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Thioproperazine

Typical antipsychotic medication

Thioproperazine
Summary

Typical antipsychotic medication

FieldValue
drug_nameThioproperazine
imageThioproperazine.svg
image_classskin-invert-image
width240
altChemical structure of Thioproperazine
tradenameMajeptil
ATC_prefixN05
ATC_suffixAB08
legal_AU
legal_BRC1
legal_BR_comment
legal_CA
legal_DE
legal_NZ
legal_UK
legal_US
legal_UN
CAS_number316-81-4
PubChem9429
DrugBankDB01622
ChemSpiderID9058
UNIIYJ050AQ56X
KEGGD08585
ChEBI59120
ChEMBL609109
IUPAC_nameN,N-dimethyl-10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine-2-carboxamide
C22H=30N=4O=2S=2
SMILESCN1CCN(CC1)CCCN2C3=CC=CC=C3SC4=C2C=C(C=C4)S(=O)(=O)N(C)C
StdInChI1S/C22H30N4O2S2/c1-23(2)30(27,28)18-9-10-22-20(17-18)26(19-7-4-5-8-21(19)29-22)12-6-11-25-15-13-24(3)14-16-25/h4-5,7-10,17H,6,11-16H2,1-3H3
StdInChIKeyVZYCZNZBPPHOFY-UHFFFAOYSA-N

| Drugs.com =

| elimination_half-life =

Thioproperazine, sold under the brand name Majeptil, is a typical antipsychotic of the phenothiazine group which is used as a tranquilizer, antiemetic, sedative, and in the treatment of schizophrenia and manic phase of bipolar disorder. Majeptil is available in 10 mg tablets.

Side effects

Common

  • Extrapyramidal symptoms
  • Amenorrhea
  • Decreased sexual interest and/or function
  • Swelling of breasts and milk production in males and females
  • Difficulty sleeping
  • Constipation
  • Reduced amount of urine
  • Dizziness
  • Drowsiness
  • Dry mouth
  • Nausea
  • Headache
  • Weight changes

Rare but potentially serious adverse effects

  • Agranulocytosis
  • Neuroleptic Malignant Syndrome (NMS)
  • Sudden cardiac death
  • Torsades de pointes

Elderly individuals with dementia-related psychosis treated with antipsychotic medication are at an increased risk of death compared to individuals not receiving antipsychotics.

Drug interactions

Medications for allergies (e.g., Benadryl diphenhydramine), certain medications for sleep (e.g., lorazepam, zopiclone), certain medications for pain (e.g., fentanyl), and Antiparkinson medications can increase the sedative effect of thioproperazine and can be potentially dangerous when used together.

Synthesis

1088964}} (1960 to Rhone Poulenc Sa).</ref>

Thioether formation between 2-Aminothiophenol (1) and 4-Chloro-N,N-Dimethyl-3-Nitrobenzenesulfonamide [137-47-3] (2) gives 4-(2-aminophenyl)sulfanyl-N,N-dimethyl-3-nitrobenzenesulfonamide [5510-56-5] (3). Sandmeyer reaction with cuprous bromide [7787-70-4] gave 4-[(2-Bromophenyl)-thio]-N,N'-dimethyl-3-nitro-benzenesulfonamide [5510-58-7] (4). Bechamp reduction gave 3-Amino-4-((2-bromophenyl)thio)-N,N-dimethylbenzenesulphonamide [5592-64-3] (5). Goldberg reaction completed the formation of the phenothiazine ring and gave N,N-dimethyl-10H-phenothiazine-2-sulfonamide [1090-78-4] (6). Attachment of the sidechain by sodamide reaction with 1-(3-Chloropropyl)-4-Methylpiperazine [104-16-5] (7) completes the synthesis of Thioproperazine (8), respectively.

References

References

  1. Anvisa. (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial". [[Diário Oficial da União]].
  2. (2000). "Index Nominum 2000: International Drug Directory". Taylor & Francis.
  3. (6 December 2012). "Concise Dictionary of Pharmacological Agents: Properties and Synonyms". Springer Science & Business Media.
  4. "Phenothiazines (Systemic)". Drugs.com.
  5. "Thioproperazine - Oral".
  6. "Thioproperazine".
  7. "Schizophrenia Society of Ontario - Majeptil (thioproperazine)".
  8. (1974). "Synthesis and comparison of activity of 2- and 3-dimethylsulfamidophenothiazine derivatives". Pharmaceutical Chemistry Journal.
  9. , {{Cite patent. GB. 814512 (1959 to Rhone Poulenc SA).
  10. , {{Cite patent. GB. 813025 (1959-05-06 to Rhone Poulenc Sa).
  11. Robert Michel Jacob, Gilbert Louis Regnier, {{Cite patent. DE. 1088964 (1960 to Rhone Poulenc Sa).
Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

phenothiazines 4-methylpiperazin-1-yl-compounds sulfonamides typical-antipsychotics
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