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Cyclotriol Other names ZK-136295; Cycloestriol; 14α,17α-Ethanoestriol; 14α,17α-Ethanoestra-1,3,5(10)-triene-3,16α,17β-triol; 14,21-Cyclo-19-norpregna-1,3,5(10)-triene-3,16α,17α-triol Routes of administration By mouth [ 1] Drug class Estrogen Bioavailability 40%[ 1] Elimination half-life 12.3 hours[ 1]
(8R ,9S ,13S ,14S ,16R ,17R )-13-Methyl-7,8,9,11,12,13,15,16-octahydro-14,17-ethanocyclopenta[a ]phenanthrene-3,16,17(6H )-triol
CAS Number PubChem CID ChemSpider UNII CompTox Dashboard (EPA ) Formula C 20 H 26 O 3 Molar mass 314.425 g/mol g·mol−1 3D model (JSmol )
C[C@]12CC[C@H]3[C@H]([C@@]14CC[C@@]2([C@@H](C4)O)O)CCC5=C3C=CC(=C5)O
InChI=1S/C20H26O3/c1-18-7-6-15-14-4-3-13(21)10-12(14)2-5-16(15)19(18)8-9-20(18,23)17(22)11-19/h3-4,10,15-17,21-23H,2,5-9,11H2,1H3/t15-,16-,17-,18+,19+,20+/m1/s1
Key:PAMNOUDFJQSYMD-MUJBESKKSA-N
Cyclotriol (developmental code name ZK-136295 ; also known as 14α,17α-ethanoestriol ) is a synthetic estrogen which was studied in the 1990s and was never marketed.[ 2] [ 1] [ 3] [ 4] It is a derivative of estriol with a bridge between the C14α and C17α positions.[ 2] [ 1] [ 3] [ 5] The drug has 40% of the relative binding affinity of estradiol for the human ERα .[ 2] It showed an absolute bioavailability of 40% with high interindividual variability and a terminal half-life of 12.3 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): 235–42. doi :10.1016/S0010-7824(96)00194-1 . PMID 8922877 .
^ a b c Michael Oettel; Ekkehard Schillinger (6 December 2012). Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen . Springer Science & Business Media. pp. 10, 15, 76, 331–332. ISBN 978-3-642-60107-1 .
^ a b Lang, Rainer; Reimann, Roland (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 . ISSN 0893-6692 .
^ Reimann R, Kalweit S, Lang R (1996). "Studies for a genotoxic potential of some endogenous and exogenous sex steroids. II. Communication: examination for the induction of cytogenetic damage using the chromosomal aberration assay on human lymphocytes in vitro and the mouse bone marrow micronucleus test in vivo". Environ. Mol. Mutagen . 28 (2): 133–44. doi :10.1002/(SICI)1098-2280(1996)28:2<133::AID-EM10>3.0.CO;2-G . PMID 8844995 .
^ Hundal BS, Dhillon VS, Sidhu IS (March 1997). "Genotoxic potential of estrogens". Mutat. Res . 389 (2–3): 173–81. 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
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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
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Atrimustine
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Butolame
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Cyclodiol
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Epimestrol
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RU-16117
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Lavender oil
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Steroid -like (e.g., deoxymiroestrol , miroestrol )
Stilbenoids (e.g., resveratrol , rhaponticin )
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Mixed (SERMs Tooltip Selective estrogen receptor modulators ) Antagonists
Coregulator-binding modulators: ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Agonists Antagonists Unknown