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Edogestrone

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Edogestrone
Clinical data
Other namesEdogesterone; PH-218; 17α-Acetoxy-3,3-ethylenedioxy-6-methylpregn-5-en-20-one
Drug classProgestogen;Progestogen ester
Identifiers
  • [(8'R,9'S,10'R,13'S,14'S,17'R)-17'-acetyl-6',10',13'-trimethylspiro[1,3-dioxolane-2,3'-2,4,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene]-17'-yl] acetate
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC26H38O5
Molar mass430.585 g·mol−1
3D model (JSmol)
  • CC1=C2CC3(CCC2(C4CCC5(C(C4C1)CCC5(C(=O)C)OC(=O)C)C)C)OCCO3
  • InChI=1S/C26H38O5/c1-16-14-19-20(23(4)10-11-25(15-22(16)23)29-12-13-30-25)6-8-24(5)21(19)7-9-26(24,17(2)27)31-18(3)28/h19-21H,6-15H2,1-5H3/t19-,20+,21+,23-,24+,26+/m1/s1
  • Key:UOYMGHSCINLOBK-ZKKYLISVSA-N

Edogestrone (INNTooltip International Nonproprietary Name,BANTooltip British Approved Name) (developmental code namePH-218), oredogesterone, also known as17α-acetoxy-3,3-ethylenedioxy-6-methylpregn-5-en-20-one, is asteroidalprogestin andantiandrogen of the17α-hydroxyprogesterone group which wassynthesized in 1964 but was never marketed.[1][2] Similarly to the structurally related steroidcyproterone acetate, edogestrone binds directly to theandrogen receptor andantagonizes it, displacingandrogens liketestosterone from the receptor, though not as potently as cyproterone acetate.[3] The drug has also been found to suppressandrogen production, likely viaprogesterone receptor activation-mediatedantigonadotropic activity.[4]

See also

[edit]

References

[edit]
  1. ^Elks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 478–.ISBN 978-1-4757-2085-3.
  2. ^Geller J, McCoy K (February 1974). "Biologic and biochemical effects of anti-androgens on rat ventral prostate".Acta Endocrinologica.75 (2):385–397.doi:10.1530/acta.0.0750385.PMID 4406552.
  3. ^Spring-Mills E, Hafez ES (1 January 1980).Male accessory sex glands: biology and pathology. Elsevier/North-Holland Biomedical Press. p. 500.ISBN 9780444801678.
  4. ^Castro JE (9 March 2013).The Treatment of Prostatic Hypertrophy and Neoplasia. Springer Science & Business Media. pp. 39–.ISBN 978-94-015-7190-6.Geller has also demonstrated significant decreases in plasma or urine testosterone glucuronide levels following the administration of three other anti-androgens. These include Delalutin, Chlormadinone acetate, and PH-218. It would appear that decreased androgen production is a property shared by all anti-androgens to date.
ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists

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