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Chemical Compound Review

Nafoxidine     1-[2-[4-(6-methoxy-2-phenyl- 3,4...

Synonyms: Nafoxidina, Nafoxidinum, CHEMBL28211, SureCN153125, CHEBI:134557, ...
 
 
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Disease relevance of Nafoxidine

 

High impact information on Nafoxidine

 

Chemical compound and disease context of Nafoxidine

 

Biological context of Nafoxidine

 

Anatomical context of Nafoxidine

  • Incubation of the cells for 4 to 6 days with the antiestrogen nafoxidine, however, resulted in a dose-dependent reduction in cytosol DNA polymerase activity to one-half that observed in untreated cells [20].
  • Concurrent incubation of the HeLa cells and estrogens with the antiestrogen nafoxidine blocked the subsequent increase in adherence [21].
  • Acute administration of 17 beta-estradiol or the antiestrogen nafoxidine to immature rats produces quantitatively similar responses in the uterine stroma and myometrium, although the responses to nafoxidine occur at slightly later times [22].
  • Triphenylethylenes [Tamoxifen (TAM), TAM metabolites, and nafoxidine] were found to inhibit Ca2+-calmodulin (CaM)-dependent cAMP phosphodiesterase (PDE) activity of the quail oviduct, whereas 17 beta-estradiol was inactive [23].
  • By itself, the triarylethylene antiestrogen, nafoxidine, slightly increased hepatocyte 30MDG uptake, while in combination with estrogen, nafoxidine completely blocked the effects of both E2 and 17 alpha-ethynyl estradiol [24].
 

Associations of Nafoxidine with other chemical compounds

  • Female steroid hormones and lipoprotein synthesis in the cockerel: effects of progesterone and nafoxidine on the estrogenic stimulation of very low density lipoproteins (VLDL) synthesis [25].
  • E2 treatment led to a substantial induction of cytoplasmic progestin receptors (approximately 2-fold in the HPOA, approximately 4-fold in the pituitary, and approximately 7-fold in the uterus after 48 h), and this process was considerably inhibited by nafoxidine [26].
  • Inhibition of volume-regulated anion channels in cultured endothelial cells by the anti-oestrogens clomiphene and nafoxidine [27].
  • It is postulated that CI-628 directly affects the uterus to reduce production of oestrogen receptor protein, while nafoxidine affects the development of the uterine phosphogluconate oxidative pathway indirectly through impaired ovarian function [28].
  • Vaginal ADL and uterine myometrial involution were also encountered in 35-day-old mice given neonatal injections of 2-200 micrograms Tx, 200 micrograms clomiphene (Clm) and 200 micrograms nafoxidine (Naf), respectively [29].
 

Gene context of Nafoxidine

 

Analytical, diagnostic and therapeutic context of Nafoxidine

  • After treatment with 5 micrograms nafoxidine for 24 h, uterine cytosol contains approximately one half the total number of estrogen receptors originally present in uteri of untreated animals, and uterine nuclei also contain approximately one half the receptors originally present in unstimulated tissue [34].
  • 1. We have used the whole-cell patch clamp technique to study the effect of the partial anti-oestrogens clomiphene and nafoxidine, the pure anti-oestrogens ICI 182,780 and RU 58,668 and the oestrogen ss-estradiol, on the volume-regulated anion channel (VRAC) in cultured pulmonary artery endothelial (CPAE) cells [27].
  • In a selected group of patients with metastatic breast cancer who had, in the past, undergone adrenalectomy, Nafoxidine therapy produced objective tumor regression in six out of ten patients [35].

