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Chemical compound
Doisynolic acid
ATC code
1-Ethyl-7-hydroxy-2-methyl-3,4,4a,9,10,10a-hexahydro-1H-phenanthrene-2-carboxylic acid
CAS Number
PubChem
CID
ChemSpider
UNII
CompTox Dashboard (
EPA )
Formula C 18 H 24 O 3
Molar mass 288.387 g·mol−1 3D model (
JSmol )
CCC1C2CCC3=C(C2CCC1(C)C(=O)O)C=CC(=C3)O
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 ,
orally active ,
nonsteroidal estrogen that was never marketed.
[1]
[2]
[3] 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.
[4]
[5]
[6] The drug is a highly active and potent estrogen by the oral or subcutaneous route.
[4] The reaction of
equilenin or
dihydroequilenin with potassium hydroxide was also found to produce
bisdehydrodoisynolic acid , whose levorotatory isomer is an estrogen with an "astonishingly" high degree of potency, while the dextrorotatory isomer is inactive.
[4] Doisynolic acid was named after
Edward Adelbert Doisy , a pioneer in the field of estrogen research and one of the discoverers of estrone.
[7]
Doisynolic acid is the parent compound of a group of synthetic, nonsteroidal estrogens with high oral activity.
[8] The synthetic, nonsteroidal estrogens
methallenestril ,
fenestrel , and
carbestrol were all derived from doisynolic acid and are seco-
analogues of the compound.
[9]
Doisynoestrol , also known as fenocycline, is cis -bisdehydrdoisynolic acid methyl ether, and is another estrogenic derivative.
[10]
See also
References
^ Hill RA, Makin HL, Kirk DN, Murphy GM (23 May 1991).
Dictionary of Steroids . CRC Press. pp. 422–.
ISBN
978-0-412-27060-4 .
^ Leclerc G (2 December 2012).
"Estrogens, Antiestrogens, and Other Estrane Compounds" . In Blickenstaff RT (ed.). Antitumor Steroids . Academic Press. pp. 11–12.
ISBN
978-0-323-13916-8 .
^ Hilf R, Wittliff JL (27 November 2013).
"Mechanims of Action of Estrogens" . In Sartorelli AC, Johns DG (eds.). Antineoplastic and Immunosuppressive Agents . Springer Science & Business Media. pp. 106–.
ISBN
978-3-642-65806-8 .
^
a
b
c Pearlman WH (2 December 2012).
"The Chemistry and Metabolism of the Estrogens" . In Pincus G, Thimann KV (eds.). The Hormones V1: Physiology, Chemistry and Applications . Elsevier. pp. 364–366.
ISBN
978-0-323-14206-9 .
^ Blickenstaff RT, Ghosh AC, Wolf GC (22 October 2013).
"Chapter 3.4: 18,19-Norprogesterone and 19-Norpreganes" . Total Synthesis of Steroids: Organic Chemistry: A Series of Monographs . Elsevier Science. pp. 65–.
ISBN
978-1-4832-1642-3 .
^ Brueggemeir RW, Miller DD, Dalton JT (January 2002).
"Estrogen, Progestins, and Androgens" . In Williams DA, Foye WO, Lemke TL (eds.). Foye's Principles of Medicinal Chemistry . Lippincott Williams & Wilkins. pp. 692–.
ISBN
978-0-683-30737-5 .
^ Dodds C (May 1955).
"Synthetic oestrogens" . British Medical Bulletin . 11 (2): 131–134.
doi :
10.1093/oxfordjournals.bmb.a069465 .
PMID
14378564 .
^ Frieden E (2 December 2012).
"Estrogens" . Chemical Endocrinology . Elsevier Science. pp. 53–.
ISBN
978-0-323-15906-7 .
^ Kirk RE, Othmer DF (1980).
Encyclopedia of chemical technology . Wiley. p. 670,672.
ISBN
978-0-471-02065-3 .
^ 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 .
ER Tooltip Estrogen receptor
Agonists
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3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
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17α-Ethynyl-3α-androstanediol
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Agonists Antagonists Unknown