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Chemical Compound Review

Thioxanthene     9H-thioxanthene

Synonyms: Thioxanthine, SureCN8717, CHEMBL79451, AG-E-81378, CHEBI:51055, ...
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Disease relevance of Thioxanthene


High impact information on Thioxanthene

  • Thioxanthine is toxic for mammalian cells transformed by the dominant selectable marker gpt [5].
  • In this study, we demonstrate that inhibition of Pgp-mediated drug transport by cis-(Z)-flupentixol, a thioxanthene derivative, occurs through an allosteric mechanism [6].
  • Among 1,152 psychiatric inpatients who received a phenothiazine, a butyrophenone, or a thioxanthene, 116 developed dystonia attributed to one or more of these drugs [7].
  • The X-ray structure of the charge-transfer complex (CTC) of 10 with 2,4,5,7-tetranitrofluorene-9-dicyanomethylenefluorene (DTeF) [stoichiometry: 10(.+)(DTeF)(2) (.-)2 PhCl] reveals a twisted conformation of 10(.+) (driven by the bulky thioxanthene moiety) and provides a very rare example of segregated stacking of a fluorene acceptor in a CTC [8].
  • In summary, we demonstrate that allosteric modulation by cis-(Z)-flupentixol is mediated through its interaction with Pgp at a site specific for tricyclic ring-containing Pgp modulators of thioxanthene and phenothiazine backbone, independent of other cellular components and the phosphorylation status of the protein [9].

Biological context of Thioxanthene


Anatomical context of Thioxanthene


Associations of Thioxanthene with other chemical compounds


Gene context of Thioxanthene

  • Thioxanthine, which is known to be a strong inhibitor of TPMT when added to the assay system to give a 2% contamination, reduced TPMT activity from 100% to 72% [18].
  • The compounds, possessing thioxanthene and dihydroanthracene moieties as the terminal substituents, show a fast rotation around the butatriene bonds at ambient temperatures (DeltaG() = 13.7 and 14.9 kcal/mol, respectively) [19].
  • When the thioxanthene neuroleptics 3H-cis (Z)-flupenthixol or 3H-piflutixol are used as ligands D-1 receptors coupled to adenylate cyclase can be detected [20].

Analytical, diagnostic and therapeutic context of Thioxanthene

  • Separation of (Z)- and (E)-isomers of thioxanthene and dibenz[b,e]oxepin derivatives with calixarenes and resorcinarenes as additives in nonaqueous capillary electrophoresis [21].
  • Separation of cis- and trans-isomers of thioxanthene and dibenz[b,e]oxepin derivatives on calixarene- and resorcinarene-bonded high-performance liquid chromatography stationary phases [22].
  • The thioxanthene neuroleptic flupenthixol, which can be given intramuscularly (i.m.) for improving compliance, has been studied as a possible anti-craving drug both in animal models of alcoholism and some clinical studies [23].