References

  1. Estrogens and antiestrogens stimulate release of bone resorbing activity by cultured human breast cancer cells. Valentin-Opran, A., Eilon, G., Saez, S., Mundy, G.R. J. Clin. Invest. (1985) [Pubmed]
  2. Effects of 4-nitroestrone 3-methyl ether on dimethylbenz(a)anthracene-induced mammary tumors. Rozhin, J., Ludwig, E.H., Corombos, J., Odden, D., Horwitz, J.P., Hughes, R., Hughes, D.E., Wilson, E., Brooks, S.C. Cancer Res. (1983) [Pubmed]
  3. Effect of the anti-estrogen, Nafoxidine, on NZB/W autoimmune disease. Duvic, M., Steinberg, A.D., Klassen, L.W. Arthritis Rheum. (1978) [Pubmed]
  4. Gap junction modulation in rat uterus. II. Effects of antiestrogens on myometrial and serosal cells. Burghardt, R.C., Mitchell, P.A., Kurten, R. Biol. Reprod. (1984) [Pubmed]
  5. Dissociation of uterine eosinophilia and water imbibition from other estrogen-induced responses by nafoxidine pretreatment. Galand, P., Tchernitchin, N., Tchernitchin, A.N. Mol. Cell. Endocrinol. (1985) [Pubmed]
  6. Estrogenic properties of 3,9-dihydroxy-7,12-dimethylbenz[a]anthracene in rats. Morreal, C.E., Schneider, S.L., Sinha, D.K., Bronstein, R.E. J. Natl. Cancer Inst. (1979) [Pubmed]
  7. Tumor formation in preneoplastic mammary nodule lines in mice treated with nafoxidine, testosterone, and 2-bromo-alpha-ergocryptine. Medina, D. J. Natl. Cancer Inst. (1977) [Pubmed]
  8. Role of estrogen receptor binding and transcriptional activity in the stimulation of hyperestrogenism and nuclear bodies. Clark, J.H., Hardin, J.W., Padykula, H.A., Cardasis, C.A. Proc. Natl. Acad. Sci. U.S.A. (1978) [Pubmed]
  9. Specific binding and biological response of antiestrogens in the fetal uterus of the guinea pig. Gulino, A., Pasqualini, J.R. Cancer Res. (1980) [Pubmed]
  10. Permanent chondrification in the pelvis and occurrence of hernias in mice treated neonatally with tamoxifen. Iguchi, T., Irisawa, S., Uchima, F.D., Takasugi, N. Reprod. Toxicol. (1988) [Pubmed]
  11. Influence of anti-oestrogens on gonadotrophin secretion in control and ACTH-infused immature rats. Mann, D.R., Blank, M.S., Sridaran, R., Castracane, V.D., Eldridge, C., Collins, D.C. Acta Endocrinol. (1984) [Pubmed]
  12. Controlled clinical trial of L-dopa and nafoxidine in advanced breast cancer: an E.O.R.T.C. study. Engelsman, E., Heuson, J.C., Blonk Van Der Wijst, J., Drochmans, A., Maass, H., Cheix, F., Sobrinho, L.G., Nowakowski, H. British medical journal. (1975) [Pubmed]
  13. Treatment of renal carcinoma: a phase III randomized trial of oral medroxyprogesterone (Provera), hydroxyurea, and nafoxidine. Stolbach, L.L., Begg, C.B., Hall, T., Horton, J. Cancer treatment reports. (1981) [Pubmed]
  14. Effects of anti-estrogens on early pregnancy in guinea pigs. Wisel, M.S., Datta, J.K., Saxena, R.N. International journal of fertility and menopausal studies. (1994) [Pubmed]
  15. Crystal and molecular structure of nafoxidine and stereochemical features of anticancer antiestrogens. Camerman, N., Chan, L.Y., Camerman, A. J. Med. Chem. (1980) [Pubmed]
  16. A high-affinity estrogen-binding protein in rat placental trophoblast. McCormack, S.A., Glasser, S.R. Endocrinology (1976) [Pubmed]
  17. Estrogen control of progesterone receptor in human breast cancer: role of estradiol and antiestrogen. Horwitz, K.B., Koseki, Y., McGuire, W.L. Endocrinology (1978) [Pubmed]
  18. Antagonism of estrogen receptor and calmodulin association by antiestrogens is not dependent on an interaction with calmodulin. Rowlands, M.G., Grimshaw, R., Jarman, M., Bouhoute, A., Leclercq, G. Biochem. Pharmacol. (1997) [Pubmed]
