Pipotiazine

Pipotiazine
Clinical data
Trade names	Piportil
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral, IM
ATC code	N05AC04 (WHO) ;
Legal status
Legal status	BR: Class C1 (Other controlled substances); In general: ℞ (Prescription only);
Identifiers
	IUPAC name 10-[3-[4-(2-hydroxyethyl)-1-piperidyl]propyl]-N,N-dimethyl-phenothiazine-2-sulfonamide;
CAS Number	39860-99-6;
PubChem CID	62867;
IUPHAR/BPS	7557;
DrugBank	DB01621;
ChemSpider	56598;
UNII	L903J9JPYV;
KEGG	D08385;
ChEMBL	ChEMBL398880;
CompTox Dashboard (EPA)	DTXSID40192913 ;
ECHA InfoCard	100.049.672
Chemical and physical data
Formula	C24H33N3O3S2
Molar mass	475.67 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN(C)S(=O)(=O)C1=CC2=C(C=C1)SC3=CC=CC=C3N2CCCN4CCC(CC4)CCO;

Pipotiazine

Typical antipsychotic medication

Pipotiazine (Piportil), also known as pipothiazine, is a typical antipsychotic of the phenothiazine class^[2] used in the United Kingdom and other countries for the treatment of schizophrenia.^[3] Its properties are similar to those of chlorpromazine. A 2004 systematic review investigated its efficacy for people with schizophrenia:

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References

[1]
Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
[2]
Bechelli LP, Ruffino-Netto A, Hetem G (December 1983). "A double-blind controlled trial of pipotiazine, haloperidol and placebo in recently-hospitalized acute schizophrenic patients". Brazilian Journal of Medical and Biological Research. 16 (4): 305–11. PMID 6143579.
[3]
International Drug Names
[4]
Dinesh M, David A, Quraishi SN (October 2004). "Depot pipotiazine palmitate and undecylenate for schizophrenia". The Cochrane Database of Systematic Reviews. 3 (4): CD001720. doi:10.1002/14651858.CD001720.pub2. PMC 7025786. PMID 15495016.
[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]
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]
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]
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, 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.
[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]
"Piportil® L4 (pipotiazine palmitate)" (PDF). Archived from the original (PDF) on 2021-12-02. Retrieved 11 December 2023.
[16]
White J (July 2022). "Guidance on the Administration to Adults of Oil-based Depot and other Long-acting Intramuscular Antipsychotic Injections 7th Edition" (PDF). www.reach4resource.co.uk. Retrieved 11 December 2023.
[17]
, FR 7835M (1970).
[18]
ZA6801990 idem Jean-Claude Rene Georg Blondel, 2 More », U.S. patent 3,875,156 (1975 to Rhone Poulenc Sa).
[19]
Schussen, & Li Haixia, et al. CN 106568857 (2019 to YUEYANG XINHUADA PHARMACEUTICAL CO Ltd).
[20]
Haddad P, Taylor M, Patel MX, Taylor D (June 2015). "Guidance on switching away from Piportil Depot® (pipotiazine palmitate) injection". The British Journal of Psychiatry. 206 (6): 521. doi:10.1192/bjp.206.6.521. PMID 26034183.

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This article uses material from the Wikipedia article Pipotiazine, and is written by contributors. Text is available under a CC BY-SA 4.0 International License; additional terms may apply. Images, videos and audio are available under their respective licenses.

[1] [1]
Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[2] [2]
Bechelli LP, Ruffino-Netto A, Hetem G (December 1983). "A double-blind controlled trial of pipotiazine, haloperidol and placebo in recently-hospitalized acute schizophrenic patients". Brazilian Journal of Medical and Biological Research. 16 (4): 305–11. PMID 6143579.

[3] [3]
International Drug Names

[Din2004-4] [4]
Dinesh M, David A, Quraishi SN (October 2004). "Depot pipotiazine palmitate and undecylenate for schizophrenia". The Cochrane Database of Systematic Reviews. 3 (4): CD001720. doi:10.1002/14651858.CD001720.pub2. PMC 7025786. PMID 15495016.

[ParentToussaint1983-5] [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.

[pmid6931472-6] [6]
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.

[Reynolds1993-7] [7]
Reynolds JE (1993). "Anxiolytic sedatives, hypnotics and neuroleptics.". Martindale: The Extra Pharmacopoeia (30th ed.). London: Pharmaceutical Press. pp. 364–623.

[pmid6143748-8] [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.

[pmid444352-9] [9]
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.

[YoungEreshefsky1984-10] [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.

[pmid4992598-11] [11]
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.

[pmid3545764-12] [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.

[pmid7185768-13] [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.

[LarssonAxelsson1984-14] [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.

[Piportil_SmPC-15] [15]
"Piportil® L4 (pipotiazine palmitate)" (PDF). Archived from the original (PDF) on 2021-12-02. Retrieved 11 December 2023.

[16] [16]
White J (July 2022). "Guidance on the Administration to Adults of Oil-based Depot and other Long-acting Intramuscular Antipsychotic Injections 7th Edition" (PDF). www.reach4resource.co.uk. Retrieved 11 December 2023.

[17] [17]
, FR 7835M (1970).

[18] [18]
ZA6801990 idem Jean-Claude Rene Georg Blondel, 2 More », U.S. patent 3,875,156 (1975 to Rhone Poulenc Sa).

[19] [19]
Schussen, & Li Haixia, et al. CN 106568857 (2019 to YUEYANG XINHUADA PHARMACEUTICAL CO Ltd).

[Haddad_et_al_2015-20] [20]
Haddad P, Taylor M, Patel MX, Taylor D (June 2015). "Guidance on switching away from Piportil Depot® (pipotiazine palmitate) injection". The British Journal of Psychiatry. 206 (6): 521. doi:10.1192/bjp.206.6.521. PMID 26034183.

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[6]

[7]

[8]

[9]

[10]

[11]

[12]

[13]

[14]

[1]

[15]

[16]

[17]

[18]

[19]

[20]

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 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.

Pipotiazine

Pipotiazine

Medical uses

Contraindications

Pharmacokinetics

Synthesis

History

References

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