Doisynoestrol

Doisynoestrol (brand names Fenocyclin, Surestrine, Surestryl; former developmental code name RS-2874), also known as fenocycline, as well as cis-bisdehydrodoisynolic acid 7-methyl ether (BDDA ME), is a synthetic nonsteroidal estrogen of the doisynolic acid group that is no longer marketed.[1][2] It is a methyl ether of bisdehydrodoisynolic acid.[1] Doisynoestrol was described in the literature in 1945.[1] It has about 0.02% of the relative binding affinity of estradiol for the estrogen receptor.[3]

Doisynoestrol
Clinical data
Trade namesFenocyclin, Surestrine, Surestryl
Other namesDiosynestrol; Fenocycline; Fenocyclin; Phenocyclin; RS-2874; Dehydrofolliculinic acid; cis-Bisdehydrodoisynolic acid 7-methyl ether; BDDA ME; NSC-56846; NSC-122041
Routes of
administration		By mouth
Drug classNonsteroidal estrogen
Identifiers
IUPAC name
  • 1-Ethyl-7-methoxy-2-methyl-3,4-dihydro-1H-phenanthrene-2-carboxylic acid
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H22O3
Molar mass298.382 g·mol−1
3D model (JSmol)
SMILES
  • CCC1C2=C(CCC1(C)C(=O)O)C3=C(C=C2)C=C(C=C3)OC
InChI
  • InChI=1S/C19H22O3/c1-4-17-16-7-5-12-11-13(22-3)6-8-14(12)15(16)9-10-19(17,2)18(20)21/h5-8,11,17H,4,9-10H2,1-3H3,(H,20,21)
  • Key:HZZSXUIUESWVSS-UHFFFAOYSA-N

See also

References
  1. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 465–. ISBN 978-1-4757-2085-3.
  2. Herbai G (October 1971). "Separation of growth inhibiting potency from oestrogenicity in different weak oestrogenic drugs of various chemical structures". Acta Endocrinologica. 68 (2): 249–63. doi:10.1530/acta.0.0680249. PMID 5171465.
  3. Blair RM, Fang H, Branham WS, Hass BS, Dial SL, Moland CL, Tong W, Shi L, Perkins R, Sheehan DM (March 2000). "The estrogen receptor relative binding affinities of 188 natural and xenochemicals: structural diversity of ligands". Toxicol Sci. 54 (1): 138–53. doi:10.1093/toxsci/54.1.138. PMID 10746941.



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