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Bromperidol decanoate

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Chemical compound

Pharmaceutical compound

Bromperidol decanoate
Clinical data

Trade names	Bromidol Depot, Bromodol Decanoato, Impromen Decanoas
Other names	R-46541; R-46,541
Routes of administration	Intramuscular injection
Drug class	Typical antipsychotic
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name [4-(4-bromophenyl)-1-[4-(4-fluorophenyl)-4-oxobutyl]piperidin-4-yl] decanoate
CAS Number	75067-66-2
PubChemCID	156321
ChemSpider	137658
UNII	73LG72M4LV
KEGG	D02626
ChEMBL	ChEMBL2106135
CompTox Dashboard(EPA)	DTXSID30226039
ECHA InfoCard	100.070.947
Chemical and physical data
Formula	C₃₁H₄₁BrFNO₃
Molar mass	574.575 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCCCCCCC(=O)OC1(CCN(CC1)CCCC(=O)C2=CC=C(C=C2)F)C3=CC=C(C=C3)Br
InChI InChI=1S/C31H41BrFNO3/c1-2-3-4-5-6-7-8-11-30(36)37-31(26-14-16-27(32)17-15-26)20-23-34(24-21-31)22-9-10-29(35)25-12-18-28(33)19-13-25/h12-19H,2-11,20-24H2,1H3 Key:ZINCPWWBSRSXBH-UHFFFAOYSA-N

Bromperidol decanoate, sold under the brand namesBromidol Depot,Bromodol Decanoato, andImpromen Decanoas, is anantipsychotic which has been marketed inEurope andLatin America.^[1]^[2] It is anantipsychotic ester and long-actingprodrug ofbromperidol which is administered bydepot intramuscular injection once every 4 weeks.^[3]^[4]

v
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Pharmacokinetics of long-acting injectable antipsychotics
Medication	Brand name	Class	Vehicle	Dosage	T_max	t_1/2 single	t_1/2 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	^[5]
Clopentixol decanoate	Sordinol Depot	Typical	Viscoleo^b	50–600 mg/1–4 weeks	4–7 days	?	19 days	9.0	^[6]
Flupentixol decanoate	Depixol	Typical	Viscoleo^b	10–200 mg/2–4 weeks	4–10 days	8 days	17 days	7.2–9.2	^[6]^[7]
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	^[8]^[9]^[10]
Fluphenazine enanthate	Prolixin Enanthate	Typical	Sesame oil	12.5–100 mg/1–4 weeks	2–3 days	4 days	?	6.4–7.4	^[9]
Fluspirilene	Imap, Redeptin	Typical	Water^a	2–12 mg/1 week	1–8 days	7 days	?	5.2–5.8	^[11]
Haloperidol decanoate	Haldol Decanoate	Typical	Sesame oil	20–400 mg/2–4 weeks	3–9 days	18–21 days		7.2–7.9	^[12]^[13]
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	^[14]
Pipotiazine palmitate	Piportil Longum	Typical	Viscoleo^b	25–400 mg/4 weeks	9–10 days	?	14–21 days	8.5–11.6	^[7]
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 byintramuscular injection.Footnotes:^a =Microcrystalline ornanocrystalline aqueous suspension.^b = Low-viscosity vegetable oil (specificallyfractionated coconut oil withmedium-chain triglycerides).^c = Predicted, fromPubChem andDrugBank.Sources:Main: See template.

References

[edit]

^J. Elks, ed. (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 182–.ISBN 978-1-4757-2085-3.OCLC 1058412474.
^Swiss Pharmaceutical Society (2000). Swiss Pharmaceutical Society (ed.).Index Nominum 2000: International Drug Directory. Taylor & Francis. pp. 138–.ISBN 978-3-88763-075-1.
^Spanarello S, La Ferla T (2014). "The pharmacokinetics of long-acting antipsychotic medications".Curr Clin Pharmacol.9 (3):310–7.doi:10.2174/15748847113089990051.PMID 23343447.
^Davis JM, Matalon L, Watanabe MD, Blake L, Metalon L (May 1994). "Depot antipsychotic drugs. Place in therapy".Drugs.47 (5):741–73.doi:10.2165/00003495-199447050-00004.PMID 7520856.S2CID 46962898.
^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.
^^a ^bJørgensen 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.
^^a ^bReynolds JE (1993). "Anxiolytic sedatives, hypnotics and neuroleptics.".Martindale: The Extra Pharmacopoeia (30th ed.). London: Pharmaceutical Press. pp. 364–623.
^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.
^^a ^bCurry 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.
^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.
^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.
^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.
^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.
^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.INIST 8951670.

