perazine

{{Short description|Typical antipsychotic medication}}

{{Distinguish|Perzine}}

{{Infobox drug

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 444044065

| image = Perazine.svg

| tradename =

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

| pregnancy_category =

| legal_status =

| routes_of_administration =

| ATC_prefix = N05

| ATC_suffix = AB10

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

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| 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

| IUPAC_name = 10-[3-(4-methylpiperazin-1-yl)propyl]-10H-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. It was very popular in West-Germany. A 2014 systematic review compared it with other antipsychotic drugs:

class="wikitable"

|+ Perazine versus other antipsychotic drugs for schizophrenia{{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 }}

Summary
The number, size and reporting of 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 side effects as some atypical antipsychotics but this is based on few comparisons of limited power.
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{| class="wikitable collapsible collapsed" style="width:100%;"

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
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
colspan="4" style="text-align: left;"| 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
colspan="4" style="text-align: left;"| 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
colspan="4" style="text-align: left;"| 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 as quality of life or information relating to satisfaction with care.

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Synthesis

File:Perazine synthesis.svg).Anon., {{Cite patent|GB|901187}} (1962 to Chemische Fabrik Promonta GmbH). Alternate source:Owen, Terence C. (1984). "Synthesis of perazine". Journal of Heterocyclic Chemistry. 21 (1): 265–266. doi:10.1002/jhet.5570210154.Brufani; Cesta; Filocamo; Lappa; Marta; Pomponi; Meroni; Pagella Farmaco, 1992, vol. 47, # 5 p. 585 – 597.]]

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

References

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