View source for Anordrin

{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = 
| Watchedfields = 
| verifiedrevid = 
| IUPAC_name = [(2''R'',3a''S'',3b''S'',5a''S'',6''R'',8a''S'',8b''R'',10a''S'')-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
| image = Anordrin.svg
| width = 250px

<!--Clinical data-->
| tradename = Zi Yun (with [[mifepristone]])
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category = 
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = 
| legal_UK = 
| legal_US = 
| legal_status = 
| routes_of_administration = [[Oral administration|By mouth]]<ref name="pmid808850">{{cite journal | vauthors = Chih-ping K, Ming-kang C, Hsiu-chüan C, Shih-hsing C, Ta-wei P, Kang T | title = Pharmacological studies of a contraceptive drug anordrin | journal = Scientia Sinica | volume = 18 | issue = 2 | pages = 262–270 | year = 1975 | pmid = 808850 }}</ref>
| class = [[Selective estrogen receptor modulator]]

<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = 
| metabolites = [[Anordiol]]
| elimination_half-life = 
| excretion = 

<!--Identifiers-->
| CAS_number_Ref = 
| CAS_number = 56470-64-5
| CAS_supplemental = 
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 6R25F2A061
| ATC_prefix = 
| ATC_suffix = 
| PubChem = 6917889
| DrugBank_Ref = 
| DrugBank = 
| ChemSpiderID_Ref = 
| ChemSpiderID = 5293109
| synonyms = AF-53; α-Anordrin; Anordrine; 2α,17α-Diethynyl-A-nor-5α-androstane-2β,17β-diol dipropionate

<!--Chemical data-->
| C=28 | H=38 | O=4
| 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
| StdInChI = 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
| StdInChIKey = NOECSYBNZHIVHW-LKADTRSGSA-N
}}

