From Wikipedia, the free encyclopedia
Chemical compound
Equilenin
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Other names | 6,8-Didehydroestrone; Estra-1,3,5(10),6,8-pentaen-3-ol-17-one |
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Routes of administration |
By mouth |
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Drug class |
Estrogen |
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(13S,14S)-3-hydroxy-13-methyl-12,14,15,16-tetrahydro-11H-cyclopenta[a]phenanthren-17-one
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CAS Number | |
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PubChem
CID | |
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DrugBank | |
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ChemSpider | |
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UNII | |
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KEGG | |
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ChEBI | |
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ChEMBL | |
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CompTox Dashboard (
EPA) | |
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ECHA InfoCard |
100.007.483
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Formula | C18H18O2 |
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Molar mass | 266.340 g·mol−1 |
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3D model (
JSmol) | |
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O=C4[C@]3(CCc1c(ccc2c1ccc(O)c2)[C@@H]3CC4)C
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InChI=1S/C18H18O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h2-5,10,16,19H,6-9H2,1H3/t16-,18-/m0/s1 YKey:PDRGHUMCVRDZLQ-WMZOPIPTSA-N Y
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Equilenin, also known as 6,8-didehydroestrone, as well as estra-1,3,5(10),6,8-pentaen-3-ol-17-one, is a
naturally occurring
steroidal
estrogen obtained from the
urine of
pregnant
mares.
[1]
[2] It is used as one of the components in
conjugated estrogens (brand name Premarin).
[2] It was the first complex natural product to be fully synthesized, in work reported by 1940 by
Bachmann and
Wilds.
[3]
Chemistry
Synthesis
Total synthesis
The synthesis developed by the
Bachmann group started from Butenand's ketone
[4] – the 7-methoxy
structural analog of
1,2,3,4-tetrahydrophenanthren-1-one
[5] – and which can be readily prepared from 1,6-
Cleve's acid.
[6] The approach was based on well-established transformations like the
Claisen condensation, the
Reformatsky reaction, the
Arndt–Eistert reaction, and the
Dieckmann condensation.
[3]
Nicolaou described this preparation as ending the era preceding the post-World War II work of
Robert Burns Woodward that introduced
enantioselective synthesis;
[4] in this synthesis, a mixture of stereoisomers were prepared and then
resolved,
[6] and the choice of target was partly because of the existence of only two chiral carbons and hence only four stereoisomers.
[5]
The overall yield of the synthesis was 2.7% based on a twenty-step process starting from Cleve's acid.
[6]
See also
References
-
^ Elks J (14 November 2014).
The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 494–.
ISBN
978-1-4757-2085-3.
- ^
a
b Fritz MA, Speroff L (28 March 2012).
Clinical Gynecologic Endocrinology and Infertility. Lippincott Williams & Wilkins. pp. 751–.
ISBN
978-1-4511-4847-3.
- ^
a
b
Bachmann WE, Cole W,
Wilds AL (1940). "The Total Synthesis of the Sex Hormone Equilenin and Its Stereoisomers".
J. Am. Chem. Soc. 62 (4): 824–839.
doi:
10.1021/ja01861a036.
- ^
a
b
Nicolaou KC, Vourloumis D, Winssinger N, Baran PS (January 2000).
"The Art and Science of Total Synthesis at the Dawn of the Twenty-First Century" (PDF). Angewandte Chemie. 39 (1): 44–122.
doi:
10.1002/(SICI)1521-3773(20000103)39:1<44::AID-ANIE44>3.0.CO;2-L.
PMID
10649349. Archived from
the original (PDF) on 2017-05-17. Retrieved 2017-07-22.
- ^
a
b
Bachmann WE, Cole W,
Wilds AL (1939). "The Total Synthesis of the Sex Hormone Equilenin".
J. Am. Chem. Soc. 61 (4): 974–975.
doi:
10.1021/ja01873a513.
- ^
a
b
c Nakanishi K (1974).
"Steroids". In Nakanishi K, Goto T, Itô S, Natori S, Nozoe S (eds.). Natural Products Chemistry. Vol. 1.
Academic Press. pp. 421–545.
ISBN
9781483218861.
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Estrogens |
ERTooltip 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
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Progonadotropins | |
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Antiestrogens |
ERTooltip Estrogen receptor antagonists (incl.
SERMsTooltip selective estrogen receptor modulators/
SERDsTooltip selective estrogen receptor downregulators) | |
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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)
|
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Others | |
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ERTooltip 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)
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17α-Estradiol (
alfatradiol)
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17α-Dihydroequilenin
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17α-Dihydroequilin
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17α-Epiestriol (16α-hydroxy-17α-estradiol)
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17α-Ethynyl-3α-androstanediol
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17α-Ethynyl-3β-androstanediol
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17β-Dihydroequilenin
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17β-Dihydroequilin
-
17β-Methyl-17α-dihydroequilenin
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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)
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Mixed (
SERMsTooltip Selective estrogen receptor modulators) | |
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Antagonists |
- Coregulator-binding modulators:
ERX-11
|
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GPERTooltip G protein-coupled estrogen receptor | Agonists | |
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Antagonists | |
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Unknown | |
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