Periciazine

Periciazine
Clinical data
Pregnancy; category	AU: C; ;
Routes of; administration	Oral
Drug class	Typical antipsychotic
ATC code	N05AC01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); CA: ℞-only; UK: POM (Prescription only); In general: ℞ (Prescription only);
Pharmacokinetic data
Metabolism	Hepatic (mostly via conjugation)
Elimination half-life	12 h
Excretion	Renal
Identifiers
	IUPAC name 10-[3-(4-hydroxypiperidin-1-yl)propyl]-10H-phenothiazine-2-carbonitrile;
CAS Number	2622-26-6 ;
PubChem CID	4747;
DrugBank	DB01608 ;
ChemSpider	4585 ;
UNII	3405M6FD73;
KEGG	D01485 ;
ChEBI	CHEBI:31981 ;
ChEMBL	ChEMBL251940 ;
CompTox Dashboard (EPA)	DTXSID5045910 ;
ECHA InfoCard	100.018.248
Chemical and physical data
Formula	C21H23N3OS
Molar mass	365.50 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CN(CCC1O)CCCN2C3=CC=CC=C3SC4=C2C=C(C=C4)C#N;
	InChI InChI=1S/C21H23N3OS/c22-15-16-6-7-21-19(14-16)24(18-4-1-2-5-20(18)26-21)11-3-10-23-12-8-17(25)9-13-23/h1-2,4-7,14,17,25H,3,8-13H2 ; Key:LUALIOATIOESLM-UHFFFAOYSA-N ;
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Periciazine (INN), also known as pericyazine (BAN) or propericiazine, is a drug that belongs to the phenothiazine class of typical antipsychotics.

Periciazine is not approved for sale in the United States. It is commonly sold in Canada, Italy and Russia under the tradename Neuleptil and in United Kingdom and Australia under the tradename Neulactil.^[3]

Medical uses

The primary uses of periciazine include in the short-term treatment of severe anxiety or tension and in the maintenance treatment of psychotic disorders such as schizophrenia. There is insufficient evidence to determine whether periciazine is more or less effective than other antipsychotics.^[2] A 2014 systematic review compared periciazine with typical antipsychotics for schizophrenia:

Periciazine versus typical antipsychotic for schizophrenia^[4]

Summary

On the basis of very low quality evidence it is not possible to determine the effects of periciazine in comparison with antipsychotics such as chlorpromazine or trifluoperazine for the treatment of schizophrenia. There is some evidence, however, that periciazine may be associated with a higher incidence of extrapyramidal side effects than other antipsychotics.^[4]

Outcome	Findings in words	Findings in numbers	Quality of evidence
Global state
Not improved Follow-up: 6-12 weeks	Periciazine may increase the risk of being 'not improved', but, at present it is not possible to be confident about the difference between people receiving periciazine and those given chlorpromazine or trifluoperazine. Data supporting this finding are very limited.	RR 1.24 (0.93 to 1.66)	Very low
Adverse events
Extrapyramidal side effect Follow-up: 6-12 weeks	Periciazine may reduce the chance of experiencing the movement disorder, compared with chlorpromazine or trifluoperazine, but, at present there is only very limited data supporting this finding.	RR 0.59 (0.38 to 0.89)	Very low
Leaving the study early
For any reasons Follow-up: 9-12 weeks	Periciazine may reduce the chance of leaving the study early, but, at present it is not possible to be confident about the difference between the two treatments and data supporting this finding are very limited.	RR 0.46 (0.11 to 1.9)	Very low
Missing outcomes
	No study reported any data on outcomes such as relapse, mental state, cost-effectiveness, and information relating to behavior

Periciazine has also been studied in the treatment of opioid dependence.^[5]

Adverse effects

Periciazine is a rather sedating and anticholinergic antipsychotic, and despite being classed with the typical antipsychotics, its risk of extrapyramidal side effects is comparatively low.^[6] It has a relatively high risk of causing hyperprolactinaemia and a moderate risk of causing weight gain and orthostatic hypotension.^[6]

Synthesis

Thieme Patent (Ex V):^[7]

The final step in the synthesis involves the alkylation of 3-(2-cyanophenothiazin-10-yl)propyl 4-methylbenzenesulfonate, CID:134990672 (1) with 4-Piperidinol [5382-16-1] (2) giving Periciazine (3).