  1. The toxicity of thioxanthene neuroleptics to isolated rat liver cells. Abernathy, C.O., Zimmerman, H.J. Proc. Soc. Exp. Biol. Med. (1975) [Pubmed]
  2. Reversal of multidrug resistance in murine fibrosarcoma cells by thioxanthene flupentixol. Fan, D., Poste, G., Seid, C., Earnest, L.E., Bull, T., Clyne, R.K., Fidler, I.J. Investigational new drugs. (1994) [Pubmed]
  3. Hyponatremia in patients with schizophrenia. Gleadhill, I.C., Smith, T.A., Yium, J.J. South. Med. J. (1982) [Pubmed]
  4. Gastric responses to flupenthixol, a new thioxanthene derivative in rats. Vyas, D.S., Godhwani, J.L., Sharma, V.N. Indian J. Physiol. Pharmacol. (1977) [Pubmed]
  5. Selection against expression of the Escherichia coli gene gpt in hprt+ mouse teratocarcinoma and hybrid cells. Besnard, C., Monthioux, E., Jami, J. Mol. Cell. Biol. (1987) [Pubmed]
  6. Allosteric modulation of human P-glycoprotein. Inhibition of transport by preventing substrate translocation and dissociation. Maki, N., Hafkemeyer, P., Dey, S. J. Biol. Chem. (2003) [Pubmed]
  7. Drug-induced dystonia. Swett, C. The American journal of psychiatry. (1975) [Pubmed]
  8. Remarkable interplay of redox states and conformational changes in a sterically crowded, cross-conjugated tetrathiafulvalene vinylog. Amriou, S., Perepichka, I.F., Batsanov, A.S., Bryce, M.R., Rovira, C., Vidal-Gancedo, J. Chemistry (Weinheim an der Bergstrasse, Germany) (2006) [Pubmed]
  9. Biochemical and pharmacological properties of an allosteric modulator site of the human P-glycoprotein (ABCB1). Maki, N., Dey, S. Biochem. Pharmacol. (2006) [Pubmed]
  10. Pharmacokinetic interaction between carbamazepine and neuroleptics after combined prolonged treatment in rats. Daniel, W., Janczar, L., Danek, L., Legrum, W., Netter, K.J. Naunyn Schmiedebergs Arch. Pharmacol. (1992) [Pubmed]
  11. In vitro modulation of human neutrophil chemotaxis by cis(Z)- and trans(E)-clopenthixol, and chlorpromazine. Rechnitzer, C., Kristiansen, J.E., Kharazmi, A. Acta pathologica, microbiologica, et immunologica Scandinavica. Section C, Immunology. (1985) [Pubmed]
  12. Schizophrenic patients treated with high dose phenothiazine or thioxanthene become deficient in polyunsaturated fatty acids in their thrombocytes. Fischer, S., Kissling, W., Kuss, H.J. Biochem. Pharmacol. (1992) [Pubmed]
  13. Effects of chlorprothixene isomers on platelet 5-hydroxytryptamine receptors: evidence for different 5-hydroxytryptamine conformations at uptake and stimulatory sites. Drummond, A.H., Whigham, K.A., Prentice, C.R. Eur. J. Pharmacol. (1976) [Pubmed]
  14. Antimicrobial potentiality of the thioxanthene flupenthixol through extensive in vitro and in vivo experiments. Jeyaseeli, L., Gupta, A.D., Asok Kumar, K., Mazumdar, K., Dutta, N.K., Dastidar, S.G. Int. J. Antimicrob. Agents (2006) [Pubmed]
  15. Zuclopenthixol treatment of behavioral disturbances in mentally retarded children and adolescents: an open-label study. Spivak, B., Mozes, T., Mester, R., Kodelik, M., Weizman, A. Journal of child and adolescent psychopharmacology. (2001) [Pubmed]
  16. An ethopharmacological assessment of the effects of zuclopenthixol on agonistic interactions in male mice. Manzaneque, J.M., Navarro, J.F. Methods and findings in experimental and clinical pharmacology. (1999) [Pubmed]
  17. Quantification of the antipsychotics flupentixol and haloperidol in human serum by high-performance liquid chromatography with ultraviolet detection. Walter, S., Bauer, S., Roots, I., Brockmöller, J. J. Chromatogr. B Biomed. Sci. Appl. (1998) [Pubmed]
  18. Inhibition of thiopurine S-methyltransferase activity by impurities in commercially available substrates: a factor for differing results of TPMT measurements. Kröplin, T., Fischer, C., Iven, H. Eur. J. Clin. Pharmacol. (1999) [Pubmed]
  19. Twin-rotor system created on a [4]radialene frame. Kuwatani, Y., Yamamoto, G., Iyoda, M. Org. Lett. (2003) [Pubmed]
  20. Biochemical and pharmacological differentiation of neuroleptic effect on dopamine D-1 and D-2 receptors. Hyttel, J., Christensen, A.V. J. Neural Transm. Suppl. (1983) [Pubmed]
  21. Separation of (Z)- and (E)-isomers of thioxanthene and dibenz[b,e]oxepin derivatives with calixarenes and resorcinarenes as additives in nonaqueous capillary electrophoresis. Sokoliess, T., Gronau, M., Menyes, U., Roth, U., Jira, T. Electrophoresis (2003) [Pubmed]
  22. Separation of cis- and trans-isomers of thioxanthene and dibenz[b,e]oxepin derivatives on calixarene- and resorcinarene-bonded high-performance liquid chromatography stationary phases. Sokoliess, T., Menyes, U., Roth, U., Jira, T. Journal of chromatography. A. (2002) [Pubmed]
  23. Flupenthixol in relapse prevention in schizophrenics with comorbid alcoholism: results from an open clinical study. Soyka, M., Aichmüller, C., v Bardeleben, U., Beneke, M., Glaser, T., Hornung-Knobel, S., Wegner, U. European addiction research. (2003) [Pubmed]
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