Thioproperazine

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.[1][2][3][4] Majeptil is available in 10 mg tablets.[5]

Thioproperazine
Clinical data
Trade namesMajeptil
ATC code
Identifiers
IUPAC name
  • N,N-dimethyl-10-[3-(4-methylpiperazin-1-yl)propyl]phenothiazine-2-sulfonamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.005.695
Chemical and physical data
FormulaC22H30N4O2S2
Molar mass446.63 g·mol−1
3D model (JSmol)
SMILES
  • CN1CCN(CC1)CCCN2C3=CC=CC=C3SC4=C2C=C(C=C4)S(=O)(=O)N(C)C
InChI
  • InChI=1S/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
  • Key:VZYCZNZBPPHOFY-UHFFFAOYSA-N

Side effects

Common[6]

Rare but potentially serious adverse effects

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
Thieme Synthesis:[7] Patents (Ex 3):[8][9][10]

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
  1. Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 1019–. ISBN 978-3-88763-075-1.
  2. Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 272–. ISBN 978-94-011-4439-1.
  3. "Phenothiazines (Systemic)". Drugs.com.
  4. "Thioproperazine - Oral". Retrieved 2018-09-16.
  5. "Thioproperazine". www.drugbank.ca. Retrieved 2018-09-16.
  6. "Schizophrenia Society of Ontario - Majeptil (thioproperazine)". www.schizophrenia.on.ca. Retrieved 2018-09-16.
  7. Shavyrina, V. V.; Zhuravlev, S. V.; Vikhlyaev, Yu. I.; Klygul', T. A.; Slyn'ko, �. I. (1974). "Synthesis and comparison of activity of 2- and 3-dimethylsulfamidophenothiazine derivatives". Pharmaceutical Chemistry Journal. 8 (5): 286–290. doi:10.1007/BF00771334.
  8. , GB 814512 (1959 to Rhone Poulenc SA).
  9. , GB 813025 (1959-05-06 to Rhone Poulenc Sa).
  10. Robert Michel Jacob, Gilbert Louis Regnier, DE 1088964 (1960 to Rhone Poulenc Sa).



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