Cyclodiol

Chemical compound From Wikipedia, the free encyclopedia

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]

Other namesZK-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
administrationBy mouth[1]
Drug classEstrogen
Bioavailability33 ± 19%[1]
Quick facts Clinical data, Other names ...
Cyclodiol
Clinical data
Other namesZK-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 classEstrogen
Pharmacokinetic data
Bioavailability33 ± 19%[1]
Elimination half-life28.7 hours[1]
Identifiers
  • (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)
Chemical and physical data
FormulaC20H26O2
Molar mass298.426 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
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