Structure via PubChem · Public domain (PubChem)
thioridazine
Sign in to saveAlso known as MEL269, thioridazin, TP-21, 10-[2-(1-methyl-2-piperidyl)ethyl]-2-methylsulfanyl-phenothiazine, 3-methylmercapto-N-[2′-(N-methyl-2-piperidyl)ethyl]phenothiazine, 2-methylmercapto-10-[2-(N-methyl-2-piperidyl)ethyl]phenothiazine
Thioridazine (sold under the brand names Mellaril or Melleril) is a first-generation antipsychotic drug belonging to the phenothiazine drug group and was previously widely used in the treatment of schizophrenia and psychosis. The branded product was withdrawn worldwide in 2005 because it caused severe cardiac arrhythmias. However, generic versions are still available in the United States.
Key facts
- Drug.PubChem
- 5452
- Drug.verifiedrevid
- 470608946
- Drug.IUPAC_name
- 10-{2-[(RS)-1-Methylpiperidin-2-yl]ethyl}-2-methylsulfanylphenothiazine
- Drug.image
- Thioridazine.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 200px
- Drug.image2
- Thioridazine ball-and-stick model from xtal 1975.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 250px
- Drug.MedlinePlus
- a682119
- Drug.DailyMedID
- Thioridazine
- Drug.licence_US
- Thioridazine
- Drug.pregnancy_AU
- C
- Drug.pregnancy_US
- N
- Drug.legal_BR
- C1
- Drug.legal_status
- Withdrawn by the manufacturer worldwide; generic formulations are still available by prescription
- Drug.routes_of_administration
- Oral
- Drug.class
- Typical antipsychotic
via Wikipedia infobox
Chemical data
- Formula
- C21H26N2S2
- Molecular weight
- 370.6 g/mol
- IUPAC name
- 10-[2-(1-methylpiperidin-2-yl)ethyl]-2-methylsulfanylphenothiazine
- SMILES
- CN1CCCCC1CCN2C3=CC=CC=C3SC4=C2C=C(C=C4)SC
- InChIKey
- KLBQZWRITKRQQV-UHFFFAOYSA-N
- XLogP
- 5.9
- Polar surface area
- 57.1 Ų
- H-bond donors
- 0
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
3,351 papers- Thioridazine.Tuberculosis (Edinburgh, Scotland) · 2008
- Thioridazine for dementia.The Cochrane database of systematic reviews · 2001
- Thioridazine for schizophrenia.The Cochrane database of systematic reviews · 2007
- Thioridazine for schizophrenia.The Cochrane database of systematic reviews · 2000
- Thioridazine for dementia.The Cochrane database of systematic reviews · 2000
via PubMed
Wikidata facts
- Mass
- 370.153741
Show 5 more facts
- chemical formula
- C₂₁H₂₆N₂S₂
- canonical SMILES
- CN1CCCCC1CCN2C3=CC=CC=C3SC4=C2C=C(C=C4)SC
- World Health Organisation international non-proprietary name
- thioridazine
- Commons category
- Thioridazine
- defined daily dose
- 0.3
via Wikidata · CC0
~10 min read
Article
10 sectionsContents
- Indications
- Side effects
- Pharmacology
- Metabolism
- History
- Antimicrobial activity
- Synthesis
- References
- Further reading
- External links
{{Infobox drug | verifiedrevid = 470608946 | IUPAC_name = 10-{2-[(RS)-1-Methylpiperidin-2-yl]ethyl}-2-methylsulfanylphenothiazine | image = Thioridazine.svg | image_class = skin-invert-image | width = 200px | image2 = Thioridazine ball-and-stick model from xtal 1975.png | image_class2 = bg-transparent | width2 = 250px
| Drugs.com = | MedlinePlus = a682119 | DailyMedID = Thioridazine | licence_US = Thioridazine | pregnancy_AU = C | pregnancy_US = N | legal_AU = | legal_BR = C1 | legal_BR_comment = | legal_CA = | legal_DE = | legal_NZ = | legal_UK = | legal_US = | legal_EU = | legal_UN = | legal_status = Withdrawn by the manufacturer worldwide; generic formulations are still available by prescription | routes_of_administration = Oral | class = Typical antipsychotic