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{{Short description|Chemical compound}}
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<!--Chemical data-->
| C=18 | H=20 | O=2
| C=18 | H=20 | O=2
| molecular_weight = 268.350 g/mol
| SMILES = C[C@]12CCC3=C([C@@H]1CCC2=O)CCC4=C3C=CC(=C4)O
| SMILES = C[C@]12CCC3=C([C@@H]1CCC2=O)CCC4=C3C=CC(=C4)O
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'''8,9-Dehydroestrone''', or '''Δ<sup>8</sup>-estrone''', also known as '''estra-1,3,5(10),8-tetraen-3-ol-17-one''', is a [[naturally occurring]] [[estrogen (medication)|estrogen]] found in [[equine|horse]]s which is closely related to [[equilin]], [[equilenin]], and [[estrone]], and, as the 3-[[sulfate]] [[ester]] [[sodium]] [[salt (chemistry)|salt]], is a minor constituent (3.5%) of [[conjugated estrogens]] (Premarin).<ref name="FritzSperoff2012">{{cite book|author1=Marc A. Fritz|author2=Leon Speroff|title=Clinical Gynecologic Endocrinology and Infertility|url=https://books.google.com/books?id=KZLubBxJEwEC&pg=PA751|date=28 March 2012|publisher=Lippincott Williams & Wilkins|isbn=978-1-4511-4847-3|pages=751–}}</ref><ref name="pmid9421201">{{cite journal | vauthors = Bhavnani BR | title = Pharmacokinetics and pharmacodynamics of conjugated equine estrogens: chemistry and metabolism | journal = Proc. Soc. Exp. Biol. Med. | volume = 217 | issue = 1 | pages = 6–16 | date = January 1998 | pmid = 9421201 | doi = 10.3181/00379727-217-44199 | url = }}</ref><ref name="pmid9877212">{{cite journal | vauthors = Bhavnani BR, Cecutti A, Gerulath A | title = Pharmacokinetics and pharmacodynamics of a novel estrogen delta8-estrone in postmenopausal women and men | journal = J. Steroid Biochem. Mol. Biol. | volume = 67 | issue = 2 | pages = 119–31 | date = October 1998 | pmid = 9877212 | doi = | url = }}</ref> It produces [[8,9-dehydro-17β-estradiol]] as an important [[active metabolite]], analogously to conversion of estrone or [[estrone sulfate]] into [[estradiol (medication)|estradiol]].<ref name="pmid9421201" /><ref name="pmid16112947">{{cite journal | vauthors = Kuhl H | title = Pharmacology of estrogens and progestogens: influence of different routes of administration | journal = Climacteric | volume = 8 Suppl 1 | issue = | pages = 3–63 | year = 2005 | pmid = 16112947 | doi = 10.1080/13697130500148875 | url = }}</ref><ref name="pmid9877212" /> The compound was first described in 1997.<ref name="BhavnaniCecutti1997">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.</ref><ref name="pmid9877212" /> 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.<ref name="pmid9421201" />
'''8,9-Dehydroestrone''', or '''Δ<sup>8</sup>-estrone''', also known as '''estra-1,3,5(10),8-tetraen-3-ol-17-one''', is a [[naturally occurring]] [[estrogen (medication)|estrogen]] found in [[equine|horse]]s which is closely related to [[equilin]], [[equilenin]], and [[estrone]], and, as the 3-[[sulfate]] [[ester]] [[sodium]] [[salt (chemistry)|salt]], is a minor constituent (3.5%) of [[conjugated estrogens]] (Premarin).<ref name="FritzSperoff2012">{{cite book| vauthors = Fritz MA, Speroff L | chapter = Postmenopausal Hormone Therapy |title=Clinical Gynecologic Endocrinology and Infertility| chapter-url = https://books.google.com/books?id=KZLubBxJEwEC&pg=PA751 |date=28 March 2012|publisher=Lippincott Williams & Wilkins|isbn=978-1-4511-4847-3|pages=751–}}</ref><ref name="pmid9421201">{{cite journal | vauthors = Bhavnani BR | title = Pharmacokinetics and pharmacodynamics of conjugated equine estrogens: chemistry and metabolism | journal = Proceedings of the Society for Experimental Biology and Medicine | volume = 217 | issue = 1 | pages = 6–16 | date = January 1998 | pmid = 9421201 | doi = 10.3181/00379727-217-44199 | s2cid = 45177839 }}</ref><ref name="pmid9877212">{{cite journal | vauthors = Bhavnani BR, Cecutti A, Gerulath A | title = Pharmacokinetics and pharmacodynamics of a novel estrogen delta8-estrone in postmenopausal women and men | journal = The Journal of Steroid Biochemistry and Molecular Biology | volume = 67 | issue = 2 | pages = 119–131 | date = October 1998 | pmid = 9877212 | doi = 10.1016/s0960-0760(98)00082-x | s2cid = 54352249 }}</ref><ref name="pmid10372704">{{cite journal | vauthors = Baracat E, Haidar M, Lopez FJ, Pickar J, Dey M, Negro-Vilar A | title = Estrogen activity and novel tissue selectivity of delta8,9-dehydroestrone sulfate in postmenopausal women | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 84 | issue = 6 | pages = 2020–2027 | date = June 1999 | pmid = 10372704 | doi = 10.1210/jcem.84.6.5800 | doi-access = free }}</ref> It produces [[8,9-dehydro-17β-estradiol]] as an important [[active metabolite]], analogously to conversion of estrone or [[estrone sulfate]] into [[estradiol (medication)|estradiol]].<ref name="pmid9421201" /><ref name="pmid10372704" /><ref name="pmid16112947">{{cite journal | vauthors = Kuhl H | title = Pharmacology of estrogens and progestogens: influence of different routes of administration | journal = Climacteric | volume = 8 | issue = Suppl 1 | pages = 3–63 | date = August 2005 | pmid = 16112947 | doi = 10.1080/13697130500148875 | s2cid = 24616324 }}</ref><ref name="pmid9877212" /> The compound was first described in 1997.<ref name="BhavnaniCecutti1997">{{cite journal | vauthors = Bhavnani BR, Cecutti A, Dey MS | title = Effects in postmenopausal women of delta-8-estrone sulfate: A novel estrogen component of Premarin. | journal = Journal Society Gynecologic Investigation | date = 1997 | volume = 4 | issue = 1 (Suppl | pages = 392 }}</ref><ref name="pmid9877212" /> 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.<ref name="pmid9421201" />


