Periciazine

Periciazine (INN), also known as pericyazine (BAN) or propericiazine, is a drug that belongs to the phenothiazine class of typical antipsychotics.

Periciazine
Clinical data
Pregnancy
category
  • AU: C
Routes of
administration		Oral
Drug classTypical antipsychotic
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • In general: ℞ (Prescription only)
Pharmacokinetic data
MetabolismHepatic (mostly via conjugation)[1]
Elimination half-life12 h[1]
ExcretionRenal[1]
Identifiers
IUPAC name
  • 10-[3-(4-hydroxypiperidin-1-yl)propyl]-10H-phenothiazine-2-carbonitrile
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.018.248
Chemical and physical data
FormulaC21H23N3OS
Molar mass365.50 g·mol−1
3D model (JSmol)
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
 NY (what is this?)  (verify)

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.[2]

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.[1] A 2014 systematic review compared periciazine with typical antipsychotics for schizophrenia:

Periciazine versus typical antipsychotic for schizophrenia[3]
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.[3]

Periciazine has also been studied in the treatment of opioid dependence.[4]

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.[5] It has a relatively high risk of causing hyperprolactinaemia and a moderate risk of causing weight gain and orthostatic hypotension.[5]

Synthesis
Thieme Patent (Ex V):[6]

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
  1. "NEULACTIL PRODUCT INFORMATION" (PDF). TGA eBusiness Services. sanofi-aventis australia pty ltd. 13 September 2011. Retrieved 2 November 2013.
  2. Pericyazine. Martindale: The Complete Drug Reference. The Royal Pharmaceutical Society of Great Britain. 23 September 2011. Retrieved 2 November 2013.
  3. Matar HE, Almerie MQ, Makhoul S, Xia J, Humphreys P (May 2014). "Pericyazine for schizophrenia". The Cochrane Database of Systematic Reviews. 5 (5): CD007479. doi:10.1002/14651858.CD007479.pub2. PMID 24825770.
  4. 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.
  5. "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.
  6. FR1212031 idem Robert Jacques Georges, Jacob Robert Michel, U.S. Patent 3,075,976 (1963 to Rhone Poulenc Sa).
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