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Fluspirilene

February 24, 2023

Fluspirilene (Redeptin, Imap, R6218) is a diphenylbutylpiperidine typical antipsychotic drug, used for the treatment of schizophrenia.[1] It is administered intramuscularly.[2] It was discovered at Janssen Pharmaceutica in 1963.[3] A 2007 systematic review investigated the efficacy of fluspirilene decanoate for people with schizophrenia:

Fluspirilene
Clinical data
Trade namesImap
AHFS/Drugs.comInternational Drug Names
Routes of
administration		IM
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • 8-[4,4-Bis(4-fluorophenyl)butyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one
CAS Number
  • 1841-19-6 Y
PubChem CID
  • 3396
IUPHAR/BPS
  • 85
DrugBank
  • DB04842 Y
ChemSpider
  • 3279 Y
UNII
  • C5QA4GLR9M
KEGG
  • D02629 Y
ChEMBL
  • ChEMBL46516 Y
CompTox Dashboard (EPA)
  • DTXSID7045152
ECHA InfoCard100.015.835
Chemical and physical data
FormulaC29H31F2N3O
Molar mass475.584 g·mol−1
3D model (JSmol)
  • Interactive image
  • Fc1ccc(cc1)C(c2ccc(F)cc2)CCCN5CCC4(C(=O)NCN4c3ccccc3)CC5
  • InChI=1S/C29H31F2N3O/c30-24-12-8-22(9-13-24)27(23-10-14-25(31)15-11-23)7-4-18-33-19-16-29(17-20-33)28(35)32-21-34(29)26-5-2-1-3-6-26/h1-3,5-6,8-15,27H,4,7,16-21H2,(H,32,35) Y
  • Key:QOYHHIBFXOOADH-UHFFFAOYSA-N Y
  (verify)
Fluspirilene decanoate compared to oral antipsychotics[4]
Summary
Participant numbers in each comparison were small so power to identify clear difference is limited. Randomized controlled trial data identified no clear differences between the long-acting injection of fluspirilene and oral medication for outcomes that include adverse effects.[4]
Pharmacokinetics of long-acting injectable antipsychotics
Medication Brand name Class Vehicle Dosage Tmax t1/2 single t1/2 multiple logPc Ref
Aripiprazole lauroxil Aristada Atypical Watera 441–1064 mg/4–8 weeks 24–35 days ? 54–57 days 7.9–10.0
Aripiprazole monohydrate Abilify Maintena Atypical Watera 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 Viscoleob 50–600 mg/1–4 weeks 4–7 days ? 19 days 9.0 [6]
Flupentixol decanoate Depixol Typical Viscoleob 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 Watera 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 Watera 150–405 mg/2–4 weeks 7 days ? 30 days –
Oxyprothepin decanoate Meclopin Typical ? ? ? ? ? 8.5–8.7
Paliperidone palmitate Invega Sustenna Atypical Watera 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 Viscoleob 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 Viscoleob 50–200 mg/1–3 days 1–2 days 1–2 days 4.7–4.9
Zuclopentixol decanoate Clopixol Depot Typical Viscoleob 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.

Synthesis

 
Synthesis:[15][16] Patents:[17][18]

1,1'-(4-Chlorobutylidene)bis(4-fluorobenzene) [3312-04-7] (1) & 1-Phenyl-1,3,8-Triazaspiro[4.5]Decan-4-One [1021-25-6] (2) give Fluspiriline (3).

