Perazine: Difference between revisions

{{Short description|Typical antipsychotic medication}}

{{Distinguish|Perzine}}

{{Infobox drug

| Verifiedfields = changed

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| verifiedrevid = 444044065

| image = Perazine.svg

<!--Clinical data-->

| tradename =

| Drugs.com = {{drugs.com|international|perazine}}

| pregnancy_category =

| legal_status =

| ATC_prefix = N05

| ATC_suffix = AB10

<!--Pharmacokinetic data-->

| bioavailability =

| protein_bound =

| metabolism =

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<!--Identifiers-->

| CAS_number = 84-97-9

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_supplemental =

| PubChem = 4744

| IUPHAR_ligand =

| DrugBank = DB12710

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| ChemSpiderID = 4582

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| UNII = 8915147A2B

| UNII_Ref = {{fdacite|correct|FDA}}

| KEGG = C16903

| ChEBI = 59118

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1697766

<!--Chemical data-->

| IUPAC_name = 10-[3-(4-methylpiperazin-1-yl)propyl]-10''H''-phenothiazine

| C=20 | H=25 | N=3 | S=1

| smiles = CN1CCN(CC1)CCCN2C3=CC=CC=C3SC4=CC=CC=C42

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = WEYVCQFUGFRXOM-UHFFFAOYSA-N

'''Perazine''' ('''Taxilan''') is a moderate-potency [[typical antipsychotic]] of the [[phenothiazine]] class. It is quite similar to [[chlorpromazine]], and acts as a [[dopamine antagonist]]. A 2014 [[systematic review]] compared it with other antipsychotic drugs:

{| class="wikitable"

|+ Perazine versus other antipsychotic drugs for schizophrenia<ref name=Leu2014>{{cite journal | vauthors = Leucht S, Helfer B, Hartung B | title = Perazine for schizophrenia | journal = The Cochrane Database of Systematic Reviews | volume = 1 | issue = 1 | pages = CD002832 | date = January 2014 | pmid = 24425538 | url = http://www.cochrane.org/CD002832/SCHIZ_perazine-for-schizophrenia | doi = 10.1002/14651858.CD002832.pub3 | pmc = 11015532 }}</ref>

|-

! Summary

|-

| The number, size and reporting of [[Randomized controlled trial|randomized controlled perazine trials]] are insufficient to present firm conclusions about the properties of this [[antipsychotic]]. It is possible that perazine is associated with a similar risk of [[Extrapyramidal symptoms|extrapyramidal]] side effects as some [[atypical antipsychotic]]s but this is based on few comparisons of limited power.<ref name=Leu2014/>

|-

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{| class="wikitable collapsible collapsed" style="width:100%;"

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! scope="col" style="text-align: left;"| Outcome

! scope="col" style="text-align: left;"| Findings in words

! scope="col" style="text-align: left;"| Findings in numbers

! scope="col" style="text-align: left;"| Quality of evidence

|-

! colspan="4" style="text-align: left;"| Global state

|-

| No better or deterioration<br>Follow-up: average 5 weeks|| Perazine may decrease the chance of experiencing this outcome. These findings are based on data of low quality.|| [[Relative risk|RR]] 0.43 (0.23 to 0.81) || [[The Grading of Recommendations Assessment, Development and Evaluation (GRADE) approach|Low]]

|-

! colspan="4" style="text-align: left;"| Mental state

|-

| Less than 30% BPRS reduction<br>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. || [[Relative risk|RR]] 0.82 (0.61 to 1.09) || [[The Grading of Recommendations Assessment, Development and Evaluation (GRADE) approach|Low]]

|-

! colspan="4" style="text-align: left;"| Adverse effects

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| Needing antiparkinson medication<br>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. || [[Relative risk|RR]] 4.5 (1.04 to 19.45) || [[The Grading of Recommendations Assessment, Development and Evaluation (GRADE) approach|Very low]]

|-

|Leaving the study early - due to adverse events<br>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) || [[The Grading of Recommendations Assessment, Development and Evaluation (GRADE) approach|Low]]

|-

! colspan="4" style="text-align: left;"| Acceptability of treatment

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| Leaving the studies early - any reason<br>Follow-up: 5 weeks || Perazine and the comparison antipsychotic drugs were equally tolerated. These findings are based on data of low quality.|| [[Relative risk|RR]] 0.62 (0.35 to 1.1) || [[The Grading of Recommendations Assessment, Development and Evaluation (GRADE) approach|Low]]

|-

| || No study reported any data on outcomes such as [[quality of life]] or information relating to [[Patient satisfaction|satisfaction with care]]. || ||

|}

|}

==Synthesis==

[[File:Perazine synthesis.svg|thumb|center|501px|Perazine synthesis:<ref>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.</ref><ref>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.</ref> Patents:<ref>GB780193 idem Horclois Raymond Jacques, {{US patent|2902485}} (1957 to [[Rhône-Poulenc]]).</ref><ref>Anon., {{Cite patent|GB|901187}} (1962 to Chemische Fabrik Promonta GmbH).</ref> Alternate source:<ref>Owen, Terence C. (1984). "Synthesis of perazine". Journal of Heterocyclic Chemistry. 21 (1): 265–266. doi:10.1002/jhet.5570210154.</ref><ref>Brufani; Cesta; Filocamo; Lappa; Marta; Pomponi; Meroni; Pagella Farmaco, 1992, vol. 47, # 5 p. 585 – 597.</ref>]]

Phenothiazine-10-propionitrile [1698-80-2] ('''1''') is treated with a mixture of acid and alcohol giving Methyl phenothiazinepropionate, [https://pubchem.ncbi.nlm.nih.gov/compound/368244 CID:368244] ('''2'''). Heating with [[1-methylpiperazine]] ('''3''') gives the amide [91508-47-3] ('''4'''). Reduction of this last by means of [[diborane]] yields ''Perazine'' ('''5''').

== See also ==

*[[Carphenazine]]

*[[Dixyrazine]]

*[[Methdilazine]]

*[[Pipamazine]]

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[[Category:Typical antipsychotics]]