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Chemical Compound Review

Nemestran     (8S,13R,14S,17S)-13-ethyl-17- ethynyl-17...

Synonyms: Dimetrose, Tridomose, Dimetriose, Gestrigone, Gestrinona, ...
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Disease relevance of Dimetriose


Psychiatry related information on Dimetriose


High impact information on Dimetriose

  • Discovery, biosynthesis, and structure elucidation of metabolites of a doping agent and a direct analogue, tetrahydrogestrinone and gestrinone, using human hepatocytes [8].
  • Due to high structure similarity, both THG and gestrinone had an analogous in vitro metabolic pathway leading to successive addition of a hydroxyl and a beta-glucuronic acid at C-18 [8].
  • At 3 months of treatment, the endometria of the danazol-treated patients were more atrophic than those of the women who received gestrinone [1].
  • The ultrastructural investigation demonstrated complete involution of the cytoplasmic organelles with cytoplasmic collapse in glandular cells of patients treated with danazol, whereas in the gestrinone group degeneration phenomena were observed in both nucleus and cytoplasm [1].
  • THG was synthesized by hydrogenation of gestrinone and characterized by mass spectrometry and NMR spectroscopy [9].

Chemical compound and disease context of Dimetriose


Biological context of Dimetriose

  • OBJECTIVE: To study some of the metabolic effects of oral gestrinone on plasma lipoprotein risk markers for cardiovascular disease and on bone density, a risk marker for osteoporosis [13].
  • The common OR for pregnancy after ovulation suppression (MPA, gestrinone, or GnRH agonist) versus danazol was also nonsignificant: 1.07 [14].
  • The results of this study showed that gestrinone significantly inhibited macrophage phagocytosis at the concentrations of 10(-8), 3 x 10(-8) and 10(-7) M [15].
  • It is hypothesized that incomplete endometrial involution could be due to differences in gestrinone pharmacokinetics in individual patients, in the quality and/or quantity of endometrial cytosolic receptors for sex steroids, or in endocrine compensation to administration of the drug [16].
  • The histology and ultrastructure of small endometriotic lesions were studied in 19 patients before and after hormonal therapy with the anti-progesterone steroid R 2323 (Gestrinone) [17].

Anatomical context of Dimetriose


Associations of Dimetriose with other chemical compounds


Gene context of Dimetriose

  • The mean SHBG binding capacity in patients treated with danazol (400 mg/d, n = 7) and gestrinone (5 mg/week, n = 7) fell from 66.9 and 56.4 nmol/l to 36.1 and 28.1 nmol/l, after 1 week's treatment and to 11.1 and 7.1 nmol/l after 4 weeks respectively [21].
  • Gestrinone's more avid affinity for estrogen receptor may be the reason for the ability to use a lower clinical dose of gestrinone [11].
  • Gestrinone suppressed the 3 beta-hydroxysteroid dehydrogenase activity and increased activities of 17 alpha-hydroxylase, 17, 20-lyase and aromatase in ovaries stimulated by 5 IU of PMS, while MPA suppressed activities of 17 alpha-hydroxylase and aromatase in these ovaries [24].

