8,9-Dehydroestroneのソースを表示

{{Short description|Chemical compound}}
{{Infobox drug
| Verifiedfields = 
| Watchedfields = 
| verifiedrevid = 
| IUPAC_name = (13''S'',14''S'')-3-Hydroxy-13-methyl-7,11,12,14,15,16-hexahydro-6''H''-cyclopenta[''a'']phenanthren-17-one
| image = 8,9-Dehydroestrone.svg
| width = 225px

<!--Clinical data-->
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
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| routes_of_administration = [[Oral administration|By mouth]]
| class = [[Estrogen (medication)|Estrogen]]

<!--Pharmacokinetic data-->
| bioavailability = 
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<!-- Identifiers -->
| CAS_number_Ref = 
| CAS_number = 474-87-3
| CAS_supplemental = 
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| ATC_supplemental = 
| PubChem = 6451472
| IUPHAR_ligand = 
| DrugBank_Ref = 
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| ChemSpiderID_Ref = 
| ChemSpiderID = 4953937
| UNII = 7C1N8RKG9F
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| synonyms = Δ<sup>8</sup>-Estrone; Estra-1,3,5(10),8-tetraen-3-ol-17-one

<!--Chemical data-->
| C=18 | H=20 | O=2
| SMILES = C[C@]12CCC3=C([C@@H]1CCC2=O)CCC4=C3C=CC(=C4)O
| StdInChI_Ref = 
| StdInChI = 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
| StdInChIKey_Ref = 
| StdInChIKey = OUGSRCWSHMWPQE-WMZOPIPTSA-N
}}

'''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 ==
* [[List of estrogens#Equine estrogens|List of estrogens § Equine estrogens]]

== References ==
{{Reflist}}

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

{{DEFAULTSORT:Dehydroestrone, 8, 9-}}
[[Category:Hydroxyarenes]]
[[Category:Estranes]]
[[Category:Estrogens]]
[[Category:Ketones]]


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