Nilestriol

Nilestriol (INN) (brand name Wei Ni An; developmental code name LY-49825), also known as nylestriol (USAN, BAN), is a synthetic estrogen which was patented in 1971[1] and is marketed in China.[2][3] It is the 3-cyclopentyl ether of ethinylestriol, and is also known as ethinylestriol cyclopentyl ether (EE3CPE).[4] Nilestriol is a prodrug of ethinylestriol, and is a more potent estrogen in comparison.[4] It is described as a slowly-metabolized, long-acting estrogen and derivative of estriol.[5][6] Nilestriol was assessed in combination with levonorgestrel for the potential treatment of postmenopausal osteoporosis, but this formulation ultimately was not marketed.[7]

Nilestriol
Clinical data
Trade namesWei Ni An
Other namesNylestriol; LY-49825; Ethinylestriol cyclopentyl ether; EE3CPE; 17α-Ethynylestriol 3-cyclopentyl ether
Routes of
administration		By mouth
Drug classEstrogen; Estrogen ether
Identifiers
IUPAC name
  • (8R,9S,13S,14S,16R,17R)-3-cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC25H32O3
Molar mass380.528 g·mol−1
3D model (JSmol)
SMILES
  • C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H]([C@]2(C#C)O)O)CCC4=C3C=CC(=C4)OC5CCCC5
InChI
  • InChI=1S/C25H32O3/c1-3-25(27)23(26)15-22-21-10-8-16-14-18(28-17-6-4-5-7-17)9-11-19(16)20(21)12-13-24(22,25)2/h1,9,11,14,17,20-23,26-27H,4-8,10,12-13,15H2,2H3/t20-,21-,22+,23-,24+,25+/m1/s1
  • Key:CHZJRGNDJLJLAW-RIQJQHKOSA-N

See also

References
  1. Official Gazette of the United States Patent and Trademark Office: Patents. U.S. Department of Commerce, Patent and Trademark Office. 1975. p. 1677.
  2. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 891–. ISBN 978-1-4757-2085-3.
  3. "Nilestriol". Drugs.com.
  4. McGuire W (14 December 2013). Experimental Biology. Springer Science & Business Media. pp. 161–. ISBN 978-1-4757-4673-0.
  5. Schoenberg DR (1977). Biochemical Properties of the Cytoplasmic Estrogen Receptors from Immature Rat and Mature Rabbit Uteri (Ph.D. thesis). University of Wisconsin. p. A-17.
  6. "Section 10: Obstetrics and gynecology". Excerpta Medica. 1978.
  7. Aronson JK (21 February 2009). Meyler's Side Effects of Endocrine and Metabolic Drugs. Elsevier. pp. 173–. ISBN 978-0-08-093292-7.



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