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Cyclotriol

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
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]
Eliminationhalf-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
PubChemCID
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 nameZK-136295; also known as14α,17α-ethanoestriol) is asyntheticestrogen which was studied in the 1990s and was never marketed.[2][1][3][4] It is aderivative ofestriol with abridge between the C14α and C17α positions.[2][1][3][5] The drug has 40% of therelative binding affinity of estradiol for the humanERα.[2] It showed anabsolute bioavailability of 40% with highinterindividual variability and anelimination half-life of 12.3 hours inpharmacokinetic studies in women.[1]

See also

[edit]

References

[edit]
  1. ^abcdefBaumann 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. ^abcOettel 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. ^abLang 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.Bibcode:1993EnvMM..21..272L.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.Bibcode:1996EnvMM..28..133R.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.Bibcode:1997MRGTE.389..173H.doi:10.1016/S1383-5718(96)00144-1.PMID 9093381.
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown

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