==See also==
== See also ==
* [[List of estrogens#Equine estrogens|List of estrogens § Equine estrogens]]
* [[List of estrogens#Equine estrogens|List of estrogens § Equine estrogens]]


==References==
== References ==
{{Reflist}}
{{Reflist}}



{{Estrogens and antiestrogens}}
{{Estrogens and antiestrogens}}
{{Estrogen receptor modulators}}
{{Estrogen receptor modulators}}


{{DEFAULTSORT:Dehydroestrone, 8,9-}}
{{DEFAULTSORT:Dehydroestrone, 8, 9-}}
⚫
[[Category:Hydroxyarenes]]

⚫
[[Category:Alcohols]]
[[Category:Estranes]]
[[Category:Estranes]]
[[Category:Estrogens]]
[[Category:Estrogens]]

Latest revision as of 11:54, 21 October 2024

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
  • (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)
  • C[C@]12CCC3=C([C@@H]1CCC2=O)CCC4=C3C=CC(=C4)O
  • 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

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

[edit]

References

[edit]
  1. ^ Fritz MA, Speroff L (28 March 2012). "Postmenopausal Hormone Therapy". Clinical Gynecologic Endocrinology and Infertility. Lippincott Williams & Wilkins. pp. 751–. ISBN 978-1-4511-4847-3.
  2. ^ a b c Bhavnani BR (January 1998). "Pharmacokinetics and pharmacodynamics of conjugated equine estrogens: chemistry and metabolism". Proceedings of the Society for Experimental Biology and Medicine. 217 (1): 6–16. doi:10.3181/00379727-217-44199. PMID 9421201. S2CID 45177839.
  3. ^ a b c Bhavnani BR, Cecutti A, Gerulath A (October 1998). "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. doi:10.1016/s0960-0760(98)00082-x. PMID 9877212. S2CID 54352249.
  4. ^ a b 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". The Journal of Clinical Endocrinology and Metabolism. 84 (6): 2020–2027. doi:10.1210/jcem.84.6.5800. PMID 10372704.
  5. ^ Kuhl H (August 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 BR, Cecutti A, Dey MS (1997). "Effects in postmenopausal women of delta-8-estrone sulfate: A novel estrogen component of Premarin". Journal Society Gynecologic Investigation. 4 (1 (Suppl): 392.


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