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Perazine

From Wikipedia, the free encyclopedia
Typical antipsychotic medication
Not to be confused withPerzine.
Pharmaceutical compound
Perazine
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • 10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine
CAS Number
PubChemCID
DrugBank
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UNII
KEGG
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ECHA InfoCard100.001.435Edit this at Wikidata
Chemical and physical data
FormulaC20H25N3S
Molar mass339.50 g·mol−1
3D model (JSmol)
  • CN1CCN(CC1)CCCN2C3=CC=CC=C3SC4=CC=CC=C42
  • InChI=1S/C20H25N3S/c1-21-13-15-22(16-14-21)11-6-12-23-17-7-2-4-9-19(17)24-20-10-5-3-8-18(20)23/h2-5,7-10H,6,11-16H2,1H3 ☒N
  • Key:WEYVCQFUGFRXOM-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Perazine (Taxilan) is a moderate-potencytypical antipsychotic of thephenothiazine class. It is quite similar tochlorpromazine, and acts as adopamine antagonist. It was very popular in West-Germany. A 2014systematic review compared it with other antipsychotic drugs:

Perazine versus other antipsychotic drugs for schizophrenia[1]
Summary
The number, size and reporting ofrandomized controlled perazine trials are insufficient to present firm conclusions about the properties of thisantipsychotic. It is possible that perazine is associated with a similar risk ofextrapyramidal side effects as someatypical antipsychotics but this is based on few comparisons of limited power.[1]
OutcomeFindings in wordsFindings in numbersQuality of evidence
Global state
No better or deterioration
Follow-up: average 5 weeks		Perazine may decrease the chance of experiencing this outcome. These findings are based on data of low quality.RR 0.43 (0.23 to 0.81)Low
Mental state
Less than 30% BPRS reduction
Follow-up: mean 5 weeks		The average overall mental state score in the perazine group was lower than for those given other antipsychotic drugs but the difference between the groups was not clear. These findings are based on data of low quality.RR 0.82 (0.61 to 1.09)Low
Adverse effects
Needing antiparkinson medication
Follow-up: average 5 weeks		Perazine might increase the risk of experiencing this outcome but at present it is not possible to be confident about the difference between perazine and other antipsychotic drugs. Data supporting this finding are very limited.RR 4.5 (1.04 to 19.45)Very low
Leaving the study early - due to adverse events
Follow-up: average 4 weeks		There was not a clear difference between perazine and the other antipsychotic drugs for this general outcome reflecting overall adverse event 'load'. These findings are based on data of low quality.0.87 (0.4 to 1.9)Low
Acceptability of treatment
Leaving the studies early - any reason
Follow-up: 5 weeks		Perazine and the comparison antipsychotic drugs were equally tolerated. These findings are based on data of low quality.RR 0.62 (0.35 to 1.1)Low
No study reported any data on outcomes such asquality of life or information relating tosatisfaction with care.

Synthesis

[edit]
Perazine synthesis:[2][3] Patents:[4][5] Alternate source:[6][7]

Phenothiazine-10-propionitrile [1698-80-2] (1) is treated with a mixture of acid and alcohol giving Methyl phenothiazinepropionate,CID:368244 (2). Heating with1-methylpiperazine (3) gives the amide [91508-47-3] (4). Reduction of this last by means ofdiborane yieldsPerazine (5).

See also

[edit]

References

[edit]
  1. ^abLeucht S, Helfer B, Hartung B (January 2014)."Perazine for schizophrenia".The Cochrane Database of Systematic Reviews.1 (1): CD002832.doi:10.1002/14651858.CD002832.pub3.PMC 11015532.PMID 24425538.
  2. ^Hromatka, O.; Sauter, F.; Schlager, L. H. (1957). "Untersuchungen über Phenthiazinderivate III: Über die Synthese von 10-(Piperazinoalkyl)-phenthiazinen". Monatshefte für Chemie. 88 (2): 193–201. doi:10.1007/BF00901625.
  3. ^Hromatka, O.; Stehlik, G.; Sauter, F. (1960). "Untersuchungen über Phenthiazinderivate, 12. Mitt.: Reaktionen zur Géwinnung von 10-(?-Methylpiperazinylpropyl)-phenthiazin". Monatshefte für Chemie 91 (1): 107–116. doi:10.1007/BF00903173.
  4. ^GB780193 idem Horclois Raymond Jacques,U.S. patent 2,902,485 (1957 toRhône-Poulenc).
  5. ^Anon.,GB 901187  (1962 to Chemische Fabrik Promonta GmbH).
  6. ^Owen, Terence C. (1984). "Synthesis of perazine". Journal of Heterocyclic Chemistry. 21 (1): 265–266. doi:10.1002/jhet.5570210154.
  7. ^Brufani; Cesta; Filocamo; Lappa; Marta; Pomponi; Meroni; Pagella Farmaco, 1992, vol. 47, # 5 p. 585 – 597.

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