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Chemical Compound Review

hexestrol     4-[4-(4-hydroxyphenyl)hexan- 3-yl]phenol

Synonyms: Estrifar, Estronal, Exestrol, Synthovo, Esestrolo, ...
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Disease relevance of hexestrol


High impact information on hexestrol


Biological context of hexestrol


Anatomical context of hexestrol

  • On the first and second days after Hexoestrol administration there is an increase in the number of ribosomes and polyribosomes lying free in the cytoplasm of the endothelial cells [13].
  • Diethylstilbestrol (DES) and four derivatives, viz. tetrafluoro-DES, 3'-hydroxy-DES, Z,Z-dienestrol and hexestrol, were examined for their abilities to form superoxide radicals and to induce DNA strand breaks in the presence of horseradish peroxidase/hydrogen peroxide metabolism in a cell-free system [14].
  • High doses of hexoestrol produced a loss of contractility of the papillary muscle without significant alterations of the amplitude and shape of the electrical activity recorded extracellularly [15].
  • These results indicate that hexoestrol probably acts by blocking certain steps in the process by which extracellular and/or superficially bound Ca ions move to the contractile machinery in cardiac and in smooth muscle cells [15].
  • The synthetic oestrogen hexoestrol, administered at 60 mg/kg/day for 4 days to female rats in 3 studies, caused the following mean changes in the relative weights of some of the principal organs: liver (+37%), spleen (-11%), adrenals (+43%), kidneys (+3%), pituitary (+23%), uterus (+49%), and ovaries (+13%) [1].

Associations of hexestrol with other chemical compounds

  • Estrogen photoaffinity labels. 2. Reversible binding and covalent attachment of photosensitive hexestrol derivatives to the uterine estrogen receptor [16].
  • Photolysis of 3,5-diiodohexestrol in methanol results in rapid deiodination to 3-iodohexestrol; further reduction to hexestrol is slower [17].
  • Ketononestrol aziridine [(6R,TS)1-(N-aziridinyl)6,7-bis-(4-hydroxyphenyl)5-nonamone (KNA)], an aziridine derivative of hexestrol, is an estrogenic affinity label for the estrogen receptor (ER) [18].
  • On the other hand, meso-hexestrol was distinguished from others by inhibition of microtubule assembly and formation of a large amount of aggregates from purified tubulin in the presence of MgCl2 and DMSO [19].
  • Our preliminary findings showed that geiparvarin and some derivatives obtained from its conjugation with diethylstilboestrol and meso-hexestrol significantly inhibit taxol-induced in vitro polymerization of both tubulin and microtubular protein [20].

