Anordiol

Anordiol, or anordriol, also known as 2α,17α-diethynyl-A-nor-5α-androstane-2β,17β-diol, is a synthetic steroid-like mixed estrogen and antiestrogen and an active metabolite of anordrin, a postcoital contraceptive that is marketed and used in China.[1][2][3] Relative to anordrin, anordiol has similar but more potent actions.[1][2]

Anordiol
Clinical data
Other namesAnordriol; 2α,17α-Diethynyl-A-nor-5α-androstane-2β,17β-diol
Identifiers
IUPAC name
  • (2R,3aS,3bS,5aS,6R,8aS,8bR,10aS)-2,6-diethynyl-3a,5a-dimethyl-1,3,3b,4,5,7,8,8a,8b,9,10,10a-dodecahydroindeno[5,4-e]indene-2,6-diol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H30O2
Molar mass326.480 g·mol−1
3D model (JSmol)
SMILES
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CC[C@@H]4[C@@]3(C[C@](C4)(C#C)O)C
InChI
  • InChI=1S/C22H30O2/c1-5-21(23)13-15-7-8-16-17(19(15,3)14-21)9-11-20(4)18(16)10-12-22(20,24)6-2/h1-2,15-18,23-24H,7-14H2,3-4H3/t15-,16+,17-,18-,19-,20-,21+,22-/m0/s1
  • Key:HUUUMTTWAPMBMU-ZBJWQKIUSA-N

References
  1. Michael Oettel; Ekkehard Schillinger (6 December 2012). Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen. Springer Science & Business Media. pp. 545–. ISBN 978-3-642-60107-1.
  2. Chatterton RT, Berman C, Walters NN (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): 291–7. doi:10.1016/0010-7824(89)90061-9. PMID 2714089.
  3. Peters AJ, Wentz AC, Kazer RR, Jeyendran RS, Chatterton RT (1995). "Estrogenic and antiestrogenic activities of anordiol: a comparison of uterine and vaginal responses with those of clomiphene citrate". Contraception. 52 (3): 195–202. doi:10.1016/0010-7824(95)00151-y. PMID 7587192.



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