See also

References

  1. ^ van Epen JH (1970). "Experience with fluspirilene (R 6218), a long-acting neuroleptic". Psychiatr Neurol Neurochir. 73 (4): 277–284. PMID 5478771.
  2. ^ Janssen PA, Niemegeers CJ, Schellekens KH, Lenaerts FM, Verbruggen FJ, van Nueten JM, Marsboom RH, Hérin VV, Schaper WK (1970). "The pharmacology of fluspirilene (R 6218), a potent, long-acting and injectable neuroleptic drug". Arzneimittelforschung. 20 (11): 1689–1698. PMID 4992598.
  3. ^ C. Janssen, NV Res. Lab., BE 633914  (1963)
  4. ^ a b Abhijnhan, A; Adams, C; David, A (2007). "Depot fluspirilene for schizophrenia". Cochrane Database of Systematic Reviews. 1 (1): CD001718.pub2. doi:10.1002/14651858.CD001718.pub2. PMC 7025783. PMID 17253464.
  5. ^ 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.
  6. ^ a b 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.
  7. ^ a b Reynolds JE (1993). "Anxiolytic sedatives, hypnotics and neuroleptics.". Martindale: The Extra Pharmacopoeia (30th ed.). London: Pharmaceutical Press. pp. 364–623.
  8. ^ 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.
  9. ^ a b 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.
  10. ^ 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.
  11. ^ Janssen PA, Niemegeers CJ, Schellekens KH, Lenaerts FM, Verbruggen FJ, van Nueten JM, et al. (November 1970). "The pharmacology of fluspirilene (R 6218), a potent, long-acting and injectable neuroleptic drug". Arzneimittel-Forschung. 20 (11): 1689–98. PMID 4992598.
  12. ^ 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.
  13. ^ 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.
  14. ^ 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.
  15. ^ Schmidt, Andreas; Marchetti, Mauro; Eilbracht, Peter (2004). "Regioselective hydroaminomethylation of 1,1-diaryl-allyl-alcohols: a new access to 4,4-diarylbutylamines". Tetrahedron. 60 (50): 11487–11492. doi:10.1016/j.tet.2004.09.058.
  16. ^ Botteghi, C., Marchetti, M., Paganelli, S., Persi-Paoli, F. (February 2001). "Rhodium catalyzed hydroformylation of 1,1-bis(p-fluorophenyl)allyl or propargyl alcohol: a key step in the synthesis of Fluspirilen and Penfluridol". Tetrahedron. 57 (8): 1631–1637. doi:10.1016/S0040-4020(00)01151-0. ISSN 0040-4020.
  17. ^ Janssen Paul Adriaan Jan, U.S. Patent 3,238,216 (1966 to Res Lab Dr C Janssen N V); CA, 65, 8924d
  18. ^ BE633914 idem Jan Janssen Paul Adrian, GB 1043141  (1966 to Janssen Pharmaceutica Nv).
 

