water 300–400 mg/4 weeks 7 days ? 30–47 days 4.9–5.2
Bromperidol decanoate Impromen Decanoas Typical Sesame oil 40–300 mg/4 weeks 3–9 days ? 21–25 days 7.9
Clopentixol decanoate Sordinol Depot Typical Viscoleo 50–600 mg/1–4 weeks 4–7 days ? 19 days 9.0
Flupentixol decanoate Depixol Typical Viscoleo 10–200 mg/2–4 weeks 4–10 days 8 days 17 days 7.2–9.2
Fluphenazine decanoate Prolixin Decanoate Typical Sesame oil 12.5–100 mg/2–5 weeks 1–2 days 1–10 days 14–100 days 7.2–9.0
Fluphenazine enanthate Prolixin Enanthate Typical Sesame oil 12.5–100 mg/1–4 weeks 2–3 days 4 days ? 6.4–7.4
Fluspirilene Imap, Redeptin Typical Water 2–12 mg/1 week 1–8 days 7 days ? 5.2–5.8
Haloperidol decanoate Haldol Decanoate Typical Sesame oil 20–400 mg/2–4 weeks 3–9 days 18–21 days 7.2–7.9
Olanzapine pamoate Zyprexa Relprevv Atypical Water 150–405 mg/2–4 weeks 7 days ? 30 days –
Oxyprothepin decanoate Meclopin Typical ? ? ? ? ? 8.5–8.7
Paliperidone palmitate Invega Sustenna Atypical Water 39–819 mg/4–12 weeks 13–33 days 25–139 days ? 8.1–10.1
Perphenazine decanoate Trilafon Dekanoat Typical Sesame oil 50–200 mg/2–4 weeks ? ? 27 days 8.9
Perphenazine enanthate Trilafon Enanthate Typical Sesame oil 25–200 mg/2 weeks 2–3 days ? 4–7 days 6.4–7.2
Pipotiazine palmitate Piportil Longum Typical Viscoleo 25–400 mg/4 weeks 9–10 days ? 14–21 days 8.5–11.6
Pipotiazine undecylenate Piportil Medium Typical Sesame oil 100–200 mg/2 weeks ? ? ? 8.4
Risperidone Risperdal Consta Atypical Microspheres 12.5–75 mg/2 weeks 21 days ? 3–6 days –
Zuclopentixol acetate Clopixol Acuphase Typical Viscoleo 50–200 mg/1–3 days 1–2 days 1–2 days 4.7–4.9
Zuclopentixol decanoate Clopixol Depot Typical Viscoleo 50–800 mg/2–4 weeks 4–9 days ? 11–21 days 7.5–9.0
Note: All by intramuscular injection. Footnotes: = Microcrystalline or nanocrystalline aqueous suspension. = Low-viscosity vegetable oil (specifically fractionated coconut oil with medium-chain triglycerides). = Predicted, from PubChem and DrugBank. Sources: Main: See template.

References

  1. ^ Ross J. Baldessarini (1985). Chemotherapy in Psychiatry: Principles and Practice. Harvard University Press. pp. 36–. ISBN 978-0-674-11383-1.
  2. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 781–. ISBN 978-3-88763-075-1.
  3. De Risio A, Lang AP (February 2014). "History and therapeutic rationale of long acting antipsychotics". Curr Clin Pharmacol. 9 (1): 39–52. doi:10.2174/15748847113089990057. PMID 23343446.
  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. ^ 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. ^ 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. ^ 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.


Antipsychotics (N05A)
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