Anordrin: Difference between revisions
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| 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 = |
| 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> |
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| class = [[Selective estrogen receptor modulator]] |
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'''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| |
'''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 }}</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> |
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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 = |
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> |
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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>{{ |
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 | 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}}}} |
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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=" |
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}} |
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==See also== |
== See also == |
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* [[List of selective estrogen receptor modulators]] |
* [[List of selective estrogen receptor modulators]] |
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==References== |
== References == |
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{{Reflist|30em}} |
{{Reflist|30em}} |
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{{Estrogens and antiestrogens}} |
{{Estrogens and antiestrogens}} |
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[[Category:Selective estrogen receptor modulators]] |
[[Category:Selective estrogen receptor modulators]] |
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[[Category:Synthetic estrogens]] |
[[Category:Synthetic estrogens]] |
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{{Genito-urinary-drug-stub}} |
{{Genito-urinary-drug-stub}} |
Revision as of 07:39, 27 November 2023
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 | |
| |
CAS Number | |
PubChem CID | |
ChemSpider | |
UNII | |
CompTox Dashboard (EPA) | |
Chemical and physical data | |
Formula | C28H38O4 |
Molar mass | 438.608 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
- ^ a b 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.
- ^ a b c d 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ a b Xiao B (January 1997). "Abortion and emergency contraception: Chinese experience". Chinese Medical Journal. 110 (1): 36–42. PMID 9594319.
- ^ "Anordrin". Drugs.com.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ a b 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.
- ^ 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.
- ^ a b c 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. Retrieved 2023-11-02.