Tiotixene

Tiotixene
Clinical data
Trade names	Navane
Other names	Thiothixene (USAN US)
AHFS/Drugs.com	Monograph
MedlinePlus	a682867
Pregnancy; category	AU: B1;
Routes of; administration	By mouth
Drug class	Typical antipsychotic
ATC code	N05AF04 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	~100%
Metabolism	Hepatic
Elimination half-life	10–20 hours
Excretion	Gastrointernal tract, faeces
Identifiers
	IUPAC name (9Z)-N,N-dimethyl-9-[3-(4-methylpiperazin-1-yl)propylidene]-9H-thioxanthene-2-sulfonamide;
CAS Number	3313-26-6 ;
PubChem CID	941651;
IUPHAR/BPS	212;
DrugBank	DB01623 ;
ChemSpider	819430 ;
UNII	7318FJ13YJ;
KEGG	D00374;
ChEMBL	ChEMBL1201 ;
CompTox Dashboard (EPA)	DTXSID2091542 ;
ECHA InfoCard	100.233.356
Chemical and physical data
Formula	C23H29N3O2S2
Molar mass	443.62 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=S(=O)(N(C)C)c2cc1C(\c3c(Sc1cc2)cccc3)=C/CCN4CCN(C)CC4;
	InChI 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- ; Key:GFBKORZTTCHDGY-UWVJOHFNSA-N ;
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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. Beyond its primary indication, it can exhibit a variety of effects common to neuroleptic drugs including anxiolytic, anti-depressive, and anti-aggressive properties.

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

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.