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Chemical Compound Review

Ovestin     (8R,9S,13S,14S,16R,17S)-13- methyl-6,7,8,9...

Synonyms: Colpogyn, Destriol, Estriolo, Gynaesan, Hormomed, ...
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Disease relevance of estriol

  • To evaluate the relationship between these two breast-cancer risk indicators the urine oestriol ratio was determined for recently delivered uniparous women aged 19-23, 25-27, and 29-34 years and nulliparous women of comparable ages [1].
  • FINDINGS: After multivariate adjustment, oral use of oestriol 1-2 mg daily increased the relative risk of endometrial cancer and endometrial atypical hyperplasia: the odds ratios for at least 5 years of use compared with never use were 3.0 (95% CI 2.0-4.4) and 8.3 (4.0-17.4), respectively [2].
  • Deficiency of steroid sulphatase (STS) is associated with ichthyosis, with failure of the placental production of oestriol in late pregnancy and with difficulties in childbirth [3].
  • Growth-promoting effect of oestriol in a lymphoma lacking oestrogen receptors [4].
  • Maternal serum unconjugated oestriol as an antenatal screening test for Down's syndrome [5].

Psychiatry related information on estriol


High impact information on estriol

  • Second trimester maternal serum human chorionic gonadotropin and unconjugated oestriol levels in blacks and whites [8].
  • In the total series of 794 patients, hypoglycaemia had a significant association with low oestriol excretion (p less than 0.01), fetal growth retardation (p less than 0-05), low Apgar score (p less than 0.05), and perinatal mortality (p less than 0.05) [9].
  • The urine "oestriol ratio", the concentration of oestriol relative to the sum of the concentrations of oestrone and oestradiol, is inversely related to a population's breast-cancer rate [1].
  • In the luteal phase, the oestriol ratio of the youngest parous women was again distinctively raised and generally the oestriol ratios of parous women were higher than those of nulliparae [1].
  • In the follicular phase, the youngest parous women had an oestriol ratio 40% higher than, and significantly different from, the ratios of all other groups which were otherwise quite similar [1].

Chemical compound and disease context of estriol


Biological context of estriol


Anatomical context of estriol

  • That exercise may alter the neuroendocrine system is suggested by a delay in the ovulatory LH peak in spite of increased E3 excretion; moreover, less LH is excreted during the luteal phase [18].
  • In the absence of plasma proteins, estrone (E1) and estradiol (E2) were freely diffusible through the uterine capillaries, but influx was significantly reduced for estriol (E3) and estetrol [20].
  • Oestriol-stimulated synthesis of ribonucleic acid in the uterus of the immature rat [21].
  • When syngeneic bone marrow cells were transfused into E3-treated mice, focal hepatic hemopoiesis was increased further [22].
  • We tested the hypothesis that anthropometric markers and their relationship to umbilical cord leptin, cortisol and cortisone, DHEAs and oestriol differed between Caucasians and Asians at birth [23].

Associations of estriol with other chemical compounds


Gene context of estriol

  • Premarin induced a significant and progressive rise in E1 and E2 levels and in SHBG, whereas Ovestin induced no changes [29].
  • E3 stimulated the PR content by 7-10 times [30].
  • At 14 weeks a triple test (oestriol, J-HCG and alpha-fetoprotein) was normal and at 22 weeks a detailed ultrasound scan showed no congenital anomalies [31].
  • Oestriol treatment had no effect on dopaminergic markers in MPTP mice whereas oestrone prevented striatal DAT loss and the decrease of VMAT2 mRNA in the substantia nigra [32].
  • METHOD: The relationship between the maternal serum markers alphafetoprotein (AFP), human chorionic gonadotropin (HCG) and unconjugated oestriol (uE3), determined with the Beckman Coulter access reagents and maternal weight was investigated in a cohort of 752 Belgian women being screened for pregnancy associated with Down's syndrome [33].

Analytical, diagnostic and therapeutic context of estriol

  • Serum total oestriol was determined by radioimmunoassay every 6 h during intravenous beta-mimetic infusion (p less than 0.005) [34].
  • The subgroup of 25 children born to women with persistently low oestriol excretion during pregnancy showed a significant reduction in weight and head circumference at 6 years compared with the values in the control group and in the other children in the low-oestriol group [35].
  • Ninety-seven postmature pregnancies were monitored by amnioscopy or amniocentesis (to determine presence or absence of meconium), oxytocin challenge tests (OCT), 24-hour urinary oestriol estimations and fetal movement counts [36].
  • Total oestriol in maternal serum or plasma as measured by liquid chromatography [37].
  • Responsiveness to local E3 may correspond to improved cystoscopic findings as a consequence of increased bladder perfusion [38].


