8,9-Dehydroestradiol - Misplaced Pages

(Redirected from 8,9-dehydro-17β-estradiol) Chemical compound Pharmaceutical compound

8,9-Dehydroestradiol
Clinical data

Other names	Δ-Estradiol; Δ-17β-Estradiol; Estra-1,3,5(10),8-tetraen-17β-ol-3-one
Routes of administration	By mouth
Drug class	Estrogen
Identifiers
IUPAC name (13S,14S,17S)-13-methyl-6,7,11,12,14,15,16,17-octahydrocyclopentaphenanthrene-3,17-diol
CAS Number	23392-54-3
ChemSpider	8014038
Chemical and physical data
Formula	C₁₈H₂₂O₂
Molar mass	270.372 g·mol
3D model (JSmol)	Interactive image
SMILES Oc4cc3c(/C1=C(/2CC(O)2(CC1)C)CC3)cc4
InChI InChI=InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,16-17,19-20H,2,4,6-9H2,1H3/t16-,17-,18-/m0/s1 Key:UWYDUSMQFLTKBQ-BZSNNMDCSA-N

8,9-Dehydroestradiol, or Δ-17β-estradiol, also known as estra-1,3,5(10),8-tetraen-17β-ol-3-one, is a naturally occurring steroidal estrogen found in horses which is closely related to equilin, equilenin, and estradiol, and, as the 3-sulfate ester sodium salt, is a minor constituent of conjugated estrogens (Premarin). It is also an important active metabolite of 8,9-dehydroestrone, analogously to conversion of estrone or estrone sulfate into estradiol.

References

Fritz MA, Speroff L (28 March 2012). Clinical Gynecologic Endocrinology and Infertility. Lippincott Williams & Wilkins. pp. 751–. ISBN 978-1-4511-4847-3.
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.
Bhavnani BR, Nisker JA, Martin J, Aletebi F, Watson L, Milne JK (2000). "Comparison of pharmacokinetics of a conjugated equine estrogen preparation (premarin) and a synthetic mixture of estrogens (C.E.S.) in postmenopausal women". Journal of the Society for Gynecologic Investigation. 7 (3): 175–183. doi:10.1016/s1071-5576(00)00049-6. PMID 10865186.

ERTooltip Estrogen receptor agonists

Antiandrogens (e.g., bicalutamide)
GnRH agonists (e.g., GnRH (gonadorelin), leuprorelin)
Gonadotropins (e.g., FSHTooltip follicle-stimulating hormone, LHTooltip luteinizing hormone)

ERTooltip Estrogen receptor antagonists (incl. SERMsTooltip selective estrogen receptor modulators/SERDsTooltip selective estrogen receptor downregulators)	Acolbifene Anordrin Bazedoxifene Broparestrol Clomifene Cyclofenil Enclomifene Epitiostanol Lasofoxifene Mepitiostane Ormeloxifene Ospemifene Raloxifene Tamoxifen Toremifene Exclusively antagonistic: Elacestrant Fulvestrant Noncompetitive inhibitors: Trilostane
Aromatase inhibitors	First-generation: Aminoglutethimide Testolactone Second-generation: Fadrozole Formestane Third-generation: Anastrozole Exemestane Letrozole
Antigonadotropins	Androgens/anabolic steroids (e.g., testosterone, testosterone esters, nandrolone esters, oxandrolone, fluoxymesterone) D₂ receptor antagonists (prolactin releasers) (e.g., domperidone, metoclopramide, risperidone, haloperidol, chlorpromazine, sulpiride) GnRH agonists (e.g., leuprorelin, goserelin) GnRH antagonists (e.g., cetrorelix, elagolix) Progestogens (e.g., chlormadinone acetate, cyproterone acetate, gestonorone caproate, hydroxyprogesterone caproate, medroxyprogesterone acetate, megestrol acetate)
Others	Mixed mechanism of action: Danazol Gestrinone Androstenedione immunogens: Androvax (androstenedione albumin) Ovandrotone albumin (Fecundin)

See also: Estrogen receptor modulators; Androgens and antiandrogens; Progestogens and antiprogestogens; List of estrogens

ERTooltip Estrogen receptor

Agonists

Mixed
(SERMsTooltip Selective estrogen receptor modulators)

Antagonists

GPERTooltip G protein-coupled estrogen receptor

Agonists	2-Methoxyestradiol 7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Aldosterone Atrazine Bisphenol A Daidzein DDT (p,p'-DDT, o',p'-DDE) Diarylpropionitrile Equol Estradiol Ethinylestradiol Fulvestrant (ICI-182780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Niacin Niacinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol STX Tamoxifen Tectoridin
Antagonists	CCL18 Estriol G-15 G-36 MIBE
Unknown	Diethylstilbestrol Zearalenone

See also: Receptor/signaling modulators; Estrogens and antiestrogens; Androgen receptor modulators; Progesterone receptor modulators; List of estrogens

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