| 词条 | Anordrin |
| 释义 |
| Verifiedfields = | Watchedfields = | verifiedrevid = | 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 | image = Anordrin.svg | width = 250px | tradename = Zi Yun (with mifepristone) | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = By mouth[1] | class = Selective estrogen receptor modulator | bioavailability = | protein_bound = | metabolism = | metabolites = Anordiol | elimination_half-life = | excretion = | CAS_number_Ref = | CAS_number = 56470-64-5 | CAS_supplemental = | 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 | C=28 | H=38 | O=4 | molecular_weight = 438.599 g/mol | 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, 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.[8] The drug is marketed in a combination formulation with mifepristone under the brand name Zi Yun.[9][10][11] Anordrin has not been studied for use or marketed outside of China.[12] It has been used in China since the 1970s.[13][14] Anordrin has both weak estrogenic and antiestrogenic activity.[2][15][16][17] It binds to the estrogen receptor but does not bind to the androgen receptor or the progesterone receptor.[16][18] 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][19] 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.[20] See also
References1. ^{{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 = Sci. Sin. | volume = 18 | issue = 2 | pages = 262–70 | year = 1975 | pmid = 808850 | doi = | url = }} {{Estrogens and antiestrogens}}{{Estrogen receptor modulators}}{{Genito-urinary-drug-stub}}{{Steroid-stub}}2. ^1 2 3 {{cite book|author1=Michael Oettel|author2=Ekkehard Schillinger|title=Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen|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–}} 3. ^{{cite book|author1=Benno Clemens Runnebaum|author2=Thomas Rabe|author3=Ludwig Kiesel|title=Female Contraception: Update and Trends|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–}} 4. ^{{cite book|title=ANNUAL REPORTS IN MED CHEMISTRY V14 PPR|url=https://books.google.com/books?id=D4Cv8Ol4BV8C&pg=PA169|date=14 November 1979|publisher=Academic Press|isbn=978-0-08-058358-7|pages=169–}} 5. ^{{cite book|author1=R.F. Harrison|author2=J. Bonnar|author3=W. Thompson|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|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|pages=325–}} 6. ^{{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 = 301–9 | year = 1985 | pmid = 3841308 | doi = 10.1016/0010-7824(85)90053-8| url = }} 7. ^{{cite journal | vauthors = Xiao B | title = Abortion and emergency contraception: Chinese experience | journal = Chin. Med. J. | volume = 110 | issue = 1 | pages = 36–42 | year = 1997 | pmid = 9594319 | doi = | url = }} 8. ^{{cite journal | vauthors = Xiao B | title = Abortion and emergency contraception: Chinese experience | journal = Chin. Med. J. | volume = 110 | issue = 1 | pages = 36–42 | year = 1997 | pmid = 9594319 | doi = | url = }} 9. ^{{cite web | title = Anordrin | author = Drugs.com | url = https://www.drugs.com/international/anordrin.html}} 10. ^{{cite journal | vauthors = Han X, Weng L, Xiao B | title = [Emergency contraception with mifepristone and anordrin] | language = Chinese | journal = Zhonghua Fu Chan Ke Za Zhi | volume = 31 | issue = 9 | pages = 526–9 | year = 1996 | pmid = 9275422 | doi = | url = }} 11. ^{{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 = Chinese | journal = Zhonghua Fu Chan Ke Za Zhi | volume = 34 | issue = 6 | pages = 331–4 | year = 1999 | pmid = 11360607 | doi = | url = }} 12. ^{{cite book|author1=Stanley R. Glasser|author2=John D. Aplin|author3=Linda C. Giudice|author4=Siamak Tabibzadeh|title=The Endometrium|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–}} 13. ^{{cite book|author1=Stanley R. Glasser|author2=David W. Bullock|title=Cellular and Molecular Aspects of Implantation|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|pages=31–}} 14. ^{{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 = Sci. Sin. | volume = 18 | issue = 2 | pages = 262–70 | year = 1975 | pmid = 808850 | doi = | url = }} 15. ^{{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 = 679–91 | year = 1981 | pmid = 7336465 | doi = 10.1016/0039-128x(81)90086-6| url = }} 16. ^1 {{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 | year = 1982 | pmid = 6297127 | doi = 10.1016/0039-128x(82)90113-1| url = }} 17. ^{{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 = 541–8 | year = 1987 | pmid = 3447815 | doi = 10.1016/0010-7824(87)90006-0| url = }} 18. ^{{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 = 383–92 | year = 1981 | pmid = 6894653 | doi = 10.1016/0039-128x(81)90040-4 }} 19. ^{{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 = 291–7 | year = 1989 | pmid = 2714089 | doi = 10.1016/0010-7824(89)90061-9| url = }} 20. ^{{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 = 21–8 | year = 1991 | pmid = 1872194 | doi = 10.1007/bf01850715| url = }} 5 : Alkynes|Androstanes|Propionate esters|Selective estrogen receptor modulators|Synthetic estrogens |
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