  19. The antioxidant action of a pure antioestrogen: ability to inhibit lipid peroxidation compared to tamoxifen and 17 beta-oestradiol and relevance to its anticancer potential. Wiseman, H. Biochem. Pharmacol. (1994) [Pubmed]
  20. Effects of estrogen and antiestrogen on DNA polymerase in human breast cancer. Edwards, D.P., Murthy, S.R., McGuire, W.L. Cancer Res. (1980) [Pubmed]
  21. Effect of estrogens on bacterial adherence to HeLa cells. Sugarman, B., Epps, L.R. Infect. Immun. (1982) [Pubmed]
  22. Stimulatory and inhibitory effects of estrogen and antiestrogen on uterine cell division. Mukku, V.R., Kirkland, J.L., Hardy, M., Stancel, G.M. Endocrinology (1981) [Pubmed]
  23. Effects of tamoxifen, tamoxifen metabolites, and nafoxidine on adenosine 3',5'-monophosphate phosphodiesterase: correlations with growth inhibitory activities but not estrogen receptor affinities. Fanidi, A., Courion-Guichardaz, C., Fayard, J.M., Pageaux, J.F., Laugier, C. Endocrinology (1989) [Pubmed]
  24. Estrogen stimulation of 3-o-methyl-D-glucose uptake in isolated rat hepatocytes. Madar, Z., MacLusky, N.J., Naftolin, F. Endocrinology (1982) [Pubmed]
  25. Female steroid hormones and lipoprotein synthesis in the cockerel: effects of progesterone and nafoxidine on the estrogenic stimulation of very low density lipoproteins (VLDL) synthesis. Chan, L., Jackson, R.L., Means, A.R. Endocrinology (1977) [Pubmed]
  26. Effects of nafoxidine on the luteinizing hormone surge: temporal distribution of estrogen receptors and induction of cytoplasmic progestin receptors in the hypothalamus-preoptic area, pituitary, and uterus of the immature rat. Attardi, B., Palumbo, L.A. Endocrinology (1981) [Pubmed]
  27. Inhibition of volume-regulated anion channels in cultured endothelial cells by the anti-oestrogens clomiphene and nafoxidine. Maertens, C., Droogmans, G., Chakraborty, P., Nilius, B. Br. J. Pharmacol. (2001) [Pubmed]
  28. Effect of neonatal exposure to the antioestrogens nafoxidine and CI-628 upon the development of the uterus in the prepubertal rat. Campbell, P.S., Satterfield, P.M. J. Reprod. Fertil. (1988) [Pubmed]
  29. Changes in the uterus and vagina of mice treated neonatally with antiestrogens. Iguchi, T., Todoroki, R., Yamaguchi, S., Takasugi, N. Acta anatomica. (1989) [Pubmed]
  30. Antiestrogens inhibit endothelial cell growth stimulated by angiogenic growth factors. Gagliardi, A.R., Hennig, B., Collins, D.C. Anticancer Res. (1996) [Pubmed]
  31. Nafoxidine modulates the expression of matrix-metalloproteinase-2 (MMP-2) and tissue inhibitor of metalloproteinases-1 (TIMP-1) in endothelial cells. De Lorenzo, M.S., Alonso, D.F., Gomez, D.E. Anticancer Res. (2000) [Pubmed]
  32. Ligand-dependent and -independent function of the transactivation regions of the human estrogen receptor in yeast. Pham, T.A., Hwung, Y.P., Santiso-Mere, D., McDonnell, D.P., O'Malley, B.W. Mol. Endocrinol. (1992) [Pubmed]
  33. Modulation of the estradiol-induced luteinizing hormone surge by progesterone or antiestrogens: effects on pituitary gonadotropin-releasing hormone receptors. Attardi, B., Happe, H.K. Endocrinology (1986) [Pubmed]
  34. Selective blockade of estrogen-induced uterine responses by the antiestrogen nafoxidine. Gardner, R.M., Kirkland, J.L., Stancel, G.M. Endocrinology (1978) [Pubmed]
  35. Clinical trial of nafoxidine in adrenalectomized patients with advanced breast cancer. Jain, J., Samal, B., Singhakowinta, A., Vaitkevicius, V.K. Cancer (1977) [Pubmed]
 
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