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'''Cyclotriol''' (developmental code name '''ZK-136295'''; also known as '''14α,17α-ethanoestriol''') is a [[synthetic compound|synthetic]] [[estrogen (medication)|estrogen]] which was studied in the 1990s and was never marketed.<ref name="OettelSchillinger2012">{{cite book|author1=Michael Oettel|author2=Ekkehard Schillinger|title=Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen|url=https://books.google.com/books?id=wBvyCAAAQBAJ&pg=PA10|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-60107-1|pages=10,15,76,331–332}}</ref><ref name="pmid8922877">{{cite journal | vauthors = Baumann A, Fuhrmeister A, Brudny-Klöppel M, Draeger C, Bunte T, Kuhnz W | title = Comparative pharmacokinetics of two new steroidal estrogens and ethinylestradiol in postmenopausal women | journal = Contraception | volume = 54 | issue = 4 | pages = 235–42 | date = October 1996 | pmid = 8922877 | doi = 10.1016/S0010-7824(96)00194-1 }}</ref><ref name="LangReimann1993">{{cite journal|last1=Lang|first1=Rainer|last2=Reimann|first2=Roland|title=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|journal=Environmental and Molecular Mutagenesis|volume=21|issue=3|year=1993|pages=272–304|issn=0893-6692|doi=10.1002/em.2850210311|pmid=8462531|s2cid=39049586}}</ref><ref name="pmid8844995">{{cite journal | vauthors = Reimann R, Kalweit S, Lang R | title = 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 | journal = Environ. Mol. Mutagen. | volume = 28 | issue = 2 | pages = 133–44 | date = 1996 | pmid = 8844995 | doi = 10.1002/(SICI)1098-2280(1996)28:2<133::AID-EM10>3.0.CO;2-G | s2cid = 10326219 }}</ref> It is a [[chemical derivative|derivative]] of [[estriol (medication)|estriol]] with a [[bridged compounds|bridge]] between the C14α and C17α positions.<ref name="OettelSchillinger2012" /><ref name="pmid8922877" /><ref name="LangReimann1993" /><ref name="pmid9093381">{{cite journal | vauthors = Hundal BS, Dhillon VS, Sidhu IS | title = Genotoxic potential of estrogens | journal = Mutat. Res. | volume = 389 | issue = 2–3 | pages = 173–81 | date = March 1997 | pmid = 9093381 | doi = 10.1016/S1383-5718(96)00144-1 }}</ref> The drug has 40% of the [[relative binding affinity]] of estradiol for the human [[ERα]].<ref name="OettelSchillinger2012" /> It showed an [[absolute bioavailability]] of 40% with high [[interindividual variability]] and an [[elimination half-life]] of 12.3&nbsp;hours in [[pharmacokinetic]] studies in women.<ref name="pmid8922877" />
'''Cyclotriol''' (developmental code name '''ZK-136295'''; also known as '''14α,17α-ethanoestriol''') is a [[synthetic compound|synthetic]] [[estrogen (medication)|estrogen]] which was studied in the 1990s and was never marketed.<ref name="OettelSchillinger2012">{{cite book | vauthors = Oettel M, Schillinger E |title=Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen|url=https://books.google.com/books?id=wBvyCAAAQBAJ&pg=PA10|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-60107-1|pages=10,15,76,331–332}}</ref><ref name="pmid8922877">{{cite journal | vauthors = Baumann A, Fuhrmeister A, Brudny-Klöppel M, Draeger C, Bunte T, Kuhnz W | title = Comparative pharmacokinetics of two new steroidal estrogens and ethinylestradiol in postmenopausal women | journal = Contraception | volume = 54 | issue = 4 | pages = 235–242 | date = October 1996 | pmid = 8922877 | doi = 10.1016/S0010-7824(96)00194-1 }}</ref><ref name="LangReimann1993">{{cite journal | vauthors = Lang R, Reimann R | title = 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 | journal = Environmental and Molecular Mutagenesis | volume = 21 | issue = 3 | pages = 272–304 | year = 1993 | pmid = 8462531 | doi = 10.1002/em.2850210311 | s2cid = 39049586 }}</ref><ref name="pmid8844995">{{cite journal | vauthors = Reimann R, Kalweit S, Lang R | title = 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 | journal = Environmental and Molecular Mutagenesis | volume = 28 | issue = 2 | pages = 133–144 | date = 1996 | pmid = 8844995 | doi = 10.1002/(SICI)1098-2280(1996)28:2<133::AID-EM10>3.0.CO;2-G | s2cid = 10326219 }}</ref> It is a [[chemical derivative|derivative]] of [[estriol (medication)|estriol]] with a [[bridged compounds|bridge]] between the C14α and C17α positions.<ref name="OettelSchillinger2012" /><ref name="pmid8922877" /><ref name="LangReimann1993" /><ref name="pmid9093381">{{cite journal | vauthors = Hundal BS, Dhillon VS, Sidhu IS | title = Genotoxic potential of estrogens | journal = Mutation Research | volume = 389 | issue = 2–3 | pages = 173–181 | date = March 1997 | pmid = 9093381 | doi = 10.1016/S1383-5718(96)00144-1 }}</ref> The drug has 40% of the [[relative binding affinity]] of estradiol for the human [[ERα]].<ref name="OettelSchillinger2012" /> It showed an [[absolute bioavailability]] of 40% with high [[interindividual variability]] and an [[elimination half-life]] of 12.3&nbsp;hours in [[pharmacokinetic]] studies in women.<ref name="pmid8922877" />


==See also==
== See also ==
* [[List of estrogens#Estriol derivatives|List of estrogens § Estriol derivatives]]
* [[List of estrogens#Estriol derivatives|List of estrogens § Estriol derivatives]]
* [[Cyclodiol]]
* [[Cyclodiol]]


==References==
== References ==
{{Reflist}}
{{Reflist}}



{{Estrogen receptor modulators}}
{{Estrogen receptor modulators}}
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[[Category:Synthetic estrogens]]
[[Category:Synthetic estrogens]]
[[Category:Triols]]
[[Category:Triols]]



{{Steroid-stub}}
{{Steroid-stub}}

Latest revision as of 08:58, 1 July 2023

Cyclotriol
Clinical data
Other namesZK-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 classEstrogen
Pharmacokinetic data
Bioavailability40%[1]
Elimination half-life12.3 hours[1]
Identifiers
  • (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)
Chemical and physical data
FormulaC20H26O3
Molar mass314.425 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 an elimination half-life of 12.3 hours in pharmacokinetic studies in women.[1]

See also

[edit]

References

[edit]
  1. ^ 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.
  2. ^ a b c 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, 331–332. ISBN 978-3-642-60107-1.
  3. ^ 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.
  4. ^ 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". Environmental and Molecular Mutagenesis. 28 (2): 133–144. doi:10.1002/(SICI)1098-2280(1996)28:2<133::AID-EM10>3.0.CO;2-G. PMID 8844995. S2CID 10326219.
  5. ^ 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.
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