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Edogestrone

Edogestrone (INNTooltip International Nonproprietary Name, BANTooltip British Approved Name) (developmental code name PH-218), or edogesterone, also known as 17α-acetoxy-3,3-ethylenedioxy-6-methylpregn-5-en-20-one, is a steroidal progestin and antiandrogen of the 17α-hydroxyprogesterone group which was synthesized in 1964 but was never marketed.[1][2] Similarly to the structurally related steroid cyproterone acetate, edogestrone binds directly to the androgen receptor and antagonizes it, displacing androgens like testosterone from the receptor, though not as potently as cyproterone acetate.[3] The drug has also been found to suppress androgen production, likely via progesterone receptor activation-mediated antigonadotropic activity.[4]

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
  • 809-01-8
PubChem CID
  • 20055315
ChemSpider
  • 92030
UNII
  • 9014UFK50C
Chemical and physical data
FormulaC26H38O5
Molar mass430.585 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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

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.

edogestrone, inntooltip, international, nonproprietary, name, bantooltip, british, approved, name, developmental, code, name, edogesterone, also, known, 17α, acetoxy, ethylenedioxy, methylpregn, steroidal, progestin, antiandrogen, 17α, hydroxyprogesterone, gro. Edogestrone INNTooltip International Nonproprietary Name BANTooltip British Approved Name developmental code name PH 218 or edogesterone also known as 17a acetoxy 3 3 ethylenedioxy 6 methylpregn 5 en 20 one is a steroidal progestin and antiandrogen of the 17a hydroxyprogesterone group which was synthesized in 1964 but was never marketed 1 2 Similarly to the structurally related steroid cyproterone acetate edogestrone binds directly to the androgen receptor and antagonizes it displacing androgens like testosterone from the receptor though not as potently as cyproterone acetate 3 The drug has also been found to suppress androgen production likely via progesterone receptor activation mediated antigonadotropic activity 4 EdogestroneClinical dataOther namesEdogesterone PH 218 17a Acetoxy 3 3 ethylenedioxy 6 methylpregn 5 en 20 oneDrug classProgestogen Progestogen esterIdentifiersIUPAC name 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 acetateCAS Number809 01 8PubChem CID20055315ChemSpider92030UNII9014UFK50CChemical and physical dataFormulaC 26H 38O 5Molar mass430 585 g mol 13D model JSmol Interactive imageSMILES CC1 C2CC3 CCC2 C4CCC5 C C4C1 CCC5 C O C OC O C C C OCCO3InChI 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 s1Key UOYMGHSCINLOBK ZKKYLISVSA NSee also editSteroidal antiandrogen List of progestogens List of steroidal antiandrogens List of progestogen estersReferences edit 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 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 Spring Mills E Hafez ES 1 January 1980 Male accessory sex glands biology and pathology Elsevier North Holland Biomedical Press p 500 ISBN 9780444801678 Castro JE 9 March 2013 The Treatment of Prostatic Hypertrophy and Neoplasia Springer Science amp 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 nbsp This article about a steroid is a stub You can help Wikipedia by expanding it vte nbsp This drug article relating to the genito urinary system is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Edogestrone amp oldid 1184915589, wikipedia, wiki, book, books, library,

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