Anordrin

Anordrin
Clinical data
Routes of
administration		 Oral[1]
Identifiers
Synonyms α-Anordrin; anordrine
CAS Number 56470-64-5
PubChem (CID) 6917889
ChemSpider 97177
Chemical and physical data
Formula C28H38O4
Molar mass 438.59892 g/mol
3D model (Jmol) Interactive image

Anordrin (former developmental code name AF-53), also known as 2α,17α-diethynyl-A-nor-5α-androstane-2β,17β-diol dipropionate, is a synthetic, steroid-like estrogen that is used in China as a postcoital contraceptive.[2][3][4][5][6][7] It is marketed in a combination formulation with mifepristone under the brand name Zi Yun.[8][9][10] Anordrin is a selective estrogen receptor modulator, with both weak estrogenic and antiestrogenic properties.[2][11][12][13] It binds to the estrogen receptor but does not bind to the androgen receptor or the progesterone receptor.[12][14] In animals, anordrin has antigonadotropic effects, and in male animals, inhibits spermatogenesis and causes atrophy of the epididymis, prostate, and seminal vesicles.[2] It produces a dihydroxylated active metabolite, anordriol, with similar but more potent estrogenic actions.[2][15] The abortifacient actions of anordrin in animals are blocked by supplemental estradiol, indicating that it is acting as an antiestrogen rather than an estrogen to exert its effects.[16]

See also

References

  1. ↑ Chih-ping K, Ming-kang C, Hsiu-chüan C, Shih-hsing C, Ta-wei P, Kang T (1975). "Pharmacological studies of a contraceptive drug anordrin". Sci. Sin. 18 (2): 262–70. PMID 808850.
  2. 1 2 3 4 Michael Oettel; Ekkehard Schillinger (6 December 2012). Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen. Springer Science & Business Media. pp. 545–. ISBN 978-3-642-60107-1.
  3. ↑ Benno Clemens Runnebaum; Thomas Rabe; Ludwig Kiesel (6 December 2012). Female Contraception: Update and Trends. Springer Science & Business Media. pp. 377–. ISBN 978-3-642-73790-9.
  4. ↑ ANNUAL REPORTS IN MED CHEMISTRY V14 PPR. Academic Press. 14 November 1979. pp. 169–. ISBN 978-0-08-058358-7.
  5. ↑ R.F. Harrison; J. Bonnar; W. Thompson (6 December 2012). Fertility and Sterility: The Proceedings of the XIth World Congress on Fertility and Sterility, Dublin, June 1983, held under the Auspices of the International Federation of Fertility Societies. Springer Science & Business Media. pp. 325–. ISBN 978-94-015-1308-1.
  6. ↑ Liu CQ, Chen BL, Shen SR, Zhang GZ, Dai MZ (1985). "Effects of anordrin and its analogue on antifertility". Contraception. 32 (3): 301–9. doi:10.1016/0010-7824(85)90053-8. PMID 3841308.
  7. ↑ Xiao B (1997). "Abortion and emergency contraception: Chinese experience". Chin. Med. J. 110 (1): 36–42. PMID 9594319.
  8. ↑ Drugs.com. "Anordrin".
  9. ↑ Han X, Weng L, Xiao B (1996). "[Emergency contraception with mifepristone and anordrin]". Zhonghua Fu Chan Ke Za Zhi (in Chinese). 31 (9): 526–9. PMID 9275422.
  10. ↑ Sang G, Shao Q, Zhang L (1999). "[A randomized multicentre clinical trial on different doses of mifepristone alone and in combination with anordrin as emergency contraception]". Zhonghua Fu Chan Ke Za Zhi (in Chinese). 34 (6): 331–4. PMID 11360607.
  11. ↑ Mehta RR, Jenco JM, Chatterton RT (1981). "Antiestrogenic and antifertility actions of Anordrin (2 alpha, 17 alpha-diethynyl-A-nor-5 alpha-androstane-2 beta, 17 beta-diol 2,17-dipropionate)". Steroids. 38 (6): 679–91. doi:10.1016/0039-128x(81)90086-6. PMID 7336465.
  12. 1 2 Mehta RR, Jenco JM, Chatterton RT, Venton D (1982). "Antagonism of the actions of estrogens, androgens and progesterone by anordrin (2 alpha, 17 alpha-diethynyl-A-nor-5 alpha-androstane-2 beta, 17 beta-diol dipropionate)". Steroids. 40 (1): 65–80. doi:10.1016/0039-128x(82)90113-1. PMID 6297127.
  13. ↑ Song S, Chen JK, He ML, Zuo SH, Fotherby K (1987). "Effect of Anordrin on serum levels of sex hormone binding globulin, caeruloplasmin and ovarian function". Contraception. 36 (5): 541–8. doi:10.1016/0010-7824(87)90006-0. PMID 3447815.
  14. ↑ Russeau GG, Quivy JI (1981). "Interaction of A-nor, A, 19-dinor, and A-homo-5 alpha-androstane derivatives with the androgen receptor and the epididymal androgen-binding protein". Steroids. 37 (4): 383–92. PMID 6894653.
  15. ↑ Chatterton RT, Berman C, Walters NN (1989). "Anti-uterotrophic and folliculostatic activities of anordiol (2 alpha,17 alpha-diethynyl-A-nor-5 alpha-androstane-2 beta,17 beta-diol)". Contraception. 39 (3): 291–7. doi:10.1016/0010-7824(89)90061-9. PMID 2714089.
  16. ↑ Mehta RR, Chatterton RT (1991). "Antiovulatory action of anordrin in the cynomolgus monkey (Macaca fascicularis)". Advances in Contraception : the Official Journal of the Society for the Advancement of Contraception. 7 (1): 21–8. PMID 1872194.



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