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February 24, 2023
fluspirilene, redeptin, imap, r6218, diphenylbutylpiperidine, typical, antipsychotic, drug, used, treatment, schizophrenia, administered, intramuscularly, discovered, janssen, pharmaceutica, 1963, 2007, systematic, review, investigated, efficacy, fluspirilene,. Fluspirilene Redeptin Imap R6218 is a diphenylbutylpiperidine typical antipsychotic drug used for the treatment of schizophrenia 1 It is administered intramuscularly 2 It was discovered at Janssen Pharmaceutica in 1963 3 A 2007 systematic review investigated the efficacy of fluspirilene decanoate for people with schizophrenia FluspirileneClinical dataTrade namesImapAHFS Drugs comInternational Drug NamesRoutes ofadministrationIMATC codeN05AG01 WHO Legal statusLegal statusIn general Prescription only IdentifiersIUPAC name 8 4 4 Bis 4 fluorophenyl butyl 1 phenyl 1 3 8 triazaspiro 4 5 decan 4 oneCAS Number1841 19 6 YPubChem CID3396IUPHAR BPS85DrugBankDB04842 YChemSpider3279 YUNIIC5QA4GLR9MKEGGD02629 YChEMBLChEMBL46516 YCompTox Dashboard EPA DTXSID7045152ECHA InfoCard100 015 835Chemical and physical dataFormulaC 29H 31F 2N 3OMolar mass475 584 g mol 13D model JSmol Interactive imageSMILES Fc1ccc cc1 C c2ccc F cc2 CCCN5CCC4 C O NCN4c3ccccc3 CC5InChI InChI 1S C29H31F2N3O c30 24 12 8 22 9 13 24 27 23 10 14 25 31 15 11 23 7 4 18 33 19 16 29 17 20 33 28 35 32 21 34 29 26 5 2 1 3 6 26 h1 3 5 6 8 15 27H 4 7 16 21H2 H 32 35 YKey QOYHHIBFXOOADH UHFFFAOYSA N Y verify Fluspirilene decanoate compared to oral antipsychotics 4 SummaryParticipant numbers in each comparison were small so power to identify clear difference is limited Randomized controlled trial data identified no clear differences between the long acting injection of fluspirilene and oral medication for outcomes that include adverse effects 4 Outcome Findings in words Findings in numbers Quality of evidenceGlobal outcomeLeaving the study earlyFollow up 6 weeks to 5 months Fluspirilene decanoate may increase the risk of leaving the study reasons not specified but the difference is not clear between people given fluspirilene decanoate and those receiving oral antipsychotics These findings are based on data of low quality RR 1 18 0 08 to 16 78 LowMental stateRelapseFollow up 6 weeks to 5 months Using the depot long acting fluspirilene decanoate makes little difference for the outcome of relapse compared with those receiving oral antipsychotics at least for those willing to be engaged with trials These findings are based on data of low quality RR 1 18 0 08 to 16 78 LowAdverse effectsNeeding anticholinergic drugsFollow up 6 weeks to 5 months The depot fluspirilene decanoate does not seem to cause any more movement disorders for which anticholinergic drugs are used compared with oral antipsychotics These findings are based on data of low quality RR 0 07 0 00 to 1 07 LowDizziness Fluspirilene decanoate may reduce the chance of experiencing dizziness compared with the oral antipsycotics Data are based on low quality evidence RR 0 59 0 37 to 0 95 LowMissing outcomesData on quality of life and service use e g hospitalization were not reported in trials vte Pharmacokinetics of long acting injectable antipsychotics Medication Brand name Class Vehicle Dosage Tmax t1 2 single t1 2 multiple logPc RefAripiprazole lauroxil Aristada Atypical Watera 441 1064 mg 4 8 weeks 24 35 days 54 57 days 7 9 10 0Aripiprazole monohydrate Abilify Maintena Atypical Watera 300 400 mg 4 weeks 7 days 30 47 days 4 9 5 2Bromperidol 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 Viscoleob 50 600 mg 1 4 weeks 4 7 days 19 days 9 0 6 Flupentixol decanoate Depixol Typical Viscoleob 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 Watera 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 Watera 150 405 mg 2 4 weeks 7 days 30 days Oxyprothepin decanoate Meclopin Typical 8 5 8 7Paliperidone palmitate Invega Sustenna Atypical Watera 39 819 mg 4 12 weeks 13 33 days 25 139 days 8 1 10 1Perphenazine decanoate Trilafon Dekanoat Typical Sesame oil 50 200 mg 2 4 weeks 27 days 8 9Perphenazine 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 Viscoleob 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 4Risperidone Risperdal Consta Atypical Microspheres 12 5 75 mg 2 weeks 21 days 3 6 days Zuclopentixol acetate Clopixol Acuphase Typical Viscoleob 50 200 mg 1 3 days 1 2 days 1 2 days 4 7 4 9Zuclopentixol decanoate Clopixol Depot Typical Viscoleob 50 800 mg 2 4 weeks 4 9 days 11 21 days 7 5 9 0Note 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 Synthesis EditSidechain precursor 3312 04 7 1 also used for penfluridol clopimozide amperozide pimozide lidoflazine Piperidine 1021 25 6 also used for Spiroxantrine Spiperone Ro65 6570 RP 23618 Spirilene Spiramide R 5260 1109 69 9 etc Synthesis 15 16 Patents 17 18 1 1 4 Chlorobutylidene bis 4 fluorobenzene 3312 04 7 1 amp 1 Phenyl 1 3 8 Triazaspiro 4 5 Decan 4 One 1021 25 6 2 give Fluspiriline 3 See also EditPimozide Penfluridol Spiperone Mosapramine atypical antipsychotic References Edit van Epen JH 1970 Experience with fluspirilene R 6218 a long acting neuroleptic Psychiatr Neurol Neurochir 73 4 277 284 PMID 5478771 Janssen PA Niemegeers CJ Schellekens KH Lenaerts FM Verbruggen FJ van Nueten JM Marsboom RH Herin VV Schaper WK 1970 The pharmacology of fluspirilene R 6218 a potent long acting and injectable neuroleptic drug Arzneimittelforschung 20 11 1689 1698 PMID 4992598 C Janssen NV Res Lab BE 633914 1963 a b Abhijnhan A Adams C David A 2007 Depot fluspirilene for schizophrenia Cochrane Database of Systematic Reviews 1 1 CD001718 pub2 doi 10 1002 14651858 CD001718 pub2 PMC 7025783 PMID 17253464 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 b Jorgensen A Overo 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 b Reynolds 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 b 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 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 et al 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 Schmidt Andreas Marchetti Mauro Eilbracht Peter 2004 Regioselective hydroaminomethylation of 1 1 diaryl allyl alcohols a new access to 4 4 diarylbutylamines Tetrahedron 60 50 11487 11492 doi 10 1016 j tet 2004 09 058 Botteghi C Marchetti M Paganelli S Persi Paoli F February 2001 Rhodium catalyzed hydroformylation of 1 1 bis p fluorophenyl allyl or propargyl alcohol a key step in the synthesis of Fluspirilen and Penfluridol Tetrahedron 57 8 1631 1637 doi 10 1016 S0040 4020 00 01151 0 ISSN 0040 4020 Janssen Paul Adriaan Jan U S Patent 3 238 216 1966 to Res Lab Dr C Janssen N V CA 65 8924d BE633914 idem Jan Janssen Paul Adrian GB 1043141 1966 to Janssen Pharmaceutica Nv This drug article relating to the nervous system is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Fluspirilene amp oldid 1123923086, wikipedia, wiki, book, books, library,

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