  1. Oestrogen profiles of parous and nulliparous women. Cole, P., MacMahon, B., Brown, J.B. Lancet (1976) [Pubmed]
  2. Low-potency oestrogen and risk of endometrial cancer: a case-control study. Weiderpass, E., Baron, J.A., Adami, H.O., Magnusson, C., Lindgren, A., Bergström, R., Correia, N., Persson, I. Lancet (1999) [Pubmed]
  3. Deletion of a DNA sequence in eight of nine families with X-linked ichthyosis (steroid sulphatase deficiency). Gillard, E.F., Affara, N.A., Yates, J.R., Goudie, D.R., Lambert, J., Aitken, D.A., Ferguson-Smith, M.A. Nucleic Acids Res. (1987) [Pubmed]
  4. Growth-promoting effect of oestriol in a lymphoma lacking oestrogen receptors. Kawatsu, R., Ezaki, T., Kotani, M., Akagi, M. Br. J. Cancer (1989) [Pubmed]
  5. Maternal serum unconjugated oestriol as an antenatal screening test for Down's syndrome. Wald, N.J., Cuckle, H.S., Densem, J.W., Nanchahal, K., Canick, J.A., Haddow, J.E., Knight, G.J., Palomaki, G.E. British journal of obstetrics and gynaecology. (1988) [Pubmed]
  6. Infant development following the use of intravenous nutrition to women with persistently low urinary oestriol excretion. Carne, R.J., Drew, J.H. The Australian & New Zealand journal of obstetrics & gynaecology. (1987) [Pubmed]
  7. The role of sex hormones in the mechanism of inhibited LH release in female patients with anorexia nervosa. Baranowska, B., Zgliczyński, S. Acta Endocrinol. (1982) [Pubmed]
  8. Second trimester maternal serum human chorionic gonadotropin and unconjugated oestriol levels in blacks and whites. Simpson, J.L., Elias, S., Morgan, C.D., Shulman, L., Umstot, E., Andersen, R.N. Lancet (1990) [Pubmed]
  9. Importance of abnormal glucose tolerance (hypoglycaemia and hyperglycaemia) in the aetiology of pre-eclampsia. Long, P.A., Abell, D.A., Beischer, N.A. Lancet (1977) [Pubmed]
  10. Enhancing effects of estrogens on endometrial carcinogenesis initiated by N-methyl-N-nitrosourea in ICR mice. Niwa, K., Murase, T., Furui, T., Morishita, S., Mori, H., Tanaka, T., Mori, H., Tamaya, T. Jpn. J. Cancer Res. (1993) [Pubmed]
  11. Second trimester amniotic fluid oestriol, dehydroepiandrosterone sulphate, and human chorionic gonadotrophin levels in Down's syndrome. Cuckle, H.S., Wald, N.J., Densem, J.W., Canick, J., Abell, K.B. British journal of obstetrics and gynaecology. (1991) [Pubmed]
  12. Eicosapentaenoic acid effect on hyperlipidemia in menopausal Japanese women. The Niigata Epadel Study Group. Kurabayashi, T., Okada, M., Tanaka, K. Obstetrics and gynecology. (2000) [Pubmed]
  13. An economic appraisal of alternative pre-natal screening programmes for Down's syndrome. Shackley, P., McGuire, A., Boyd, P.A., Dennis, J., Fitchett, M., Kay, J., Roche, M., Wood, P. Journal of public health medicine. (1993) [Pubmed]
  14. Increased saliva oestriol to progesterone ratio before preterm delivery: a possible predictor for preterm labor? Darne, J., McGarrigle, H.H., Lachelin, G.C. British medical journal (Clinical research ed.) (1987) [Pubmed]
  15. Enhancement of collagen-induced arthritis in female mice by estrogen receptor blockage. Jansson, L., Holmdahl, R. Arthritis Rheum. (2001) [Pubmed]
  16. Double-Stranded RNA-Dependent Protein Kinase Is Involved in 2-Methoxyestradiol-Mediated Cell Death of Osteosarcoma Cells. Shogren, K.L., Turner, R.T., Yaszemski, M.J., Maran, A. J. Bone Miner. Res. (2007) [Pubmed]
  17. Smith-Lemli-Opitz syndrome. II: A disorder of the fetal adrenals? McKeever, P.A., Young, I.D. J. Med. Genet. (1990) [Pubmed]
  18. Exercise induces two types of human luteal dysfunction: confirmation by urinary free progesterone. Beitins, I.Z., McArthur, J.W., Turnbull, B.A., Skrinar, G.S., Bullen, B.A. J. Clin. Endocrinol. Metab. (1991) [Pubmed]
  19. A reliable radiochromatographic assay technique for hepatic microsomal 16 alpha-hydroxylase activity towards oestrone 3-sulphate. Comparison between pigmented and non-pigmented mature guinea pigs. Tsoutsoulis, C.J., Hobkirk, R. Biochem. J. (1980) [Pubmed]