Analytical, diagnostic and therapeutic context of Dimetriose


  1. Endometrial patterns during therapy with danazol or gestrinone for endometriosis: structural and ultrastructural study. Marchini, M., Fedele, L., Bianchi, S., Di Nola, G., Nava, S., Vercellini, P. Hum. Pathol. (1992) [Pubmed]
  2. Long-term treatment of leiomyomas with gestrinone. Coutinho, E.M., Gonçalves, M.T. Fertil. Steril. (1989) [Pubmed]
  3. Gestrinone versus danazol in the treatment of endometriosis. Fedele, L., Bianchi, S., Viezzoli, T., Arcaini, L., Candiani, G.B. Fertil. Steril. (1989) [Pubmed]
  4. Gestrinone in the treatment of uterine leiomyomata: effects on uterine blood supply. La Marca, A., Giulini, S., Vito, G., Orvieto, R., Volpe, A., Jasonni, V.M. Fertil. Steril. (2004) [Pubmed]
  5. Gestrinone in the treatment of menorrhagia. Turnbull, A.C., Rees, M.C. British journal of obstetrics and gynaecology. (1990) [Pubmed]
  6. Regression of uterine leiomyomas after treatment with gestrinone, an antiestrogen, antiprogesterone. Coutinho, E.M., Boulanger, G.A., Gonçalves, M.T. Am. J. Obstet. Gynecol. (1986) [Pubmed]
  7. Gestrinone versus danazol as preoperative treatment for hysteroscopic surgery: a prospective, randomized evaluation. Triolo, O., De Vivo, A., Benedetto, V., Falcone, S., Antico, F. Fertil. Steril. (2006) [Pubmed]
  8. Discovery, biosynthesis, and structure elucidation of metabolites of a doping agent and a direct analogue, tetrahydrogestrinone and gestrinone, using human hepatocytes. Lévesque, J.F., Templeton, E., Trimble, L., Berthelette, C., Chauret, N. Anal. Chem. (2005) [Pubmed]
  9. Tetrahydrogestrinone: discovery, synthesis, and detection in urine. Catlin, D.H., Sekera, M.H., Ahrens, B.D., Starcevic, B., Chang, Y.C., Hatton, C.K. Rapid Commun. Mass Spectrom. (2004) [Pubmed]
  10. Effect of gestrinone in endometriosis tissue and endometrium. Kauppila, A., Isomaa, V., Rönnberg, L., Vierikko, P., Vihko, R. Fertil. Steril. (1985) [Pubmed]
  11. Gestrinone (R2323) binding to steroid receptors in human uterine endometrial cytosol. Tamaya, T., Fujimoto, J., Watanabe, Y., Arahori, K., Okada, H. Acta obstetricia et gynecologica Scandinavica. (1986) [Pubmed]
  12. Ovulation suppression for endometriosis. Hughes, E., Fedorkow, D., Collins, J., Vandekerckhove, P. Cochrane database of systematic reviews (Online) (2000) [Pubmed]
  13. A randomized comparative study of the metabolic effects of two regimens of gestrinone in the treatment of endometriosis. Worthington, M., Irvine, L.M., Crook, D., Lees, B., Shaw, R.W., Stevenson, J.C. Fertil. Steril. (1993) [Pubmed]
  14. A quantitative overview of controlled trials in endometriosis-associated infertility. Hughes, E.G., Fedorkow, D.M., Collins, J.A. Fertil. Steril. (1993) [Pubmed]
  15. Gestrinone inhibits macrophage function and mitogen-stimulated lymphocyte proliferation in vitro. Viganò, P., Magri, B., Di Blasio, A.M., Busacca, M., Vignali, M. J. Reprod. Immunol. (1994) [Pubmed]
  16. Evaluation of histological and ultrastructural aspects of endometrium during treatment with gestrinone in women with amenorrhea or spotting. Fedele, L., Marchini, M., Baglioni, A., Dell'Antonio, G., Motta, T. Acta obstetricia et gynecologica Scandinavica. (1990) [Pubmed]
  17. The response of human endometriotic implants to the anti-progesterone steroid R 2323: a histologic and ultrastructural study. Cornillie, F.J., Vasquez, G., Brosens, I. Pathol. Res. Pract. (1985) [Pubmed]
  18. The effect of a synthetic progestogen, ethylnorgestrienone, on hypothalamic-pituitary-ovarian function, cervical mucus, vaginal cytology, and endometrial morphology. Niaraki, M.A., Moghissi, K.S., Borin, K. Fertil. Steril. (1981) [Pubmed]
  19. The inhibitory effects of danazol, danazol metabolites, gestrinone, and testosterone on the growth of human endometrial cells in vitro. Rose, G.L., Dowsett, M., Mudge, J.E., White, J.O., Jeffcoate, S.L. Fertil. Steril. (1988) [Pubmed]
  20. Evaluation of progesterone and estrogen receptor expression in 15 meningiomas of dogs and cats. Adamo, P.F., Cantile, C., Steinberg, H. Am. J. Vet. Res. (2003) [Pubmed]
  21. A comparison of the effects of danazol and gestrinone on testosterone binding to sex hormone binding globulin in vitro and in vivo. Dowsett, M., Forbes, K.L., Rose, G.L., Mudge, J.E., Jeffcoate, S.L. Clin. Endocrinol. (Oxf) (1986) [Pubmed]
  22. Histologic study of ovarian endometriosis after hormonal therapy. Nisolle-Pochet, M., Casanas-Roux, F., Donnez, J. Fertil. Steril. (1988) [Pubmed]
  23. Comparative clinical trial of the progestins R-2323 and levonorgestrel administered by subdermal implants. Alvarez, F., Robertson, D.N., Montes de Oca, V., Sivin, I., Brache, V., Faundes, A. Contraception. (1978) [Pubmed]
  24. No inhibitory effects of gestrinone and medroxyprogesterone acetate on the estrogen production by ovaries of hypophysectomized rats stimulated by gonadotropins. Mizutani, T., Sakata, M., Miyake, A., Tanizawa, O., Terada, N., Matsumoto, K., Terakawa, N. Endocrinol. Jpn. (1992) [Pubmed]
  25. Multicentre study of gestrinone in cyclical breast pain. Peters, F. Lancet (1992) [Pubmed]
  26. Determination and excretion study of gestrinone in human urine by high performance liquid chromatography and gas chromatography/mass spectrometry. Kim, Y., Lee, Y., Kim, M., Yim, Y.H., Lee, W. Rapid Commun. Mass Spectrom. (2000) [Pubmed]
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