References

^ 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.
^ ^a ^b ^c ^d "NEULACTIL PRODUCT INFORMATION" (PDF). TGA eBusiness Services. sanofi-aventis australia pty ltd. 13 September 2011. Retrieved 2 November 2013.
^ Pericyazine. The Royal Pharmaceutical Society of Great Britain. 23 September 2011. Retrieved 2 November 2013. {{cite book}}: |work= ignored (help)
^ ^a ^b Matar HE, Almerie MQ, Makhoul S, Xia J, Humphreys P (May 2014). "Pericyazine for schizophrenia". The Cochrane Database of Systematic Reviews. 2014 (5): CD007479. doi:10.1002/14651858.CD007479.pub2. PMC 11023599. PMID 24825770.
^ Sivolap IuP, Savchenkov VA (1999). "[The use of neuroleptics in treating opiate dependence]". Zhurnal Nevrologii I Psikhiatrii imeni S.S. Korsakova (in Russian). 99 (6): 29–34. PMID 10441864.
^ ^a ^b "Approximate relative frequency (not intensity) of common adverse effects of antipsychotics (Table 8.21) [NB1]". eTherapeutic Guidelines complete. Therapeutic Guidelines Limited. February 2013. Retrieved 2 November 2013.^{[permanent dead link‍]}
^ FR1212031 idem Robert Jacques Georges, Jacob Robert Michel, U.S. patent 3,075,976 (1963 to Rhone Poulenc Sa).

External links

Neulactil - Summary of Product Characteristics from the electronic Medicines Compendium
[1] from the Therapeutic Goods Administration.
[2] from Health Canada.

[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.

[TGA-2] "NEULACTIL PRODUCT INFORMATION" (PDF). TGA eBusiness Services. sanofi-aventis australia pty ltd. 13 September 2011. Retrieved 2 November 2013.

[Martindale-3] Pericyazine. The Royal Pharmaceutical Society of Great Britain. 23 September 2011. Retrieved 2 November 2013. {{cite book}}: |work= ignored (help)

[Mat2014-4] Matar HE, Almerie MQ, Makhoul S, Xia J, Humphreys P (May 2014). "Pericyazine for schizophrenia". The Cochrane Database of Systematic Reviews. 2014 (5): CD007479. doi:10.1002/14651858.CD007479.pub2. PMC 11023599. PMID 24825770.

[pmid10441864-5] Sivolap IuP, Savchenkov VA (1999). "[The use of neuroleptics in treating opiate dependence]". Zhurnal Nevrologii I Psikhiatrii imeni S.S. Korsakova (in Russian). 99 (6): 29–34. PMID 10441864.

[eTG-6] "Approximate relative frequency (not intensity) of common adverse effects of antipsychotics (Table 8.21) [NB1]". eTherapeutic Guidelines complete. Therapeutic Guidelines Limited. February 2013. Retrieved 2 November 2013.^{[permanent dead link‍]}

[7] FR1212031 idem Robert Jacques Georges, Jacob Robert Michel, U.S. patent 3,075,976 (1963 to Rhone Poulenc Sa).

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Clinical data

Pregnancy category	AU: C
Routes of administration	Oral
Drug class	Typical antipsychotic
ATC code	N05AC01 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) BR: Class C1 (Other controlled substances)^[1] CA: ℞-only UK: POM (Prescription only) In general: ℞ (Prescription only)
Pharmacokinetic data
Metabolism	Hepatic (mostly via conjugation)^[2]
Elimination half-life	12 h^[2]
Excretion	Renal^[2]
Identifiers
IUPAC name 10-[3-(4-hydroxypiperidin-1-yl)propyl]-10H-phenothiazine-2-carbonitrile
CAS Number	2622-26-6^Y
PubChem CID	4747
DrugBank	DB01608^N
ChemSpider	4585^N
UNII	3405M6FD73
KEGG	D01485^Y
ChEBI	CHEBI:31981^N
ChEMBL	ChEMBL251940^N
CompTox Dashboard (EPA)	DTXSID5045910
ECHA InfoCard	100.018.248
Chemical and physical data
Formula	C₂₁H₂₃N₃OS
Molar mass	365.50 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1CN(CCC1O)CCCN2C3=CC=CC=C3SC4=C2C=C(C=C4)C#N
InChI InChI=1S/C21H23N3OS/c22-15-16-6-7-21-19(14-16)24(18-4-1-2-5-20(18)26-21)11-3-10-23-12-8-17(25)9-13-23/h1-2,4-7,14,17,25H,3,8-13H2^N Key:LUALIOATIOESLM-UHFFFAOYSA-N^N
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