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Chemical Compound Review

EQUILINE     3-hydroxy-13-methyl- 9,11,12,14,15,16...

Synonyms: CCRIS 9074, AG-J-94889, BSPBio_001972, KBioGR_002069, KBioSS_000765, ...
 
 
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Disease relevance of equilin

 

High impact information on equilin

 

Biological context of equilin

 

Anatomical context of equilin

  • A fetal gonad--placental system is proposed for equilin production, 3 beta-hydroxy-5,7-pregnadien-20-one being a precursor for 3 beta-hydroxy-5,7-androstadien-17-one in the fetal gonad and the latter being the precursor of equilin in the placenta [10].
  • Equilin induced highly significant increases in the growth of both the macro and micro features of cortical nerve cell morphology [11].
  • Analysis of the regional selectivity of equilin-induced neurotrophism in the cerebral cortex demonstrated that equilin significantly increased the growth of neurons from the frontal, temporal, and occipital regions, with neurons from the parietal region also influenced, though more modestly [11].
  • In the human endometrium, equilin is metabolized to 2-hydroxy and 4-hydroxy equilin, with 2-hydroxylation being predominant [12].
  • Unlike endogenous catechol estrogens, both equilin and equilenin were primarily converted by rat liver microsomes to 4-hydroxylated rather than 2-hydroxylated o-quinone GSH conjugates [1].
 

Associations of equilin with other chemical compounds

  • In this communication we have shown that equine estrogens (especially equilin) exhibit higher antioxidant potency (as measured by fatty acids and sterols oxidation) when compared to estrone and estradiol-17 beta [13].
  • In contrast with Eq and E1, only the low affinity binding sites were found (apparent Ka congruent to 1 X 10(4) M-1) [14].
  • The two-state excited-state proton-transfer process for d-equilenin [d-3-hydroxyestra-1,3,-5(10),6,8-pentaen-17-one] and dihydroequilenin is found to depend both on pH and on proton acceptor concentration [15].
 

Gene context of equilin

  • Mixtures of estradiol and six equine estrogens, including equilin, equilenin, 8,9-dehydroestrone, and their 17beta-hydroxyl derivatives, were assayed simultaneously to determine their relative binding to human ER-alpha and ER-beta [16].
  • The half-life of equilin was approximately 19-27 min, and the MCR of equilin was calculated to be 1982 liters/day/m2 in the normal man and 3300 liters/day/m2 in the normal postmenopausal woman [7].
  • EST/ISH cells were approximately 3-10-fold less sensitive to the equine estrogens equilin and 17-equilin as compared to control cells [17].
  • When human urine extract was separated by a two-dimensional thin-layer chromatography, several spot fractions inhibited P-gp function, and equilin was identified in one fraction as an endogenous P-gp inhibitor [18].
 