  20. Differential permeability of uterine and liver vascular beds to estrogens and estrogen conjugates. Verheugen, C., Pardridge, W.M., Judd, H.L., Chaudhuri, G. J. Clin. Endocrinol. Metab. (1984) [Pubmed]
  21. Oestriol-stimulated synthesis of ribonucleic acid in the uterus of the immature rat. Knowler, J.T. Biochem. J. (1978) [Pubmed]
  22. Effects of estrogen on hepatic hemopoiesis in the adult mouse. Hayama, T., Nawa, Y., Ezaki, T., Kotani, M. Exp. Hematol. (1983) [Pubmed]
  23. Different relationship between anthropometric markers and umbilical cord plasma leptin in Asian and Caucasian neonates. Yeung, L.P., Wong, A.C., Wang, X., Birmingham, C.L., Lewicka, S., Chanoine, J.P. Pediatr. Res. (2003) [Pubmed]
  24. Antenatal biochemical screening to predict low birthweight infants. Aickin, D.R., Duff, G.B., Evans, J.J., Legge, M. British journal of obstetrics and gynaecology. (1983) [Pubmed]
  25. Further characterization of estrogen binding to rat testis cytosol. Kühn-Velten, N., Bos, D., Staib, W. Steroids (1984) [Pubmed]
  26. The influence of abnormal glucose tolerance (hyperglycaemia and hypoglycaemia) on pregnancy outcome when oestriol excretion is subnormal. Abell, D.A., Beischer, N.A. British journal of obstetrics and gynaecology. (1975) [Pubmed]
  27. Longitudinal study of maternal plasma bioavailable testosterone and androstanediol glucuronide levels during pregnancy. Kerlan, V., Nahoul, K., Le Martelot, M.T., Bercovici, J.P. Clin. Endocrinol. (Oxf) (1994) [Pubmed]
  28. Does oestriol add to the beneficial effect of combined hormonal prophylaxis against early postmenopausal osteoporosis? Christiansen, C., Rødbro, P. British journal of obstetrics and gynaecology. (1984) [Pubmed]
  29. A group-comparative study of effects of Ovestin cream versus Premarin cream in post-menopausal women with vaginal atrophy. Luisi, M., Franchi, F., Kicovic, P.M. Maturitas. (1980) [Pubmed]
  30. Biological responses of tamoxifen in the fetal and newborn vagina and uterus of the guinea-pig and in the R-27 mammary cancer cell line. Pasqualini, J.R., Giambiagi, N., Sumida, C., Nguyen, B.L., Gelly, C., Mayrand, C., Lecerf, F. J. Steroid Biochem. (1986) [Pubmed]
  31. Ongoing normal pregnancy after transfer of zona-free blastocysts: implications for embryo transfer in the human. Fong, C.Y., Bongso, A., Ng, S.C., Anandakumar, C., Trounson, A., Ratnam, S. Hum. Reprod. (1997) [Pubmed]
  32. Oestrogens prevent loss of dopamine transporter (DAT) and vesicular monoamine transporter (VMAT2) in substantia nigra of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine mice. Jourdain, S., Morissette, M., Morin, N., Di Paolo, T. J. Neuroendocrinol. (2005) [Pubmed]
  33. Weight correction of MoM values: which method? Reynolds, T.M., Vranken, G., Van Nueten, J. J. Clin. Pathol. (2006) [Pubmed]
  34. Decrease of serum oestriol during intravenous hexoprenaline or salbutamol treatment. Haukkamaa, M., Gummerus, M. British journal of obstetrics and gynaecology. (1982) [Pubmed]
  35. Paediatric follow-up of pregnancies complicated by subnormal oestriol excretion. Wade, R.W., Searby, J., Pepperell, R.J., Kitchen, W.H. British journal of obstetrics and gynaecology. (1985) [Pubmed]
  36. Detection of fetal risk in postmaturity. Homburg, R., Ludomirski, A., Insler, V. British journal of obstetrics and gynaecology. (1979) [Pubmed]
  37. Total oestriol in maternal serum or plasma as measured by liquid chromatography. Andreolini, F., Borra, C., Di Corcia, A., Samperi, R., Raponi, G. J. Chromatogr. (1985) [Pubmed]
  38. Effects of local estrogen therapy on recurrent urinary tract infections in young females under oral contraceptives. Pinggera, G.M., Feuchtner, G., Frauscher, F., Rehder, P., Strasser, H., Bartsch, G., Herwig, R. Eur. Urol. (2005) [Pubmed]
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