Oxyprothepin decanoate

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.[2] It is administered by depot injection into muscle.[2] The medication has an approximate duration of 2 to 3 weeks.[1] The history of oxyprothepin decanoate has been reviewed.[3]

Pharmacokinetics of long-acting injectable antipsychotics

Medication	Brand name	Class	Vehicle	Dosage	Tmax	t1/2 single	t1/2 multiple	logP^c	Ref
Aripiprazole lauroxil	Aristada	Atypical	Water^a	441–1064 mg/4–8 weeks	24–35 days	?	54–57 days	7.9–10.0
Aripiprazole monohydrate	Abilify Maintena	Atypical	Water^a	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	[4]
Clopentixol decanoate	Sordinol Depot	Typical	Viscoleo^b	50–600 mg/1–4 weeks	4–7 days	?	19 days	9.0	[5]
Flupentixol decanoate	Depixol	Typical	Viscoleo^b	10–200 mg/2–4 weeks	4–10 days	8 days	17 days	7.2–9.2	[5][6]
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	[7][8][9]
Fluphenazine enanthate	Prolixin Enanthate	Typical	Sesame oil	12.5–100 mg/1–4 weeks	2–3 days	4 days	?	6.4–7.4	[8]
Fluspirilene	Imap, Redeptin	Typical	Water^a	2–12 mg/1 week	1–8 days	7 days	?	5.2–5.8	[10]
Haloperidol decanoate	Haldol Decanoate	Typical	Sesame oil	20–400 mg/2–4 weeks	3–9 days	18–21 days		7.2–7.9	[11][12]
Olanzapine pamoate	Zyprexa Relprevv	Atypical	Water^a	150–405 mg/2–4 weeks	7 days	?	30 days	–
Oxyprothepin decanoate	Meclopin	Typical	?	?	?	?	?	8.5–8.7
Paliperidone palmitate	Invega Sustenna	Atypical	Water^a	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	[13]
Pipotiazine palmitate	Piportil Longum	Typical	Viscoleo^b	25–400 mg/4 weeks	9–10 days	?	14–21 days	8.5–11.6	[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 weeks	21 days	?	3–6 days	–
Zuclopentixol acetate	Clopixol Acuphase	Typical	Viscoleo^b	50–200 mg/1–3 days	1–2 days	1–2 days		4.7–4.9
Zuclopentixol decanoate	Clopixol Depot	Typical	Viscoleo^b	50–800 mg/2–4 weeks	4–9 days	?	11–21 days	7.5–9.0
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.

Oxyprothepin decanoate

Clinical data
Trade names	Meclopin
Routes of administration	Intramuscular injection
Drug class	Typical antipsychotic
ATC code	none
Pharmacokinetic data
Duration of action	2–3 weeks[1]
Identifiers
IUPAC name 3-[4-(3-methylsulfanyl-5,6-dihydrobenzo[b][1]benzothiepin-5-yl)piperazin-1-yl]propyl decanoate
CAS Number	41931-86-6
PubChem CID	93233
ChemSpider	84173
UNII	KFH034QDI8
Chemical and physical data
Formula	C32H46N2O2S2
Molar mass	554.85 g·mol^−1
3D model (JSmol)	Interactive image
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

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. https://scholar.google.com/scholar?cites=10379409109713994773
5. Jørgensen A, Overø KF (1980). "Clopenthixol and flupenthixol depot preparations in outpatient schizophrenics. III. Serum levels". Acta Psychiatr Scand Suppl. 279: 41–54. doi:10.1111/j.1600-0447.1980.tb07082.x. PMID 6931472.
6. Reynolds, J. E. F. (1993). Anxiolytic sedatives, hypnotics and neuroleptics. Martindale: The Extra Pharmacopoeia, 30th Edition (pp. 364–623). Pharmaceutical Press, London. https://scholar.google.com/scholar?cluster=8335042449033257176
7. Ereshefsky L, Saklad SR, Jann MW, Davis CM, Richards A, Seidel DR (May 1984). "Future of depot neuroleptic therapy: pharmacokinetic and pharmacodynamic approaches". J Clin 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". Br J Clin Pharmacol. 7 (4): 325–31. doi:10.1111/j.1365-2125.1979.tb00941.x. PMC 1429660. PMID 444352.
9. Young. D.: Ereshefsky. L.: Saklad. S.R.; Jann. M.W. and Garcia. N.: Explaining the pharmacokinetics of fluphenazine through computer simulations. (Abstract.) Presented at the 19th Annual Midyear Clinical Meeting of the American Society of Hospital Pharmacists. Dallas. Texas (1984).
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". Arzneimittelforschung. 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". Int 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), 1071–1088. https://scholar.google.com/scholar?cluster=12503004172250709786