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Chemical compound
Fispemifene
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Other names | HM-101 |
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2-(2-(4-((1Z)-4-Chloro-1,2-diphenylbut-1-enyl)phenoxy)ethoxy)ethanol
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CAS Number | |
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PubChem
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ChEMBL | |
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Formula | C26H27ClO3 |
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Molar mass | 422.95 g·mol−1 |
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3D model (
JSmol) | |
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C1=CC=C(C=C1)/C(=C(/C2=CC=CC=C2)\C3=CC=C(C=C3)OCCOCCO)/CCCl
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InChI=1S/C26H27ClO3/c27-16-15-25(21-7-3-1-4-8-21)26(22-9-5-2-6-10-22)23-11-13-24(14-12-23)30-20-19-29-18-17-28/h1-14,28H,15-20H2/b26-25- Key:NKZTZAQIKKGTDB-QPLCGJKRSA-N
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Fispemifene (
INN,
USAN) (developmental code name HM-101) is a
nonsteroidal
selective estrogen receptor modulator (SERM) of the
triphenylethylene group that was developed for the treatment of male
hypogonadism but was abandoned and never marketed.
[1]
[2]
[3] It reached
phase II
clinical trials for this indication before development was terminated in March 2016.
[1] The drug failed to achieve
statistical significance on key
effectiveness
endpoints in clinical trials and was discontinued by its developer for strategic reasons.
[1]
See also
References
External links
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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
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16α-Iodoestradiol
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16α-LE2
-
16β-Hydroxyestrone
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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
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Abiraterone
-
Abiraterone acetate
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Alestramustine
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Almestrone
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Anabolic steroids (e.g.,
testosterone and
esters,
methyltestosterone,
metandienone (methandrostenolone),
nandrolone and
esters, many others; via estrogenic metabolites)
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ERA-63 (ORG-37663)
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Etynodiol
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Etynodiol diacetate
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Hexolame
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Hippulin
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Hydroxyestrone diacetate
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Lynestrenol
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Lynestrenol phenylpropionate
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Mestranol
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Methylestradiol
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Moxestrol
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Nilestriol
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Norethisterone
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Orestrate
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Pentolame
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Prodiame
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RU-16117
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Quinestradol
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Quinestrol
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Tibolone
- Xenoestrogens:
Anise-related (e.g.,
anethole,
anol,
dianethole,
dianol,
photoanethole)
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Chalconoids (e.g.,
isoliquiritigenin,
phloretin,
phlorizin (phloridzin),
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Coumestans (e.g.,
coumestrol,
psoralidin)
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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)
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Lavender oil
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enterodiol,
enterolactone,
nyasol (cis-hinokiresinol))
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Metalloestrogens (e.g.,
cadmium)
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alternariol,
dieldrin,
endosulfan,
fenarimol,
HPTE,
methiocarb,
methoxychlor,
triclocarban,
triclosan)
-
Phytosteroids (e.g.,
digitoxin (
digitalis),
diosgenin,
guggulsterone)
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Phytosterols (e.g.,
β-sitosterol,
campesterol,
stigmasterol)
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Resorcylic acid lactones (e.g.,
zearalanone,
α-zearalenol,
β-zearalenol,
zearalenone,
zeranol (α-zearalanol),
taleranol (teranol, β-zearalanol))
-
Steroid-like (e.g.,
deoxymiroestrol,
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Stilbenoids (e.g.,
resveratrol,
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BPA,
BPF,
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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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