Doisynolic acid

Doisynolic acid

Systematic (IUPAC) name
1-Ethyl-7-hydroxy-2-methyl-3,4,4a,9,10,10a-hexahydro-1H-phenanthrene-2-carboxylic acid
Identifiers
CAS Number	482-49-5
ATC code	None
PubChem	CID: 101706
ChemSpider	91894
Chemical data
Formula	C18H24O3
Molecular mass	288.38136 g/mol
SMILES CCC1C2CCC3=C(C2CCC1(C)C(=O)O)C=CC(=C3)O
InChI InChI=1S/C18H24O3/c1-3-16-15-6-4-11-10-12(19)5-7-13(11)14(15)8-9-18(16,2)17(20)21/h5,7,10,14-16,19H,3-4,6,8-9H2,1-2H3,(H,20,21) Key:GEGYYIFBFKSCPK-UHFFFAOYSA-N

Doisynolic acid is a synthetic, non-steroidal, orally active estrogen that was never marketed. The reaction of estradiol or estrone with potassium hydroxide, a strong base, results in doisynolic acid as a degradation product, which retains high estrogenic activity, and this reaction was how the drug was discovered, in the late 1930s. The drug is a highly active and potent estrogen by the oral or subcutaneous route. The reaction of equilenin or dihydroequilenin with potassium hydroxide was also found to produce bisdehydrodoisynolic acid, the levorotatory isomer of which is an estrogen with an "astonishingly" high degree of potency, while the dextrorotatory isomer is inactive.

Doisynolic acid is the parent compound of a group of synthetic, non-steroidal estrogens with high oral activity. The synthetic, non-steroidal estrogens methallenestril, fenestrel, and carbestrol were all derived from doisynolic acid and are seco analogues of the compound. Doisynoestrol, also known as fenocycline, is cis-bisdehydrdoisynolic acid methyl ether, and is another estrogenic derivative.

See also

• Diethylstilbestrol
• Stilbestrol
• Chlorotrianisene
• Triphenylethylene