Anordrin

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]

Trade namesZi Yun (with mifepristone)

Other namesAF-53; α-Anordrin; Anordrine; 2α,17α-Diethynyl-A-nor-5α-androstane-2β,17β-diol dipropionate

Routes of
administrationBy mouth^[1]

Drug classSelective estrogen receptor modulator

Quick facts Clinical data, Trade names ...

Anordrin
Clinical data

Trade names	Zi Yun (with mifepristone)
Other names	AF-53; α-Anordrin; Anordrine; 2α,17α-Diethynyl-A-nor-5α-androstane-2β,17β-diol dipropionate
Routes of administration	By mouth^[1]
Drug class	Selective estrogen receptor modulator
Pharmacokinetic data
Metabolites	Anordiol
Identifiers
IUPAC name [(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
CAS Number	56470-64-5
PubChem CID	6917889
ChemSpider	5293109
UNII	6R25F2A061
CompTox Dashboard (EPA)	DTXSID40872682
Chemical and physical data
Formula	C₂₈H₃₈O₄
Molar mass	438.608 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES 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
InChI 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

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

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". Scientia Sinica. 18 (2): 262–270. PMID 808850.
[2]
Oettel M (6 December 2012). "Estrogens and Antiestrogens in the Male". In Oettel M, Schillinger E (eds.). 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]
Haspels A (6 December 2012). "Post-coital Interception". In Runnebaum BC, Rabe T, Kiesel L (eds.). Female Contraception: Update and Trends. Springer Science & Business Media. pp. 377–. ISBN 978-3-642-73790-9.
[4]
Bell MR, Christiansen RG, Schane Jr HP (January 1979). "Chemical control of fertility.". In Weisbach JA (ed.). Annual Reports in Medicinal Chemistry. Vol. 14. Academic Press. pp. 168–177. doi:10.1016/S0065-7743(08)61361-5. ISBN 9780120405145.
[5]
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.
[6]
Liu CQ, Chen BL, Shen SR, Zhang GZ, Dai MZ (September 1985). "Effects of anordrin and its analogue on antifertility". Contraception. 32 (3): 301–309. doi:10.1016/0010-7824(85)90053-8. PMID 3841308.
[7]
Xiao B (January 1997). "Abortion and emergency contraception: Chinese experience". Chinese Medical Journal. 110 (1): 36–42. PMID 9594319.
[8]
"Anordrin". Drugs.com.
[9]
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.
[10]
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.
[11]
Harper MJ (14 January 2004). "Antiandrogens". In Glasser SR, Aplin JD, Giudice LC, Tabibzadeh S (eds.). The Endometrium. CRC Press. pp. 711–. ISBN 978-0-203-21903-4.
[12]
Chang MC (6 December 2012). "My Life with Mammalian Eggs". In Glasser SR, Bullock DW (eds.). Cellular and Molecular Aspects of Implantation. Springer Science & Business Media. pp. 31–. doi:10.1007/978-1-4613-3180-3_2. ISBN 978-1-4613-3180-3.
[13]
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.
[14]
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.
[15]
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.
[16]
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.
[17]
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.
[18]
Mehta RR, Chatterton RT (March 1991). "Antiovulatory action of anordrin in the cynomolgus monkey (Macaca fascicularis)". Advances in Contraception. 7 (1): 21–28. doi:10.1007/bf01850715. PMID 1872194. S2CID 38597111.
[19]
Rodriguez SM, ed. (2023). "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. pp. 167–203. doi:10.1017/9781009019880.007. ISBN 978-1-00-901988-0. OCLC 1366057905. Retrieved 2023-11-02.

See also

References

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