Chemistry:8,9-Dehydroestrone

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Short description: Chemical compound
8,9-Dehydroestrone
8,9-Dehydroestrone.svg
Clinical data
Other namesΔ8-Estrone; Estra-1,3,5(10),8-tetraen-3-ol-17-one
Routes of
administration
By mouth
Drug classEstrogen
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC18H20O2
Molar mass268.356 g·mol−1
3D model (JSmol)

8,9-Dehydroestrone, or Δ8-estrone, also known as estra-1,3,5(10),8-tetraen-3-ol-17-one, is a naturally occurring estrogen found in horses which is closely related to equilin, equilenin, and estrone, and, as the 3-sulfate ester sodium salt, is a minor constituent (3.5%) of conjugated estrogens (Premarin).[1][2][3][4] It produces 8,9-dehydro-17β-estradiol as an important active metabolite, analogously to conversion of estrone or estrone sulfate into estradiol.[2][4][5][3] The compound was first described in 1997.[6][3] In addition to 8,9-dehydroestrone and 8,9-dehydro-17β-estradiol, 8,9-dehydro-17α-estradiol is likely also to be present in conjugated estrogens, but has not been identified at this time.[2]

See also

References

  1. "Postmenopausal Hormone Therapy". Clinical Gynecologic Endocrinology and Infertility. Lippincott Williams & Wilkins. 28 March 2012. pp. 751–. ISBN 978-1-4511-4847-3. https://books.google.com/books?id=KZLubBxJEwEC&pg=PA751. 
  2. 2.0 2.1 2.2 "Pharmacokinetics and pharmacodynamics of conjugated equine estrogens: chemistry and metabolism". Proceedings of the Society for Experimental Biology and Medicine 217 (1): 6–16. January 1998. doi:10.3181/00379727-217-44199. PMID 9421201. 
  3. 3.0 3.1 3.2 "Pharmacokinetics and pharmacodynamics of a novel estrogen delta8-estrone in postmenopausal women and men". The Journal of Steroid Biochemistry and Molecular Biology 67 (2): 119–131. October 1998. doi:10.1016/s0960-0760(98)00082-x. PMID 9877212. 
  4. 4.0 4.1 "Estrogen activity and novel tissue selectivity of delta8,9-dehydroestrone sulfate in postmenopausal women". The Journal of Clinical Endocrinology and Metabolism 84 (6): 2020–2027. June 1999. doi:10.1210/jcem.84.6.5800. PMID 10372704. 
  5. "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric 8 (Suppl 1): 3–63. August 2005. doi:10.1080/13697130500148875. PMID 16112947. 
  6. "Effects in postmenopausal women of delta-8-estrone sulfate: A novel estrogen component of Premarin.". Journal Society Gynecologic Investigation 4 (1 (Suppl): 392. 1997.