Cyclodiol - Misplaced Pages

Chemical compound Pharmaceutical compound

Cyclodiol
Clinical data

Other names	ZK-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
Drug class	Estrogen
Pharmacokinetic data
Bioavailability	33 ± 19%
Elimination half-life	28.7 hours
Identifiers
IUPAC name (8R,9S,13S)-13-Methyl-7,8,9,11,12,13,15,16-octahydro-14,17-ethanocyclopentaphenanthrene-3,17(6H)-diol
CAS Number	116229-13-1
PubChem CID	146627
ChemSpider	18788501
UNII	GH2S6QPT38
CompTox Dashboard (EPA)	DTXSID50921978
Chemical and physical data
Formula	C₂₀H₂₆O₂
Molar mass	298.426 g·mol
3D model (JSmol)	Interactive image
SMILES C12CC3(C14CCC2(CC4)O)CCC5=C3C=CC(=C5)O
InChI 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

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. It is a derivative of estradiol with a bridge between the C14α and C17α positions. Cyclodiol has 100% of the relative binding affinity of estradiol for the human ERα and similar transactivational capacity as estradiol at the receptor. It has comparable potency to estradiol when administered by subcutaneous injection. The drug shows genotoxicity similarly to estradiol. Cyclodiol showed an absolute bioavailability of 33 ± 19% and an elimination half-life of 28.7 hours in pharmacokinetic studies in women.

References

^ 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.
^ 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, 329, 332. ISBN 978-3-642-60107-1.
^ 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.
^ 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.

ERTooltip Estrogen receptor

Agonists

Mixed
(SERMsTooltip Selective estrogen receptor modulators)

Antagonists

GPERTooltip G protein-coupled estrogen receptor

Agonists	2-Methoxyestradiol 7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Aldosterone Atrazine Bisphenol A Daidzein DDT (p,p'-DDT, o',p'-DDE) Diarylpropionitrile Equol Estradiol Ethinylestradiol Fulvestrant (ICI-182780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Niacin Niacinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol STX Tamoxifen Tectoridin
Antagonists	CCL18 Estriol G-15 G-36 MIBE
Unknown	Diethylstilbestrol Zearalenone

See also: Receptor/signaling modulators; Estrogens and antiestrogens; Androgen receptor modulators; Progesterone receptor modulators; List of estrogens

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