'''Anordrin''' (former developmental code name '''AF-53'''), also known as '''2α,17α-diethynyl-A-nor-5α-androstane-2β,17β-diol dipropionate''', is a [[synthetic compound|synthetic]], [[steroid]]al [[selective estrogen receptor modulator]] (SERM) which is used in [[China]] as an [[emergency contraception|emergency contraceptive]].<ref name="OettelSchillinger2012">{{cite book| vauthors = Oettel M | chapter = Estrogens and Antiestrogens in the Male | veditors = Oettel M, Schillinger E |title=Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen| chapter-url=https://books.google.com/books?id=wBvyCAAAQBAJ&pg=PA545|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-60107-1|pages=545–}}</ref><ref name="RunnebaumRabe2012">{{cite book| vauthors = Haspels A | chapter = Post-coital Interception | veditors = Runnebaum BC, Rabe T, Kiesel L |title=Female Contraception: Update and Trends| chapter-url = https://books.google.com/books?id=LtT6CAAAQBAJ&pg=PA377|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-73790-9|pages=377–}}</ref><ref>{{cite book| vauthors = Bell MR, Christiansen RG, Schane Jr HP | chapter = Chemical control of fertility. | veditors = Weisbach JA | title = Annual Reports in Medicinal Chemistry | date = January 1979 | volume = 14 | pages = 168–177 | publisher = Academic Press | chapter-url = https://books.google.com/books?id=D4Cv8Ol4BV8C&pg=PA169 | doi = 10.1016/S0065-7743(08)61361-5 | isbn = 9780120405145 }}</ref><ref name="HarrisonBonnar2012">{{cite book| vauthors = Flynn AM, Lynch SS, Docker M, Morris R | chapter = Clinical, hormonal, and ultrasonic indicators of returning fertility after childbirth | veditors = Harrison RF, Bonnar J, Thompson W |title=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| chapter-url=https://books.google.com/books?id=lhorBgAAQBAJ&pg=PT325|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-015-1308-1 | doi = 10.1007/978-94-015-1308-1_31 |pages=325–}}</ref><ref name="pmid3841308">{{cite journal | vauthors = Liu CQ, Chen BL, Shen SR, Zhang GZ, Dai MZ | title = Effects of anordrin and its analogue on antifertility | journal = Contraception | volume = 32 | issue = 3 | pages = 301–309 | date = September 1985 | pmid = 3841308 | doi = 10.1016/0010-7824(85)90053-8 }}</ref><ref name="pmid9594319">{{cite journal | vauthors = Xiao B | title = Abortion and emergency contraception: Chinese experience | journal = Chinese Medical Journal | volume = 110 | issue = 1 | pages = 36–42 | date = January 1997 | pmid = 9594319 }}</ref> It is the most commonly used emergency contraceptive in China.<ref name="pmid9594319">{{cite journal | vauthors = Xiao B | title = Abortion and emergency contraception: Chinese experience | journal = Chinese Medical Journal | volume = 110 | issue = 1 | pages = 36–42 | date = January 1997 | pmid = 9594319 }}</ref> The drug is marketed in a [[combination formulation]] with [[mifepristone]] under the brand name '''Zi Yun'''.<ref name="Drugs.com">{{cite web | title = Anordrin | work = Drugs.com | url = https://www.drugs.com/international/anordrin.html}}</ref><ref name="pmid9275422">{{cite journal | vauthors = Han X, Weng L, Xiao B | title = [Emergency contraception with mifepristone and anordrin] | language = zh | journal = Zhonghua Fu Chan Ke Za Zhi | volume = 31 | issue = 9 | pages = 526–529 | date = September 1996 | pmid = 9275422 }}</ref><ref name="pmid11360607">{{cite journal | vauthors = Sang G, Shao Q, Zhang L | title = [A randomized multicentre clinical trial on different doses of mifepristone alone and in combination with anordrin as emergency contraception] | language = zh | journal = Zhonghua Fu Chan Ke Za Zhi | volume = 34 | issue = 6 | pages = 331–334 | date = June 1999 | pmid = 11360607 }}</ref> Anordrin has not been studied for use or marketed outside of China.<ref name="GlasserAplin2004">{{cite book| vauthors = Harper MJ | chapter = Antiandrogens | veditors = Glasser SR, Aplin JD, Giudice LC, Tabibzadeh S |title=The Endometrium| chapter-url = https://books.google.com/books?id=HYO9BwAAQBAJ&pg=PA711|date=14 January 2004|publisher=CRC Press|isbn=978-0-203-21903-4|pages=711–}}</ref> It has been used in China since the 1970s.<ref name="GlasserBullock2012">{{cite book| vauthors = Chang MC | chapter = My Life with Mammalian Eggs | veditors = Glasser SR, Bullock DW |title=Cellular and Molecular Aspects of Implantation| chapter-url = https://books.google.com/books?id=iknTBwAAQBAJ&pg=PA31|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-1-4613-3180-3 | doi = 10.1007/978-1-4613-3180-3_2 |pages=31–}}</ref><ref name="pmid808850">{{cite journal | vauthors = Chih-ping K, Ming-kang C, Hsiu-chüan C, Shih-hsing C, Ta-wei P, Kang T | title = Pharmacological studies of a contraceptive drug anordrin | journal = Scientia Sinica | volume = 18 | issue = 2 | pages = 262–270 | year = 1975 | pmid = 808850 }}</ref>

