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Phenothiazines

Drugs & Medication

Phenothiazines

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Phenothiazine
Phenothiazine
General
Systematic name 10H-phenothiazine
Other names thiodiphenylamine, dibenzothiazine
Molecular formula C12H9NS
SMILES  ?
Molar mass 199.2762 g/mol
Appearance yellow rhombic leaflets or

diamond-shaped plates

CAS number 92-84-2
Properties
Density and phase  ? g/cm3, solid at STP
Soluble benzene, ether, hot acetic acid,
ethanol (slightly), mineral oil (slightly)
Insoluble water, petroleum ether, chloroform
Melting point 185 C
Boiling point 371 C
Acidity (pKa) approx 23 in DMSO
Except where noted otherwise, data are given for
materials in their standard state (at 25 C, 100 kPa)

Phenothiazine (a phenol derivative of thiazine) is a pesticide and industrial chemical used in pharmaceutical manufacturing. It is sometimes used as an antihelminthic. It was introduced by DuPont as an insecticide in 1935. It is now most commonly used as an intermediate chemical in the manufacture of various psychiatric drugs.

Phenothiazine-derivative drugs

The word "phenothiazines" is used to describe the largest of the five main classes of antipsychotic drugs. Although these drugs are generally effective, there are often serious side effects including tardive dyskinesia and sedation (especially in the early stages of treatment).

There are three groups of phenothiazines, differing by their chemical structure and their pharmacological effects:

Group Autonomic Example Sedative Extrapyramidal side-effect
Aliphatic compounds
moderate Chlorpromazine (Thorazine, Largactil) strong moderate
Promazine moderate moderate
Triflupromazine (Vesprin) strong moderate/strong
Levomepromazine (Nozinan) extremely strong low
Piperidines strong Mesoridazine strong weak
Thioridazine (Mellaril) strong weak
Piperazines weak Fluphenazine weak/moderate strong
Perphenazine weak/moderate strong
Prochlorperazine (Compazine, Stemetil)
Trifluoperazine (Stelazine) moderate strong


 

References

  1.   History of Insecticides and Control Equipment Clemson University Pesticide Information Program.
  2.   Hendricks, Christensen, J.B., and Kristiansen, Jette E. Sonderborg, Denmark. "Antibakterielle Eigenschaften der Phenothiazine: Eine Behandlungsoption fr die Zukunft?" Chemotherapie Journal. 13.5. (2004): 203205. Wissenschaftliche Verlagsgesesellschaft mbH. 21 August 2005. (PDF).

Home | Up | Atypical antipsychotics | Phenothiazines | Tardive dyskinesia | Typical antipsychotics | Lithium pharmacology

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