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]
Quick Facts Clinical data, Trade names ...
Anordrin |
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Trade names | Zi Yun (with mifepristone) |
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Other names | AF-53; α-Anordrin; Anordrine; 2α,17α-Diethynyl-A-nor-5α-androstane-2β,17β-diol dipropionate |
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Routes of administration | By mouth[1] |
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Drug class | Selective estrogen receptor modulator |
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Metabolites | Anordiol |
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[(2R,3aS,3bS,5aS,6R,8aS,8bR,10aS)-2,6-diethynyl-3a,5a-dimethyl-2-propanoyloxy-1,3,3b,4,5,7,8,8a,8b,9,10,10a-dodecahydroindeno[5,4-e]inden-6-yl] propanoate
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Formula | C28H38O4 |
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Molar mass | 438.608 g·mol−1 |
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CCC(=O)O[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(C[C@](C4)(C#C)OC(=O)CC)C)C)C#C
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InChI=1S/C28H38O4/c1-7-23(29)31-27(9-3)17-19-11-12-20-21(25(19,5)18-27)13-15-26(6)22(20)14-16-28(26,10-4)32-24(30)8-2/h3-4,19-22H,7-8,11-18H2,1-2,5-6H3/t19-,20+,21-,22-,25-,26-,27+,28-/m0/s1 Key:NOECSYBNZHIVHW-LKADTRSGSA-N
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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
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". Scientia Sinica. 18 (2): 262–270. PMID 808850.
Flynn AM, Lynch SS, Docker M, Morris R (6 December 2012). "Clinical, hormonal, and ultrasonic indicators of returning fertility after childbirth". In Harrison RF, Bonnar J, Thompson W (eds.). 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–. doi:10.1007/978-94-015-1308-1_31. ISBN 978-94-015-1308-1.
Xiao B (January 1997). "Abortion and emergency contraception: Chinese experience". Chinese Medical Journal. 110 (1): 36–42. PMID 9594319.
Han X, Weng L, Xiao B (September 1996). "[Emergency contraception with mifepristone and anordrin]". Zhonghua Fu Chan Ke Za Zhi (in Chinese). 31 (9): 526–529. PMID 9275422.
Sang G, Shao Q, Zhang L (June 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): 331–334. PMID 11360607.
Mehta RR, Jenco JM, Chatterton RT (December 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): 679–691. doi:10.1016/0039-128x(81)90086-6. PMID 7336465. S2CID 54233192.
Mehta RR, Jenco JM, Chatterton RT, Venton D (July 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. S2CID 54412520.
Song S, Chen JK, He ML, Zuo SH, Fotherby K (November 1987). "Effect of Anordrin on serum levels of sex hormone binding globulin, caeruloplasmin and ovarian function". Contraception. 36 (5): 541–548. doi:10.1016/0010-7824(87)90006-0. PMID 3447815.
Russeau GG, Quivy JI (April 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): 383–392. doi:10.1016/0039-128x(81)90040-4. PMID 6894653. S2CID 36863260.
Chatterton RT, Berman C, Walters NN (March 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): 291–297. doi:10.1016/0010-7824(89)90061-9. PMID 2714089.