From Wikipedia, the free encyclopedia
8,9-Dehydroestrone Other names Δ8 -Estrone; Estra-1,3,5(10),8-tetraen-3-ol-17-one Routes of By mouth Drug class Estrogen
(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 ) Formula C 18 H 20 O 2 Molar mass 268.350 g/mol 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] 8,9-dehydro-17β-estradiol as an important active metabolite , analogously to conversion of estrone or estrone sulfate into estradiol .[ 2] [ 4] [ 5] [ 3] [ 6] [ 3] 8,9-dehydro-17α-estradiol is likely also to be present in conjugated estrogens, but has not been identified at this time.[ 2]
Composition of conjugated estrogens and properties of constituents
Compound
Synonym
Proportion (%)
Relative potency vagina (%)
Relative potencyuterus (%)
RBA Tooltip Relative binding affinity forERα (%)RBA forERβ (%)ERα / ERβRBA ratio
Conjugated estrogens
–
100
38
100
–
–
–
Estrone –
49.1–61.5
30
32
26
52
0.50
Equilin Δ7 -Estrone
22.4–30.5
42
80
13
49
0.26
17α-Dihydroequilin Δ7 -17α-Estradiol
13.5–19.5
0.06
2.6
41
32
1.30
17α-Estradiol –
2.5–9.5
0.11
3.5
19
42
0.45
Δ8 -Estrone
–
3.5–3.9
?
?
19
32
0.60
Equilenin Δ6,8 -Estrone
2.2–2.8
1.3
11.4
15
20–29
0.50–0.75
17β-Dihydroequilin Δ7 -17β-Estradiol
0.5–4.0
83
200
113
108
1.05
17α-Dihydroequilenin Δ6,8 -17α-Estradiol
1.2–1.6
0.018
1.3
20
49
0.40
17β-Estradiol –
0.56–0.9
100
?
100
100
1.00
17β-Dihydroequilenin Δ6,8 -17β-Estradiol
0.5–0.7
0.21
9.4
68
90
0.75
Δ8 -17β-Estradiol –
Small amounts
?
?
68
72
0.94
Notes: All listed compounds are present in conjugated estrogen products specifically in the form of the sodium salts of the sulfate esters (i.e., as sodium estrone sulfate, sodium equilin sulfate, etc.). Sources: See template.
See also
References
^ Marc A. Fritz; Leon Speroff (28 March 2012). Clinical Gynecologic Endocrinology and Infertility ISBN 978-1-4511-4847-3 ^ a b c 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 . ^ 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". J. Steroid Biochem. Mol. Biol . 67 (2): 119–31. doi :10.1016/s0960-0760(98)00082-x . PMID 9877212 . ^ 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" . J. Clin. Endocrinol. Metab . 84 (6): 2020–7. doi :10.1210/jcem.84.6.5800 PMID 10372704 . ^ 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 . ^ 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.
Estrogens
ER Tooltip Estrogen receptor agonists
Steroidal: Alfatradiol Certain androgens /anabolic steroids (e.g., testosterone , testosterone esters , methyltestosterone , metandienone , nandrolone esters ) (via estrogenic metabolites)
Certain progestins (e.g., norethisterone , noretynodrel , etynodiol diacetate , tibolone )
Clomestrone Cloxestradiol acetate Conjugated estriol Conjugated estrogens Epiestriol Epimestrol Esterified estrogens Estetrol † Estradiol Estradiol esters (e.g., estradiol acetate , estradiol benzoate , estradiol cypionate , estradiol enanthate , estradiol undecylate , estradiol valerate , polyestradiol phosphate , estradiol ester mixtures (Climacteron ))Estramustine phosphate Estriol Estriol esters (e.g., estriol succinate , polyestriol phosphate )Estrogenic substances Estrone Estrone esters
Ethinylestradiol #
Hydroxyestrone diacetate Mestranol Methylestradiol Moxestrol Nilestriol Prasterone (dehydroepiandrosterone; DHEA)
Promestriene Quinestradol Quinestrol Progonadotropins
Antiestrogens
ER Tooltip Estrogen receptor antagonistsSERMs Tooltip selective estrogen receptor modulators /SERDs Tooltip selective estrogen receptor downregulators )Aromatase inhibitors 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 agonistsleuprorelin , goserelin )GnRH antagonistscetrorelix , elagolix )Progestogens (e.g., chlormadinone acetate , cyproterone acetate , gestonorone caproate , hydroxyprogesterone caproate , medroxyprogesterone acetate , megestrol acetate ) Others
ER Tooltip Estrogen receptor
Agonists
Steroidal: 2-Hydroxyestradiol 2-Hydroxyestrone 3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol 3α-Androstanediol 3α,5α-Dihydrolevonorgestrel 3β,5α-Dihydrolevonorgestrel 3α-Hydroxytibolone 3β-Hydroxytibolone 3β-Androstanediol 4-Androstenediol 4-Androstenedione 4-Fluoroestradiol 4-Hydroxyestradiol 4-Hydroxyestrone 4-Methoxyestradiol 4-Methoxyestrone 5-Androstenediol 7-Oxo-DHEA 7α-Hydroxy-DHEA 7α-Methylestradiol 7β-Hydroxyepiandrosterone 8,9-Dehydroestradiol 8,9-Dehydroestrone 8β-VE2 10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED) 11β-Chloromethylestradiol 11β-Methoxyestradiol 15α-Hydroxyestradiol 16-Ketoestradiol 16-Ketoestrone 16α-Fluoroestradiol 16α-Hydroxy-DHEA 16α-Hydroxyestrone 16α-Iodoestradiol 16α-LE2 16β-Hydroxyestrone 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol) 17α-Estradiol (alfatradiol )17α-Dihydroequilenin 17α-Dihydroequilin 17α-Epiestriol (16α-hydroxy-17α-estradiol) 17α-Ethynyl-3α-androstanediol 17α-Ethynyl-3β-androstanediol 17β-Dihydroequilenin 17β-Dihydroequilin 17β-Methyl-17α-dihydroequilenin Abiraterone Abiraterone acetate 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
Conjugated estriol Conjugated estrogens Cyclodiol Cyclotriol DHEA DHEA-S ent -EstradiolEpiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol) Epimestrol Equilenin Equilin ERA-63 (ORG-37663) Esterified estrogens Estetrol Estradiol
Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol
Estrofurate Estrogenic substances Estromustine Estrone
Etamestrol (eptamestrol) Ethinylandrostenediol
Ethinylestradiol
Ethinylestriol Ethylestradiol Etynodiol Etynodiol diacetate Hexolame Hippulin Hydroxyestrone diacetate Lynestrenol Lynestrenol phenylpropionate Mestranol Methylestradiol Moxestrol Mytatrienediol Nilestriol Norethisterone Noretynodrel Orestrate Pentolame Prodiame Prolame Promestriene RU-16117 Quinestradol Quinestrol Tibolone 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 , HPTE , 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 , rhaponticin )Synthetic xenoestrogens (e.g., alkylphenols , bisphenols (e.g., BPA , BPF , BPS ), DDT , parabens , PBBs , PHBA , phthalates , PCBs )Others (e.g., agnuside , rotundifuran ) MixedSERMs Tooltip Selective estrogen receptor modulators ) Antagonists
Coregulator-binding modulators: ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Agonists Antagonists Unknown
