Chemistry:Ethinylandrostenediol

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Short description: Chemical compound
Ethinylandrostenediol
Ethinylandrostenediol.svg
Clinical data
Other namesSKF-2856; 17α-Ethynyl-5-androstenediol; 17α-Ethynylandrost-5-ene-3β,17-diol; 17α-Pregn-5-en-20-yne-3β,17-diol; NSC-17098
Drug classEstrogen; Progestogen; Progestin
Identifiers
CAS Number
ChemSpider
ChEMBL
Chemical and physical data
FormulaC21H30O2
Molar mass314.469 g·mol−1
3D model (JSmol)

Ethinylandrostenediol (developmental code name SKF-2856), also known as 17α-ethynyl-5-androstenediol, is a synthetic estrogen, progestogen, and androgen which was never marketed.[1][2][3][4][5][6] It is the C17α ethynyl derivative of the androgen precursor and prohormone 5-androstenediol.[1]

Ethinylandrostenediol was first synthesized in the late 1930s and along with its close analogue ethisterone (17α-ethynyltestosterone) was one of the first progestins (synthetic progestogens) to be developed.[7][8][9] Ethinylandrostenediol is orally active similarly to ethisterone and shows about half its progestogenic potency.[9] Ethinylandrostenediol was an intermediate in the initial synthesis of ethisterone.[10]

Ethinylandrostenediol shows tissue selectivity in its estrogenic effects in animals and doesn't seem to have estrogenic effects in the uterus.[1] The androgenic activity of ethinylandrostenediol is weak.[9]

An ester of ethinylandrostenediol, ethandrostate (17α-ethynyl-5-androstenediol 3β-cyclohexylpropionate), has been studied clinically in men and women with prostate cancer and breast cancer, respectively.[11][12][13][14][15]

Notable structural analogues of ethinylandrostenediol include 5-androstenediol, 17α-ethynyl-3β-androstanediol, 17α-ethynyl-3α-androstanediol, ethisterone (17α-ethynyltestosterone), and methandriol (17α-methyl-5-androstenediol), as well as ethinylestradiol (17α-ethynylestradiol or 17α-ethynylestra-1,3,5(10)-triene-3,17β-diol).


References

  1. ↑ 1.0 1.1 1.2 Tan VY (2010). Characterization of the estrogenic activity of a synthetic adrenal steroid 17-α ethinyl androstenediol and its potential use in hormone replacement therapy (Ph.D. thesis). hdl:10356/45321.
  2. ↑ "Uterine growth stimulating and testicular growth suppressing activities of 17alpha-ethinylandrostane-3beta, 17beta-diol, its delta 5-analog and derivatives". Proc. Soc. Exp. Biol. Med. 92 (2): 404–8. June 1956. doi:10.3181/00379727-92-22493. PMID 13350363. 
  3. ↑ "Additional steroids with luteoid activity.". Journal of Pharmacology and Experimental Therapeutics 84 (1): 46–52. 1945. 
  4. ↑ "Luteoid activity of ethinyl-androstenediol". Acta Brevia Neerl Physiol Pharmacol Microbiol e A 15 (5–7): 68. 1948. PMID 18873577. 
  5. ↑ "The antiluteinizing potency of five derivatives of progesterone". Endocrinology 58 (2): 212–9. February 1956. doi:10.1210/endo-58-2-212. PMID 13285465. 
  6. ↑ "Chemische Konstitution und pharmakologische Wirkung". Die Gestagene. Handbuch der experimentellen Pharmakologie / Handbook of Experimental Pharmacology. Springer. 1968. pp. 680–1025. doi:10.1007/978-3-642-99941-3_6. ISBN 978-3-642-99942-0. 
  7. ↑ "Preparation of a Pregnane Compound from Dehydroandrosterone". Journal of the American Chemical Society 61 (1): 79–80. 1939. doi:10.1021/ja01870a023. ISSN 0002-7863. 
  8. ↑ "The Preparation of Δ5-Pregnenediol-3,17-one-20 from Δ5-17-Ethynyl-androstenediol-3,17". Journal of the American Chemical Society 62 (3): 489–491. 1940. doi:10.1021/ja01860a007. ISSN 0002-7863. 
  9. ↑ 9.0 9.1 9.2 Hormone Assay. Elsevier Science. 22 October 2013. pp. 422–. ISBN 978-1-4832-7286-3. https://books.google.com/books?id=cCzgBAAAQBAJ&pg=PA422. 
  10. ↑ Drug Discovery: A History. John Wiley & Sons. 23 June 2005. pp. 200–. ISBN 978-0-471-89979-2. https://books.google.com/books?id=Cb6BOkj9fK4C&pg=PA200. 
  11. ↑ "17α-alkynyl 3α, 17β-androstanediol non-clinical and clinical pharmacology, pharmacokinetics and metabolism". Invest New Drugs 30 (1): 59–78. February 2012. doi:10.1007/s10637-010-9517-0. PMID 20814732. 
  12. ↑ "Anti-gonadotropic steroids, inhibition of ovulation and mating". Bioassay. Elsevier. 1962. pp. 179–274. ISBN 978-1-4832-7276-4. https://books.google.com/books?id=WS_LBAAAQBAJ&pg=PA179. 
  13. ↑ "Effects of ethandrostate on pituitary and sex organs of rats". Anatomical Record 124 (2): 260. January 1956. 
  14. ↑ "Esters of 17α-Ethinyl-androstane-3β,17β-diol and 17 α-Ethinylandrost-5-ene-3β, 17β-diol". The Journal of Organic Chemistry 22 (4): 473–475. 1957. doi:10.1021/jo01355a627. ISSN 0022-3263. 
  15. ↑ "Ethandrostate: endocrine effects and studies in treatment of cancer". Cancer 11 (3): 537–45. 1958. doi:10.1002/1097-0142(195805/06)11:3<537::aid-cncr2820110313>3.0.co;2-w. PMID 13523561. 





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