8,9-Dehydroestrone

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]

8,9-Dehydroestrone
Clinical data
Other namesΔ8-Estrone; Estra-1,3,5(10),8-tetraen-3-ol-17-one
Routes of
administration		By mouth
Drug classEstrogen
Identifiers
IUPAC name
  • (13S,14S)-3-Hydroxy-13-methyl-7,11,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-17-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H20O2
Molar mass268.356 g·mol−1
3D model (JSmol)
SMILES
  • C[C@]12CCC3=C([C@@H]1CCC2=O)CCC4=C3C=CC(=C4)O
InChI
  • InChI=1S/C18H20O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,16,19H,2,4,6-9H2,1H3/t16-,18-/m0/s1
  • Key:OUGSRCWSHMWPQE-WMZOPIPTSA-N

See also

References
  1. Marc A. Fritz; Leon Speroff (28 March 2012). Clinical Gynecologic Endocrinology and Infertility. Lippincott Williams & Wilkins. pp. 751–. ISBN 978-1-4511-4847-3.
  2. Bhavnani BR (January 1998). "Pharmacokinetics and pharmacodynamics of conjugated equine estrogens: chemistry and metabolism". Proc. Soc. Exp. Biol. Med. 217 (1): 6–16. doi:10.3181/00379727-217-44199. PMID 9421201. S2CID 45177839.
  3. Bhavnani BR, Cecutti A, Gerulath A (October 1998). "Pharmacokinetics and pharmacodynamics of a novel estrogen delta8-estrone in postmenopausal women and men". J. Steroid Biochem. Mol. Biol. 67 (2): 119–31. doi:10.1016/s0960-0760(98)00082-x. PMID 9877212. S2CID 54352249.
  4. Baracat E, Haidar M, Lopez FJ, Pickar J, Dey M, Negro-Vilar A (June 1999). "Estrogen activity and novel tissue selectivity of delta8,9-dehydroestrone sulfate in postmenopausal women". J. Clin. Endocrinol. Metab. 84 (6): 2020–7. doi:10.1210/jcem.84.6.5800. PMID 10372704.
  5. Kuhl H (2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 Suppl 1: 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.
  6. Bhavnani B. R., Cecutti A. and Dey M. S., Effects in postmenopausal women of delta-8-estrone sulfate: A novel estrogen component of Premarin. Journal Society Gynecologic Investigation 4 (1 (Suppl.)) (1997) 392.



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