8,9-Dehydroestradiol

8,9-Dehydroestradiol
Clinical data

Routes of administration	Oral
Identifiers
IUPAC name (13S,14S,17S)-13-Methyl-6,7,11,12,14,15,16,17-octahydrocyclopenta[a]phenanthrene-3,17-diol
CAS Number	23392-54-3
ChemSpider	8014038
Chemical and physical data
Formula	C₁₈H₂₂O₂
Molar mass	270.3661 g/mol
3D model (JSmol)	Interactive image
SMILES Oc4cc3c(/C1=C(/[C@@H]2CC[C@H](O)[C@]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 Δ⁸-estradiol, also known as estra-1,3,5(10),8-tetraen-17β-ol-3-one, is a naturally occurring steroidal estrogen found in horses that is closely related to equilin, equilenin, and estradiol, and, as the 3-sulfate ester sodium salt, is a minor constituent of conjugated equine estrogens (Premarin).^[1] It is also an important active metabolite of 8,9-dehydroestrone, analogously to conversion of estrone or estrone sulfate into estradiol.^[2]^[3]

References

↑ Marc A. Fritz; Leon Speroff (28 March 2012). Clinical Gynecologic Endocrinology and Infertility. Lippincott Williams & Wilkins. pp. 751–. ISBN 978-1-4511-4847-3.
↑ Kuhl H (2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 Suppl 1: 3–63. PMID 16112947. doi:10.1080/13697130500148875.
↑ 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". J. Soc. Gynecol. Investig. 7 (3): 175–83. PMID 10865186. doi:10.1016/s1071-5576(00)00049-6.

Estrogens and antiestrogens

Estrogens

ER agonists

Steroidal: Alfatradiol
Certain androgens/anabolic steroids (e.g., testosterone, testosterone esters, nandrolone esters, methyltestosterone, metandienone) (via estrogenic metabolites)
Certain progestins (e.g., norethisterone, noretynodrel, etynodiol diacetate, tibolone)
Clomestrone
Cloxestradiol acetate
Conjugated equine estrogens/esterified estrogens (Premarin)
Epiestriol
Epimestrol
Estetrol^†
Estradiol
- Estradiol esters
- Polyestradiol phosphate
Estramustine phosphate
Estriol
- Emmenin
- Estriol esters
- Progynon
Estrone
- Estrone esters
- Estropipate (piperazine estrone sulfate)
Ethinylestradiol^#
- Ethinylestradiol sulfonate
Hydroxyestrone diacetate
Mestranol
Methylestradiol
Moxestrol
Nilestriol
Promestriene
Quinestradol
Quinestrol

Progonadotropins

Antiandrogens (e.g., bicalutamide)
GnRH agonists (e.g., GnRH (gonadorelin), leuprorelin)
Gonadotropins (e.g., FSH, LH)

Antiestrogens

ER antagonists (incl. SERMs/SERDs)	Acolbifene^† Anordrin Bazedoxifene (+conjugated equine estrogens) Broparestrol Clomifene^# Cyclofenil Enclomifene^† Epitiostanol Lasofoxifene Mepitiostane Ormeloxifene Ospemifene Spironolactone Raloxifene Tamoxifen^# Toremifene Exclusively antagonistic: Fulvestrant
Aromatase inhibitors	Non-selective: Aminoglutethimide Testolactone Selective: Anastrozole Exemestane Fadrozole Formestane 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) 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)

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

See also: Androgens and antiandrogens • Progestogens and antiprogestogens • Glucocorticoids and antiglucocorticoids • Mineralocorticoids and antimineralocorticoids • Gonadotropins and GnRH

