Chemistry:Anordrin

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Short description: Chemical compound
Anordrin
Anordrin.svg
Clinical data
Trade namesZi Yun (with mifepristone)
Other namesAF-53; α-Anordrin; Anordrine; 2α,17α-Diethynyl-A-nor-5α-androstane-2β,17β-diol dipropionate
Routes of
administration		By mouth[1]
Drug classSelective estrogen receptor modulator
Pharmacokinetic data
MetabolitesAnordiol
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC28H38O4
Molar mass438.608 g·mol−1
3D model (JSmol)

Anordrin (former developmental code name AF-53), also known as 2α,17α-diethynyl-A-nor-5α-androstane-2β,17β-diol dipropionate, is a synthetic, steroidal selective estrogen receptor modulator (SERM) which is used in China as an emergency contraceptive.[2][3][4][5][6][7] It is the most commonly used emergency contraceptive in China.[7] The drug is marketed in a combination formulation with mifepristone under the brand name Zi Yun.[8][9][10] Anordrin has not been studied for use or marketed outside of China.[11] It has been used in China since the 1970s.[12][1]

Anordrin has both weak estrogenic and antiestrogenic activity.[2][13][14][15] It binds to the estrogen receptor but does not bind to the androgen receptor or the progesterone receptor.[14][16] 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, anordiol, with similar but more potent estrogenic activity.[2][17] The abortifacient effects of anordrin in animals are blocked by supplemental estradiol, suggesting that it is acting as an antiestrogen rather than an estrogen to exert its emergency contraceptive effects.[18]

The drug is also referred to as tanqinyao, "the Chinese vacation pill" or "the pill for visiting relatives," given that it is a recommended contraception method for couples[19] who have frequent sex within a short period, as may be the case for Chinese couples who live apart for most of the year due to work.[19]:175

Anordrin is not approved for use in the United States because each pill is near, or in excess of, the total monthly maximum allowable hormone dose in the American system.[19]:175

See also

References

  1. ↑ 1.0 1.1 "Pharmacological studies of a contraceptive drug anordrin". Scientia Sinica 18 (2): 262–270. 1975. PMID 808850. 
  2. ↑ 2.0 2.1 2.2 2.3 "Estrogens and Antiestrogens in the Male". Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen. Springer Science & Business Media. 6 December 2012. pp. 545–. ISBN 978-3-642-60107-1. https://books.google.com/books?id=wBvyCAAAQBAJ&pg=PA545. 
  3. ↑ "Post-coital Interception". Female Contraception: Update and Trends. Springer Science & Business Media. 6 December 2012. pp. 377–. ISBN 978-3-642-73790-9. https://books.google.com/books?id=LtT6CAAAQBAJ&pg=PA377. 
  4. ↑ "Chemical control of fertility.". Annual Reports in Medicinal Chemistry. 14. Academic Press. January 1979. pp. 168–177. doi:10.1016/S0065-7743(08)61361-5. ISBN 9780120405145. https://books.google.com/books?id=D4Cv8Ol4BV8C&pg=PA169. 
  5. ↑ "Clinical, hormonal, and ultrasonic indicators of returning fertility after childbirth". 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. 6 December 2012. pp. 325–. doi:10.1007/978-94-015-1308-1_31. ISBN 978-94-015-1308-1. https://books.google.com/books?id=lhorBgAAQBAJ&pg=PT325. 
  6. ↑ "Effects of anordrin and its analogue on antifertility". Contraception 32 (3): 301–309. September 1985. doi:10.1016/0010-7824(85)90053-8. PMID 3841308. 
  7. ↑ 7.0 7.1 "Abortion and emergency contraception: Chinese experience". Chinese Medical Journal 110 (1): 36–42. January 1997. PMID 9594319. 
  8. ↑ "Anordrin". Drugs.com. https://www.drugs.com/international/anordrin.html. 
  9. ↑ "[Emergency contraception with mifepristone and anordrin]" (in zh). Zhonghua Fu Chan Ke Za Zhi 31 (9): 526–529. September 1996. PMID 9275422. 
  10. ↑ "[A randomized multicentre clinical trial on different doses of mifepristone alone and in combination with anordrin as emergency contraception]" (in zh). Zhonghua Fu Chan Ke Za Zhi 34 (6): 331–334. June 1999. PMID 11360607. 
  11. ↑ "Antiandrogens". The Endometrium. CRC Press. 14 January 2004. pp. 711–. ISBN 978-0-203-21903-4. https://books.google.com/books?id=HYO9BwAAQBAJ&pg=PA711. 
  12. ↑ "My Life with Mammalian Eggs". Cellular and Molecular Aspects of Implantation. Springer Science & Business Media. 6 December 2012. pp. 31–. doi:10.1007/978-1-4613-3180-3_2. ISBN 978-1-4613-3180-3. https://books.google.com/books?id=iknTBwAAQBAJ&pg=PA31. 
  13. ↑ "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): 679–691. December 1981. doi:10.1016/0039-128x(81)90086-6. PMID 7336465. 
  14. ↑ 14.0 14.1 "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. July 1982. doi:10.1016/0039-128x(82)90113-1. PMID 6297127. 
  15. ↑ "Effect of Anordrin on serum levels of sex hormone binding globulin, caeruloplasmin and ovarian function". Contraception 36 (5): 541–548. November 1987. doi:10.1016/0010-7824(87)90006-0. PMID 3447815. 
  16. ↑ "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): 383–392. April 1981. doi:10.1016/0039-128x(81)90040-4. PMID 6894653. 
  17. ↑ "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): 291–297. March 1989. doi:10.1016/0010-7824(89)90061-9. PMID 2714089. 
  18. ↑ "Antiovulatory action of anordrin in the cynomolgus monkey (Macaca fascicularis)". Advances in Contraception 7 (1): 21–28. March 1991. doi:10.1007/bf01850715. PMID 1872194. 
  19. ↑ 19.0 19.1 19.2 "The Rise and Demise of the One Child Policy, 1979–2015". Reproductive Realities in Modern China: Birth Control and Abortion, 1911–2021. Cambridge Studies in the History of the People's Republic of China. Cambridge: Cambridge University Press. 2023. pp. 167–203. doi:10.1017/9781009019880.007. ISBN 978-1-00-901988-0. OCLC 1366057905. https://www.cambridge.org/core/books/reproductive-realities-in-modern-china/rise-and-demise-of-the-one-child-policy-19792015/1DA651C7B5A4BF8F85BCDF3CBF1F95D4. Retrieved 2023-11-02. 



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