v t e Antipsychotics (N05A)
Typical	Butyrophenones:Benperidol Bromperidol Bromperidol decanoate Droperidol Haloperidol^# Haloperidol decanoate Moperone Pipamperone Spiperone Timiperone Trifluperidol Diphenylbutylpiperidines:Fluspirilene Penfluridol Pimozide Phenothiazines:Acepromazine Acetophenazine Butaperazine Carphenazine (carfenazine)^‡ Chlorpromazine Cyamemazine Dixyrazine Fluphenazine Fluphenazine decanoate Fluphenazine enanthate Levomepromazine (methotrimeprazine) Mesoridazine Perazine Periciazine Perphenazine BL-1020 Perphenazine decanoate Perphenazine enanthate Piperacetazine Pipotiazine Pipotiazine palmitate Pipotiazine undecylenate Prochlorperazine Promazine Sulforidazine Thiopropazate Thioproperazine Thioridazine Trifluoperazine Triflupromazine Thioxanthenes:Chlorprothixene Clopenthixol Clopenthixol decanoate Flupentixol Flupentixol decanoate Tiotixene (thiothixene) Zuclopenthixol Zuclopenthixol acetate Zuclopenthixol decanoate
Disputed	Benzamides:Amisulpride Levosulpiride Nemonapride Remoxipride^‡ Sulpiride Sultopride Tiapride Veralipride^‡ Butyrophenones:Melperone Tricyclics:Carpipramine Clocapramine Clorotepine Clotiapine Loxapine Mosapramine Oxyprothepin decanoate Others:Molindone
Atypical	Benzisoxazole/benzisothiazoles:Iloperidone Lurasidone Paliperidone Paliperidone palmitate Perospirone Risperidone^# Ziprasidone Butyrophenones:Lumateperone Phenylpiperazines/quinolinones:Aripiprazole Aripiprazole lauroxil Brilaroxazine^† Brexpiprazole Cariprazine Tricyclics:Asenapine Clozapine^# Olanzapine (+samidorphan) Quetiapine Zotepine Others:Blonanserin Pimavanserin Sertindole
Others	Monoamine-depleting agents:Oxypertine Reserpine Tetrabenazine Muscarinic agonists:Xanomeline/trospium chloride Others/unknown:Azacyclonol
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

Dopamine receptor modulators

D₁-like

Agonists	Benzazepines:6-Br-APB Fenoldopam SKF-38,393 SKF-77,434 SKF-81,297 SKF-82,958 SKF-83,959 Trepipam Zelandopam Ergolines:Cabergoline CY-208,243 Dihydroergocryptine LEK-8829 Lisuride Pergolide Terguride Dihydrexidine derivatives:A-77636 A-86929 Adrogolide (ABT-431, DAS-431) Dihydrexidine Dinapsoline Dinoxyline Doxanthrine Phenethylamines:BCO-001 Deoxyepinephrine (N-methyldopamine, epinine) Dopexamine Etilevodopa Ibopamine L-DOPA (levodopa) Melevodopa L-Phenylalanine L-Tyrosine XP21279 Others:A-68930 Apomorphine Isocorypalmine Nuciferine PF-6649751 PF 6669571 Propylnorapomorphine Rotigotine SKF-89,145 SKF-89,626 Stepholidine Tavapadon Tetrahydropalmatine
PAMs	Tetrahydroisoquinolines:DETQ DPTQ Mevidalen
Antagonists	Typical antipsychotics:Butaclamol Chlorpromazine Chlorprothixene Flupentixol (flupenthixol) (+melitracen) Fluphenazine Loxapine Perphenazine (+amitriptyline) Pifluthixol Thioridazine Thiothixene Trifluoperazine (+tranylcypromine) Zuclopenthixol Atypical antipsychotics:Asenapine Clorotepine Clotiapine Clozapine DHA-clozapine Fluperlapine Iloperidone Norclozapine Norquetiapine Olanzapine (+fluoxetine) Paliperidone Quetiapine Risperidone Tefludazine Zicronapine Ziprasidone Zotepine Others:Berupipam Ecopipam EEDQ Metitepine (methiothepin) Odapipam Perlapine SCH-23390