Estrogen receptor modulators

Agonists	Steroidal: 2-Hydroxyestradiol 2-Hydroxyestrone 3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol 3α-Androstanediol 3β-Androstanediol 4-Androstenediol 4-Androstenedione 4-Hydroxyestradiol 4-Hydroxyestrone 4-Methoxyestradiol 4-Methoxyestrone 5-Androstenediol 7-Oxo-DHEA 7α-Hydroxy-DHEA 7β-Hydroxyepiandrosterone 8,9-Dehydroestradiol 8,9-Dehydroestrone 8β-VE2 10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED) 16α-Hydroxy-DHEA 16α-Hydroxyestrone 16α-Iodo-E2 16α-LE2 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol) 17α-Dihydroequilenin 17α-Dihydroequilin 17α-Epiestriol (16α-hydroxy-17α-estradiol) 17β-Dihydroequilenin 17β-Dihydroequilin Abiraterone Abiraterone acetate 17α-Estradiol (alfatradiol) Alestramustine Almestrone Anabolic steroids (e.g., testosterone and esters, methyltestosterone, metandienone (methandrostenolone), nandrolone and esters, many others; via estrogenic metabolites) Atrimustine Bolandiol Bolandiol dipropionate Butolame Clomestrone Cloxestradiol Cloxestradiol acetate DHEA DHEA-S Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol) Epimestrol Equilenin Equilin ERA-63 (ORG-37663) Estetrol Estradiol Estradiol esters Lipoidal estradiol Polyestradiol phosphate Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol Estriol esters Estrofurate Estromustine Estrone Estrone esters Estropipate Etamestrol (eptamestrol) Ethinylestradiol Ethinylestradiol sulfonate Ethinylestriol Etynodiol diacetate Hexolame Hippulin Hydroxyestrone diacetate Mestranol Methylestradiol Moxestrol Mytatrienediol Nilestriol Noretynodrel Orestrate Pentolame Prodiame Prolame Promestriene Quinestradol Quinestrol Nonsteroidal: (R,R)-THC (S,S)-THC 2,8-DHHHC AC-186 Allenestrol Allenolic acid Benzestrol Bifluranol Bisdehydrodoisynolic acid Carbestrol D-15414 DCW234 Diarylpropionitrile Dienestrol Dienestrol diacetate Diethylstilbestrol Diethylstilbestrol esters Dimestrol (dianisylhexene) Doisynoestrol (fenocycline) Doisynolic acid Efavirenz ERB-196 (WAY-202196) Erteberel (SERBA-1, LY-500307) Estrobin (DBE) Fenestrel FERb 033 Fosfestrol (diethylstilbestrol diphosphate) Furostilbestrol (diethylstilbestrol difuroate) GTx-758 Hexestrol Hexestrol esters ICI-85966 (Stilbostat) Mestilbol Methallenestril Methestrol Methestrol dipropionate Paroxypropione Pentafluranol Phenestrol Prinaberel (ERB-041, WAY-202041) Propylpyrazoletriol Quadrosilan SC-4289 SERBA-2 SKF-82,958 Terfluranol Triphenylbromoethylene Triphenylchloroethylene Triphenyliodoethylene Triphenylmethylethylene (triphenylpropene) WAY-166818 WAY-200070 WAY-214156 Unknown/unsorted: ERB-26 ERA-45 ERB-79 Xenoestrogens: Anise-related (e.g., anethole, anol, dianethole, dianol, photoanethole) Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone) Coumestans (e.g., coumestrol, psoralidin) Flavonoids (incl. 7,8-DHF, 8-prenylnaringenin, apigenin, baicalein, baicalin, biochanin A, calycosin, catechin, daidzein, daidzin, ECG, EGCG, epicatechin, equol, formononetin, glabrene, glabridin, genistein, genistin, glycitein, kaempferol, liquiritigenin, mirificin, myricetin, naringenin, penduletin, pinocembrin, prunetin, puerarin, quercetin, tectoridin, tectorigenin) Lavender oil Lignans (e.g., enterodiol, enterolactone, nyasol (cis-hinokiresinol)) Metalloestrogens (e.g., cadmium) Pesticides (e.g., alternariol, dieldrin, endosulfan, fenarimol, methiocarb, methoxychlor, triclocarban, triclosan) Phytosteroids (e.g., digitoxin (digitalis), diosgenin, guggulsterone) Phytosterols (e.g., β-sitosterol, campesterol, stigmasterol) Resorcylic acid lactones (e.g., zearalanone, α-zearalenol, β-zearalenol, zearalenone, zeranol (α-zearalanol), taleranol (teranol, β-zearalanol)) Steroid-like (e.g., deoxymiroestrol, miroestrol) Stilbenoids (e.g., resveratrol) Synthetic xenoestrogens (e.g., alkylphenols, bisphenols (e.g., BPA, BPF, BPS), DDT, parabens, PBBs, PHBA, phthalates, PCBs) Others (e.g., agnuside, rotundifuran)
Mixed (SERMs)	2-Phenylbenzofuran 2-Phenylbenzothiophene 4'-Hydroxynorendoxifen 27-Hydroxycholesterol Acefluranol Acolbifene Afimoxifene Anordiol Anordrin Arzoxifene Bazedoxifene Brilanestrant Broparestrol Elacestrant Chlorotrianisene Clomifene Clomifenoxide Cyclofenil D-15413 Droloxifene Enclomifene Endoxifen Etacstil (GW-5638, DPC-974) Ethamoxytriphetol (MER-25) Femarelle Fispemifene GW-7604 ICI-55548 Idoxifene Lasofoxifene Levormeloxifene LN-1643 LN-2299 LY-117018 Menerba Miproxifene Miproxifene phosphate Nafoxidine Nitromifene Ormeloxifene Ospemifene Panomifene Pipendoxifene Raloxifene Spironolactone SS1010 Tamoxifen TAS-108 (SR-16234) Tibolone Toremifene Trioxifene TZE-5323 Y-134 Zindoxifene Zuclomifene
Antagonists	(R,R)-THC 7β-Hydroxy-DHEA Chloroindazole Cytestrol acetate Epitiostanol ERA-90 ERB-88 Fulvestrant (ICI-182780) Glyceollins (I, II, III, IV) ICI-164384 Mepitiostane Methylepitiostanol Methylpiperidinopyrazole MIBE Oxabicycloheptene sulfonate Phenytoin PHTPP Prochloraz RU-58668 SS1020 TAS-108 (SR-16234) ZB716 ZK-164015 ZK-191703

GPER

Agonists

Antagonists

CCL18
Estriol
G-15
G-36
MIBE

See also: Receptor/signaling modulators; Androgenics; Glucocorticoidics; Mineralocorticoidics; Progestogenics; Steroid metabolism modulators; List of estrogens

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.