Cyclotriol

Cyclotriol
Clinical data
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
Drug class	Estrogen
Pharmacokinetic data
Bioavailability	40%
Elimination half-life	12.3 hours
Identifiers
	IUPAC name (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	135768-83-1;
PubChem CID	15967764;
ChemSpider	8601225;
UNII	743NA857FA;
CompTox Dashboard (EPA)	DTXSID00929146 ;
Chemical and physical data
Formula	C20H26O3
Molar mass	314.425 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@]12CC[C@H]3[C@H]([C@@]14CC[C@@]2([C@@H](C4)O)O)CCC5=C3C=CC(=C5)O;
	InChI 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]

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
administrationBy mouth^[1]

Drug classEstrogen

Bioavailability40%^[1]

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Cyclotriol

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Clinical data

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
Pharmacokinetic data
Bioavailability	40%^[1]
Elimination half-life	12.3 hours^[1]
Identifiers
IUPAC name (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	135768-83-1
PubChem CID	15967764
ChemSpider	8601225
UNII	743NA857FA
CompTox Dashboard (EPA)	DTXSID00929146
Chemical and physical data
Formula	C₂₀H₂₆O₃
Molar mass	314.425 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C[C@]12CC[C@H]3[C@H]([C@@]14CC[C@@]2([C@@H](C4)O)O)CCC5=C3C=CC(=C5)O
InChI 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