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(Z)-thiothixene

Structure via PubChem · Public domain (PubChem)

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(Z)-thiothixene

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Also known as cis-thiothixene, thiothixene

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

Key facts

Drug.verifiedrevid
470609114
Drug.IUPAC_name
(9Z)-N,N-dimethyl-9-[3-(4-methylpiperazin-1-yl)propylidene]-9H-thioxanthene-2-sulfonamide
Drug.image
Thiothixene.svg
Drug.image_class
skin-invert-image
Drug.width
225px
Drug.USAN
Thiothixene
Drug.tradename
Navane
Drug.MedlinePlus
a682867
Drug.pregnancy_AU
B1
Drug.legal_AU
S4
Drug.legal_BR
C1
Drug.legal_status
Rx-only
Drug.routes_of_administration
By mouth
Drug.class
Typical antipsychotic
Drug.bioavailability
~100%
Drug.metabolism
Hepatic
Drug.elimination_half life
10–20 hours
Drug.excretion
Gastrointernal tract, faeces

via Wikipedia infobox

Chemical data

Formula
C23H29N3O2S2
Molecular weight
443.6 g/mol
IUPAC name
(9Z)-N,N-dimethyl-9-[3-(4-methylpiperazin-1-yl)propylidene]thioxanthene-2-sulfonamide
SMILES
CN1CCN(CC1)CC/C=C\2/C3=CC=CC=C3SC4=C2C=C(C=C4)S(=O)(=O)N(C)C
InChIKey
GFBKORZTTCHDGY-UWVJOHFNSA-N
XLogP
3.8
Polar surface area
77.5 Ų
H-bond donors
0
H-bond acceptors
6
Formal charge
0

via PubChem

Research

6 papers

via PubMed

~8 min read

Encyclopedic overview

8 sections
Contents
  • Medical uses
  • Pharmacology
  • Pharmacokinetics
  • Pharmacodynamics
  • Efferocytosis
  • Toxicology
  • Chemistry
  • References

Tiotixene, or thiothixene, is a typical antipsychotic sold under the brand name Navane which is predominantly utilised to treat 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.

Excerpted from Wikipedia’s “(Z)-thiothixene” article, available under the CC BY-SA 4.0 licence.