Anordrin has both weak [[estrogen (medication)|estrogen]]ic and [[antiestrogen]]ic activity.<ref name="OettelSchillinger2012" /><ref name="pmid7336465">{{cite journal | vauthors = Mehta RR, Jenco JM, Chatterton RT | title = Antiestrogenic and antifertility actions of Anordrin (2 alpha, 17 alpha-diethynyl-A-nor-5 alpha-androstane-2 beta, 17 beta-diol 2,17-dipropionate) | journal = Steroids | volume = 38 | issue = 6 | pages = 679–691 | date = December 1981 | pmid = 7336465 | doi = 10.1016/0039-128x(81)90086-6 | s2cid = 54233192 }}</ref><ref name="pmid6297127">{{cite journal | vauthors = Mehta RR, Jenco JM, Chatterton RT, Venton D | title = 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) | journal = Steroids | volume = 40 | issue = 1 | pages = 65–80 | date = July 1982 | pmid = 6297127 | doi = 10.1016/0039-128x(82)90113-1 | s2cid = 54412520 }}</ref><ref name="pmid3447815">{{cite journal | vauthors = Song S, Chen JK, He ML, Zuo SH, Fotherby K | title = Effect of Anordrin on serum levels of sex hormone binding globulin, caeruloplasmin and ovarian function | journal = Contraception | volume = 36 | issue = 5 | pages = 541–548 | date = November 1987 | pmid = 3447815 | doi = 10.1016/0010-7824(87)90006-0 }}</ref> It binds to the [[estrogen receptor]] but does not bind to the [[androgen receptor]] or the [[progesterone receptor]].<ref name="pmid6297127" /><ref name="pmid6894653">{{cite journal | vauthors = Russeau GG, Quivy JI | title = Interaction of A-nor, A, 19-dinor, and A-homo-5 alpha-androstane derivatives with the androgen receptor and the epididymal androgen-binding protein | journal = Steroids | volume = 37 | issue = 4 | pages = 383–392 | date = April 1981 | pmid = 6894653 | doi = 10.1016/0039-128x(81)90040-4 | s2cid = 36863260 }}</ref> In animals, anordrin has [[antigonadotropic]] effects, and in male animals, inhibits [[spermatogenesis]] and causes [[atrophy]] of the [[epididymis]], [[prostate]], and [[seminal vesicle]]s.<ref name="OettelSchillinger2012" /> It produces a dihydroxylated [[active metabolite]], [[anordiol]], with similar but more potent estrogenic activity.<ref name="OettelSchillinger2012" /><ref name="pmid2714089">{{cite journal | vauthors = Chatterton RT, Berman C, Walters NN | title = Anti-uterotrophic and folliculostatic activities of anordiol (2 alpha,17 alpha-diethynyl-A-nor-5 alpha-androstane-2 beta,17 beta-diol) | journal = Contraception | volume = 39 | issue = 3 | pages = 291–297 | date = March 1989 | pmid = 2714089 | doi = 10.1016/0010-7824(89)90061-9 }}</ref> The [[abortifacient]] effects of anordrin in animals are blocked by supplemental [[estradiol (medication)|estradiol]], suggesting that it is acting as an antiestrogen rather than an estrogen to exert its emergency contraceptive effects.<ref name="pmid1872194">{{cite journal | vauthors = Mehta RR, Chatterton RT | title = Antiovulatory action of anordrin in the cynomolgus monkey (Macaca fascicularis) | journal = Advances in Contraception | volume = 7 | issue = 1 | pages = 21–28 | date = March 1991 | pmid = 1872194 | doi = 10.1007/bf01850715 | s2cid = 38597111 }}</ref>

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<ref name = "Rodriguez_2023">{{cite book | chapter = The Rise and Demise of the One Child Policy, 1979–2015 |date=2023 | chapter-url = https://www.cambridge.org/core/books/reproductive-realities-in-modern-china/rise-and-demise-of-the-one-child-policy-19792015/1DA651C7B5A4BF8F85BCDF3CBF1F95D4 | doi = 10.1017/9781009019880.007 | isbn = 978-1-00-901988-0 | oclc = 1366057905 | title = Reproductive Realities in Modern China: Birth Control and Abortion, 1911–2021 |pages=167–203 | veditors = Rodriguez SM |access-date=2023-11-02 |series=Cambridge Studies in the History of the People's Republic of China |place=Cambridge |publisher=Cambridge University Press }}</ref> 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.<ref name = "Rodriguez_2023" />{{rp|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.<ref name = "Rodriguez_2023" />{{rp|175}}

== See also ==
* [[List of selective estrogen receptor modulators]]

== References ==
{{Reflist|30em}}

{{Estrogens and antiestrogens}}
{{Estrogen receptor modulators}}

[[Category:Ethynyl compounds]]
[[Category:Androstanes]]
[[Category:Propionate esters]]
[[Category:Selective estrogen receptor modulators]]
[[Category:Synthetic estrogens]]

{{Genito-urinary-drug-stub}}
{{Steroid-stub}}