Gene context of hexestrol


Analytical, diagnostic and therapeutic context of hexestrol


  1. Pituitary-related weight changes affecting the liver, uterus and adrenal glands of rats treated with hexoestrol and clomiphene in high doses. Hart, J.E. Toxicology (1990) [Pubmed]
  2. Subacute toxicity of diethylstilboestrol and hexoestrol in the female rat, and the effects of clomiphene pretreatment. Hart, J.E. Food Chem. Toxicol. (1988) [Pubmed]
  3. Hexestrol residues and metabolites in the tissues of wethers injected with hexestrol dicaprylate or hexestrol. Tobioka, H., Kawashima, R. J. Anim. Sci. (1985) [Pubmed]
  4. Effect of sex hormones on the response of mice to infection with Toxoplasma gondii. Kittas, C., Henry, L. British journal of experimental pathology. (1980) [Pubmed]
  5. Interaction of some estrogenic drugs with tubulin. Formation of twisted ribbon structures. Chaudoreille, M.M., Peyrot, V., Braguer, D., Crevat, A. Mol. Pharmacol. (1987) [Pubmed]
  6. Conformational analysis of nonsteroidal estrogens: The effect of conformer populations on the binding affinity of meso- and dl-hexestrol to the estrogen receptor. Kilbourn, M.R., Arduengo, A.J., Park, J.T., Katzenellenbogen, J.A. Mol. Pharmacol. (1981) [Pubmed]
  7. Ultrastructural effects of sex hormones and infection on lymph node post-capillary venules. Kittas, C., Henry, L. J. Pathol. (1980) [Pubmed]
  8. Effect of gonadectomy and oestrogen administration on the response of lymph-node post-capillary venules to infection with Toxoplasma gondii. Kittas, C., Henry, L. J. Pathol. (1979) [Pubmed]
  9. Metabolic activation and formation of DNA adducts of hexestrol, a synthetic nonsteroidal carcinogenic estrogen. Jan, S.T., Devanesan, P.D., Stack, D.E., Ramanathan, R., Byun, J., Gross, M.L., Rogan, E.G., Cavalieri, E.L. Chem. Res. Toxicol. (1998) [Pubmed]
  10. Carcinogenic antioxidants. Diethylstilboestrol, hexoestrol and 17 alpha-ethynyloestradiol. Wiseman, H., Halliwell, B. FEBS Lett. (1993) [Pubmed]
  11. The antioxidant action of synthetic oestrogens involves decreased membrane fluidity: relevance to their potential use as anticancer and cardioprotective agents compared to tamoxifen? Wiseman, H., Quinn, P. Free Radic. Res. (1994) [Pubmed]
  12. Mitotic inhibition and aneuploidy induction by naturally occurring and synthetic estrogens in Chinese hamster cells in vitro. Wheeler, W.J., Cherry, L.M., Downs, T., Hsu, T.C. Mutat. Res. (1986) [Pubmed]
  13. An electron microscopic study of the changes induced by oestrogens on the lymph-node post-capillary venules. Kittas, C., Henry, L. J. Pathol. (1979) [Pubmed]
  14. Possible role of oxygen radicals in cell transformation by diethylstilbestrol and related compounds. Epe, B., Schiffmann, D., Metzler, M. Carcinogenesis (1986) [Pubmed]
  15. Effects of hexoestrol on the contractility of the isolated, blood-perfused canine papillary muscle and of the guinea-pig ileum. Himori, N. Naunyn Schmiedebergs Arch. Pharmacol. (1977) [Pubmed]
  16. Estrogen photoaffinity labels. 2. Reversible binding and covalent attachment of photosensitive hexestrol derivatives to the uterine estrogen receptor. Katzenellenbogen, J.A., Carlson, K.E., Johnson, H.J., Myers, H.N. Biochemistry (1977) [Pubmed]
  17. Iodohexestrols. I. Synthesis and photoreactivity of iodinated hexestrol derivatives. Katzenellenbogen, J.A., Hsiung, H.M. Biochemistry (1975) [Pubmed]
  18. Ketononestrol aziridine, an agonistic estrogen receptor affinity label: study of its bioactivity and estrogen receptor covalent labeling. Elliston, J.F., Zablocki, J.A., Katzenellenbogen, B.S., Katzenellenbogen, J.A. Endocrinology (1987) [Pubmed]
  19. Effects of synthetic estrogens, (R,R)-(+)-, (S,S)-(-)-, dl- and meso-hexestrol stereoisomers on microtubule assembly. Sakakibara, Y., Hasegawa, K., Oda, T., Saitô, H., Kodama, M., Hirata, A., Matsuhashi, M., Sato, Y. Biochem. Pharmacol. (1990) [Pubmed]
  20. Geiparvarin and derivatives in combination with taxol: effect on microtubular organization in 3T3 fibroblasts. Miglietta, A., Bocca, C., Rampa, A., Bisi, A., Gabriel, L. Anticancer Drug Des. (1997) [Pubmed]
  21. Ring-substituted 1,2-dialkylated 1,2-bis(hydroxyphenyl)ethanes. 1. Synthesis and estrogen receptor binding affinity of 2,2'- and 3,3'-disubstituted hexestrols. Hartmann, R.W., Schwarz, W., Schönenberger, H. J. Med. Chem. (1983) [Pubmed]
  22. Degradation of bisphenol A by the lignin-degrading enzyme, manganese peroxidase, produced by the white-rot basidiomycete, Pleurotus ostreatus. Hirano, T., Honda, Y., Watanabe, T., Kuwahara, M. Biosci. Biotechnol. Biochem. (2000) [Pubmed]
  23. Carbon-14-labeled diethylstilbestrol synthesis by the McMurry method: concurrent formation of hexestrol. Feil, V., Aschbacher, P.W., Lamoureaux, C.H., Mansager, E.R. Science (1977) [Pubmed]
  24. Distribution of hexoestrol residues in caponised chickens. Herriman, I.D., Harwood, D.J., Blandford, T., Lindsay, D. Vet. Rec. (1982) [Pubmed]
  25. Determination of hexoestrol residues in animal tissues based on enzyme-linked immunosorbent assay and comparison with liquid chromatography-tandem mass spectrometry. Xu, C., Peng, C., Liu, L., Wang, L., Jin, Z., Chu, X. Journal of pharmaceutical and biomedical analysis. (2006) [Pubmed]
  26. Identification of several stilbene derivatives in bovine urine by means of high performance liquid chromatographic fractionation and immunochemical detection. Jansen, E.H., van den Berg, R.H., van Blitterswijk, H., Both-Miedema, R., Stephany, R.W. The Veterinary quarterly. (1984) [Pubmed]
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