From Wikipedia, the free encyclopedia
Chemical compound
8,9-Dehydroestrone
Other names Δ8 -Estrone; Estra-1,3,5(10),8-tetraen-3-ol-17-one
Routes of administration
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 268.356 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
References
^ 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 .
^
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 .
^
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 .
^
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 .
^ 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, 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.
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 antagonists (incl.
SERMs 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 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
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 -Estradiol
Epiestriol (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 )
Mixed (
SERMs Tooltip Selective estrogen receptor modulators ) Antagonists
Coregulator-binding modulators:
ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Agonists Antagonists Unknown