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Cyclodiol

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
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]
Eliminationhalf-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
PubChemCID
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

Cyclodiol (developmental code nameZK-115194; also known as14α,17α-ethano-17β-estradiol) is asyntheticestrogen which was studied in the 1990s and was never marketed.[2][1][3] It is aderivative ofestradiol with abridge between the C14α and C17α positions.[2][1][3][4] Cyclodiol has 100% of therelative binding affinity of estradiol for the humanERα and similartransactivational capacity as estradiol at the receptor.[2] It has comparablepotency to estradiol when administered bysubcutaneous injection.[2] The drug showsgenotoxicity similarly to estradiol.[2][4] Cyclodiol showed anabsolute bioavailability of 33 ± 19% and anelimination half-life of 28.7 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. ^abcdeOettel 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.
  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. ^abHundal 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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