Thioproperazine

Thioproperazine
Clinical data
Trade names	Majeptil
ATC code	N05AB08 (WHO) ;
Legal status
Legal status	BR: Class C1 (Other controlled substances);
Identifiers
	IUPAC name N,N-dimethyl-10--10H-phenothiazine-2-carboxamide;
CAS Number	316-81-4;
PubChem CID	9429;
DrugBank	DB01622;
ChemSpider	9058;
UNII	YJ050AQ56X;
KEGG	D08585;
ChEBI	CHEBI:59120;
ChEMBL	ChEMBL609109;
CompTox Dashboard (EPA)	DTXSID1023655 ;
ECHA InfoCard	100.005.695
Chemical and physical data
Formula	C22H30N4O2S2
Molar mass	446.63 g·mol−1
3D model (JSmol)	Interactive image;
	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;

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.^[2]^[3]^[4]^[5] Majeptil is available in 10 mg tablets.^[6]

Side effects

Common^[7]

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

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

Thioether formation between 2-Aminothiophenol (1) and 4-Chloro-N,N-Dimethyl-3-Nitrobenzenesulfonamide (2) gives 4-(2-aminophenyl)sulfanyl-N,N-dimethyl-3-nitrobenzenesulfonamide (3). Sandmeyer reaction with cuprous bromide gave 4--N,N'-dimethyl-3-nitro-benzenesulfonamide (4). Bechamp reduction gave 3-Amino-4-((2-bromophenyl)thio)-N,N-dimethylbenzenesulphonamide (5). Goldberg reaction completed the formation of the phenothiazine ring and gave N,N-dimethyl-10H-phenothiazine-2-sulfonamide (6). Attachment of the sidechain by sodamide reaction with 1-(3-Chloropropyl)-4-Methylpiperazine (7) completes the synthesis of Thioproperazine (8), respectively.

References

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 1019–. ISBN 978-3-88763-075-1.
^ 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.
^ "Phenothiazines (Systemic)". Drugs.com.
^ "Thioproperazine - Oral". Retrieved 2018-09-16.
^ "Thioproperazine". www.drugbank.ca. Retrieved 2018-09-16.
^ "Schizophrenia Society of Ontario - Majeptil (thioproperazine)". www.schizophrenia.on.ca. Retrieved 2018-09-16.
^ Shavyrina VV, Zhuravlev SV, Vikhlyaev YI, Klygul' TA, Slyn'ko ÉI (1974). "Synthesis and comparison of activity of 2- and 3-dimethylsulfamidophenothiazine derivatives". Pharmaceutical Chemistry Journal. 8 (5): 286–290. doi:10.1007/BF00771334. S2CID 22229797.
^ , GB 814512 (1959 to Rhone Poulenc SA).
^ , GB 813025 (1959-05-06 to Rhone Poulenc Sa).
^ Robert Michel Jacob, Gilbert Louis Regnier, DE 1088964 (1960 to Rhone Poulenc Sa).

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[1] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[IndexNominum2000-2] Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 1019–. ISBN 978-3-88763-075-1.

[MortonHall2012-3] 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.

[Drugs.com-4] "Phenothiazines (Systemic)". Drugs.com.

[5] "Thioproperazine - Oral". Retrieved 2018-09-16.

[6] "Thioproperazine". www.drugbank.ca. Retrieved 2018-09-16.

[7] "Schizophrenia Society of Ontario - Majeptil (thioproperazine)". www.schizophrenia.on.ca. Retrieved 2018-09-16.

[8] Shavyrina VV, Zhuravlev SV, Vikhlyaev YI, Klygul' TA, Slyn'ko ÉI (1974). "Synthesis and comparison of activity of 2- and 3-dimethylsulfamidophenothiazine derivatives". Pharmaceutical Chemistry Journal. 8 (5): 286–290. doi:10.1007/BF00771334. S2CID 22229797.

[9] , GB 814512 (1959 to Rhone Poulenc SA).

[10] , GB 813025 (1959-05-06 to Rhone Poulenc Sa).

[11] Robert Michel Jacob, Gilbert Louis Regnier, DE 1088964 (1960 to Rhone Poulenc Sa).

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v t e Antipsychotics (N05A)
Typical	Butyrophenones: Benperidol Bromperidol Bromperidol decanoate Droperidol Haloperidol^# Haloperidol decanoate Moperone Pipamperone Spiperone Timiperone Trifluperidol Diphenylbutylpiperidines: Fluspirilene Penfluridol Pimozide Phenothiazines: Acepromazine Acetophenazine Butaperazine Carphenazine (carfenazine)^‡ Chlorpromazine Cyamemazine Dixyrazine Fluphenazine Fluphenazine decanoate Fluphenazine enanthate Levomepromazine (methotrimeprazine) Mesoridazine Perazine Periciazine Perphenazine BL-1020 Perphenazine decanoate Perphenazine enanthate Piperacetazine Pipotiazine Pipotiazine palmitate Pipotiazine undecylenate Prochlorperazine Promazine Sulforidazine Thiopropazate Thioproperazine Thioridazine Trifluoperazine Triflupromazine Thioxanthenes: Chlorprothixene Clopenthixol Clopenthixol decanoate Flupentixol Flupentixol decanoate Tiotixene (thiothixene) Zuclopenthixol Zuclopenthixol acetate Zuclopenthixol decanoate
Disputed	Benzamides: Amisulpride Levosulpiride Nemonapride Remoxipride^‡ Sulpiride Sultopride Tiapride Veralipride^‡ Butyrophenones: Melperone Tricyclics: Carpipramine Clocapramine Clorotepine Clotiapine Loxapine Mosapramine Oxyprothepin decanoate Others: Molindone
Atypical	Benzisoxazole/benzisothiazoles: Iloperidone Lurasidone Paliperidone Paliperidone palmitate Perospirone Risperidone^# Ziprasidone Butyrophenones: Lumateperone Phenylpiperazines/quinolinones: Aripiprazole Aripiprazole lauroxil Brilaroxazine^† Brexpiprazole Cariprazine Tricyclics: Asenapine Clozapine^# Olanzapine (+samidorphan) Quetiapine Zotepine Others: Blonanserin Pimavanserin Sertindole
Others	Monoamine-depleting agents: Oxypertine Reserpine Tetrabenazine Others/unknown: Azacyclonol
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III