Tiotixene

Tiotixene
Clinical data
Trade namesNavane
Other namesThiothixene (USAN US)
AHFS/Drugs.comMonograph
MedlinePlusa682867
Pregnancy
category
  • AU: B1
Routes of
administration		By mouth
Drug classTypical antipsychotic
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C1 (Other controlled substances)[1]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability~100%
MetabolismHepatic
Elimination half-life10–20 hours
ExcretionGastrointernal tract, faeces
Identifiers
  • (9Z)-N,N-dimethyl-9-[3-(4-methylpiperazin-1-yl)propylidene]-9H-thioxanthene-2-sulfonamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.233.356 Edit this at Wikidata
Chemical and physical data
FormulaC23H29N3O2S2
Molar mass443.62 g·mol−1
3D model (JSmol)
  • O=S(=O)(N(C)C)c2cc1C(\c3c(Sc1cc2)cccc3)=C/CCN4CCN(C)CC4
  • InChI=1S/C23H29N3O2S2/c1-24(2)30(27,28)18-10-11-23-21(17-18)19(20-7-4-5-9-22(20)29-23)8-6-12-26-15-13-25(3)14-16-26/h4-5,7-11,17H,6,12-16H2,1-3H3/b19-8- checkY
  • Key:GFBKORZTTCHDGY-UWVJOHFNSA-N checkY
  (verify)

Tiotixene, or thiothixene is a typical antipsychotic agent currently sold under the brand name Navane which is predominantly utilised to treat acute and chronic schizophrenia.[2] Beyond its primary indication, it can exhibit a variety of effects common to neuroleptic drugs including anxiolytic, anti-depressive, and anti-aggressive properties.[3]

The drug was first synthesized and marketed in 1967 under the pharmaceutical company Pfizer.[2][4][5][6] While the usage of the drug has declined in recent decades, the drug continues to be manufactured and prescribed in the US and Canada.[6]

Being a member of the thioxanthene class, it is chemically related to other typical neuroleptic agents such as chlorprothixene, clopenthixol, flupenthixol, and zuclopenthixol. Tiotixene also shares structural similarities with thioproperazine and pipotiazine, which are members of the phenothiazine class.

  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.
  2. ^ a b Wyatt DK, Grady LT (1990-01-01). "Thiothixene". In Florey K, Al-Badr AA, Forcier GA, Brittain HG (eds.). Analytical Profiles of Drug Substances. Vol. 18. Academic Press. pp. 527–565. doi:10.1016/s0099-5428(08)60680-2. ISBN 978-0-12-260818-6.
  3. ^ Mann JJ (2009-08-03). "Before Prozac: The troubled history of mood disorders in psychiatry". The Journal of Clinical Investigation. 119 (8): 2117. doi:10.1172/JCI40286. ISSN 0021-9738. PMC 2719946.
  4. ^ Poulsen MØ, Dastidar SG, Roy DS, Palchoudhuri S, Kristiansen JE, Fey SJ (December 2021). "A Double-Edged Sword: Thioxanthenes Act on Both the Mind and the Microbiome". Molecules. 27 (1): 196. doi:10.3390/molecules27010196. PMC 8746497. PMID 35011432.
  5. ^ William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia. Elsevier. pp. 3214–. ISBN 978-0-8155-1856-3.
  6. ^ a b Eslami Shahrbabaki M, Dehnavieh R, Vali L, Sharafkhani R, et al. (Cochrane Schizophrenia Group) (October 2018). "Chlorpromazine versus piperacetazine for schizophrenia". The Cochrane Database of Systematic Reviews. 10 (10): CD011709. doi:10.1002/14651858.CD012790. PMC 6483621. PMID 30378678.