Analytical, diagnostic and therapeutic context of equilin

References

  1. The major metabolite of equilin, 4-hydroxyequilin, autoxidizes to an o-quinone which isomerizes to the potent cytotoxin 4-hydroxyequilenin-o-quinone. Zhang, F., Chen, Y., Pisha, E., Shen, L., Xiong, Y., van Breemen, R.B., Bolton, J.L. Chem. Res. Toxicol. (1999) [Pubmed]
  2. Structure of the ternary complex of human 17beta-hydroxysteroid dehydrogenase type 1 with 3-hydroxyestra-1,3,5,7-tetraen-17-one (equilin) and NADP+. Sawicki, M.W., Erman, M., Puranen, T., Vihko, P., Ghosh, D. Proc. Natl. Acad. Sci. U.S.A. (1999) [Pubmed]
  3. Interactions of putative estrogens with the intracellular receptor complex in mouse Leydig cells: relationship to preneoplastic hyperplasia. Juriansz, R.L., Huseby, R.A., Wilcox, R.B. Cancer Res. (1988) [Pubmed]
  4. Coordinate regulation of the production and signaling of retinoic acid by estrogen in the human endometrium. Deng, L., Shipley, G.L., Loose-Mitchell, D.S., Stancel, G.M., Broaddus, R., Pickar, J.H., Davies, P.J. J. Clin. Endocrinol. Metab. (2003) [Pubmed]
  5. Pharmacokinetics of 17 beta-dihydroequilin sulfate and 17 beta-dihydroequilin in normal postmenopausal women. Bhavnani, B.R., Cecutti, A. J. Clin. Endocrinol. Metab. (1994) [Pubmed]
  6. Metabolic clearance rate of equilin sulfate and its conversion to plasma equilin, conjugated and unconjugated equilenin, 17 beta-dihydroequilin, and 17 beta-dihydroequilenin in normal postmenopausal women and men under steady state conditions. Bhavnani, B.R., Cecutti, A. J. Clin. Endocrinol. Metab. (1993) [Pubmed]
  7. Pharmacokinetics of equilin and equilin sulfate in normal postmenopausal women and men. Bhavnani, B.R., Woolever, C.A., Benoit, H., Wong, T. J. Clin. Endocrinol. Metab. (1983) [Pubmed]
  8. The use of equilin as an internal standard to quantitate estriol in pregnancy urine. Gold, M., Mathew, G. Clin. Biochem. (1977) [Pubmed]
  9. Patterns of urinary oestrogen excretion in individual pregnant mares. Raeside, J.I., Liptrap, R.M. J. Reprod. Fertil. Suppl. (1975) [Pubmed]
  10. Biosynthesis of 3 beta-hydroxy-5,7-pregnadien-20-one by the horse fetal gonad. Tait, A.D., Hodge, L.C., Allen, W.R. FEBS Lett. (1983) [Pubmed]
  11. Equilin, a principal component of the estrogen replacement therapy premarin, increases the growth of cortical neurons via an NMDA receptor-dependent mechanism. Brinton, R.D., Proffitt, P., Tran, J., Luu, R. Exp. Neurol. (1997) [Pubmed]
  12. Pharmacokinetics and pharmacodynamics of conjugated equine estrogens: chemistry and metabolism. Bhavnani, B.R. Proc. Soc. Exp. Biol. Med. (1998) [Pubmed]
  13. Antioxidant potential of specific estrogens on lipid peroxidation. Subbiah, M.T., Kessel, B., Agrawal, M., Rajan, R., Abplanalp, W., Rymaszewski, Z. J. Clin. Endocrinol. Metab. (1993) [Pubmed]
  14. Transport of equine estrogens: binding of conjugated and unconjugated equine estrogens with human serum proteins. Pan, C.C., Woolever, C.A., Bhavnani, B.R. J. Clin. Endocrinol. Metab. (1985) [Pubmed]
  15. Excited-state proton transfer of equilenin and dihydroequilenin: interaction with bilayer vesicles. Davenport, L., Knutson, J.R., Brand, L. Biochemistry (1986) [Pubmed]
  16. Ultrafiltration tandem mass spectrometry of estrogens for characterization of structure and affinity for human estrogen receptors. Sun, Y., Gu, C., Liu, X., Liang, W., Yao, P., Bolton, J.L., van Breemen, R.B. J. Am. Soc. Mass Spectrom. (2005) [Pubmed]
  17. Regulation of estrogen activity by sulfation in human Ishikawa endometrial adenocarcinoma cells. Kotov, A., Falany, J.L., Wang, J., Falany, C.N. J. Steroid Biochem. Mol. Biol. (1999) [Pubmed]
  18. Interaction of endogenous compounds in human and rat urine with P-glycoprotein. Murakami, T., Fukuda, T., Yumoto, R., Nagai, J., Kuramoto, T., Takano, M. Drug Metab. Pharmacokinet. (2002) [Pubmed]
  19. A radioimmunoassay for equilin in equine pregnancy plasma. Park, B.K., Rance, T.A., Dean, P.D. FEBS Lett. (1976) [Pubmed]
  20. Effect of temperature on separation of estradiol stereoisomers and equilin by liquid chromatography using mobile phases modified with beta-cyclodextrin. Lamparczyk, H., Zarzycki, P.K. Journal of pharmaceutical and biomedical analysis. (1995) [Pubmed]
  21. HPLC-fluorescence determination of equilin and equilenin in postmenopausal women's urine. Gatti, R., Franchina, M., Gioia, M.G., Cavrini, V. Biomed. Chromatogr. (2000) [Pubmed]
  22. A radioimmunoassay for equilin in post-menopausal plasma: plasma levels of equilin determined after oral administration of conjugated equine oestrogens (premarin). Morgan, M.R., Whittaker, P.G., Fuller, B.P., Dean, P.D. J. Steroid Biochem. (1980) [Pubmed]
 
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