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Periciazine

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Periciazine
Periciazine.svg
Clinical data
Pregnancy
category
  • AU: C
Routes of
administration
Oral
Drug class Typical antipsychotic
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • 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
  • 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 InfoCard 100.018.248
Chemical and physical data
Formula C21H23N3OS
Molar mass 365.50 g·mol−1
3D model (JSmol)
  • C1CN(CCC1O)CCCN2C3=CC=CC=C3SC4=C2C=C(C=C4)C#N
  • 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
 ☒NcheckY (what is this?)  (verify)

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.

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

Periciazine versus typical antipsychotic for schizophrenia
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.

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

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

Synthesis

Thieme Patent (Ex V):

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).

External links


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