From Wikipedia, the free encyclopedia
Chemical compound
Cyclodiol
Other names ZK-115194; Cycloestradiol; 14α,17α-Ethano-17β-estradiol; 14α,17α-Ethanoestra-1,3,5(10)-triene-3,17β-diol; 14,21-Cyclo-19-norpregna-1,3,5(10)-triene-3,17α-diol
Routes of administration
By mouth
[1]
Drug class
Estrogen
Bioavailability 33 ± 19%
[1]
Elimination half-life 28.7 hours
[1]
(8R ,9S ,13S )-13-Methyl-7,8,9,11,12,13,15,16-octahydro-14,17-ethanocyclopenta[a ]phenanthrene-3,17(6H )-diol
CAS Number
PubChem
CID
ChemSpider
UNII
CompTox Dashboard (
EPA )
Formula C 20 H 26 O 2
Molar mass 298.426 g·mol−1 3D model (
JSmol )
C[C@]12CC[C@H]3[C@H](C14CCC2(CC4)O)CCC5=C3C=CC(=C5)O
InChI=1S/C20H26O2/c1-18-7-6-16-15-4-3-14(21)12-13(15)2-5-17(16)19(18)8-10-20(18,22)11-9-19/h3-4,12,16-17,21-22H,2,5-11H2,1H3/t16-,17-,18+,19?,20?/m1/s1
Key:YGXXZMDWSWSCSI-UYUJGIFYSA-N
Cyclodiol (developmental code name ZK-115194 ; also known as 14α,17α-ethano-17β-estradiol ) is a
synthetic
estrogen which was studied in the 1990s and was never marketed.
[2]
[1]
[3] It is a
derivative of
estradiol with a
bridge between the C14α and C17α positions.
[2]
[1]
[3]
[4] Cyclodiol has 100% of the
relative binding affinity of estradiol for the human
ERα and similar
transactivational capacity as estradiol at the receptor.
[2] It has comparable
potency to estradiol when administered by
subcutaneous injection .
[2] The drug shows
genotoxicity similarly to estradiol.
[2]
[4] Cyclodiol showed an
absolute bioavailability of 33 ± 19% and an
elimination half-life of 28.7 hours in
pharmacokinetic studies in women.
[1]
See also
References
^
a
b
c
d
e
f Baumann A, Fuhrmeister A, Brudny-Klöppel M, Draeger C, Bunte T, Kuhnz W (October 1996). "Comparative pharmacokinetics of two new steroidal estrogens and ethinylestradiol in postmenopausal women". Contraception . 54 (4): 235–242.
doi :
10.1016/S0010-7824(96)00194-1 .
PMID
8922877 .
^
a
b
c
d
e Oettel M, Schillinger E (6 December 2012).
Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen . Springer Science & Business Media. pp. 10, 15, 76, 329, 332.
ISBN
978-3-642-60107-1 .
^
a
b Lang R, Reimann R (1993). "Studies for a genotoxic potential of some endogenous and exogenous sex steroids. I. Communication: examination for the induction of gene mutations using the Ames Salmonella/microsome test and the HGPRT test in V79 cells". Environmental and Molecular Mutagenesis . 21 (3): 272–304.
doi :
10.1002/em.2850210311 .
PMID
8462531 .
S2CID
39049586 .
^
a
b Hundal BS, Dhillon VS, Sidhu IS (March 1997). "Genotoxic potential of estrogens". Mutation Research . 389 (2–3): 173–181.
doi :
10.1016/S1383-5718(96)00144-1 .
PMID
9093381 .
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