Jump to content

Gestadienol acetate

Add links
From Wikipedia, the free encyclopedia
Gestadienol acetate
Clinical data
Other namesCIBA-31458-Ba; CIBA-31458; Norhydroxy-δ6-progesterone acetate; 6-Dehydro-17α-acetoxy-19-norprogesterone; 17α-Acetoxy-19-norpregn-4,6-diene-3,20-dione
Routes of
administration		By mouth[1][2]
Drug classProgestogen;Progestogen ester
Identifiers
  • [(8R,9S,10R,13S,14S,17R)-17-acetyl-13-methyl-3-oxo-1,2,8,9,10,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl] acetate
CAS Number
PubChemCID
ECHA InfoCard100.224.529Edit this at Wikidata
Chemical and physical data
FormulaC22H28O4
Molar mass356.462g·mol−1
3D model (JSmol)
  • CC(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C=CC4=CC(=O)CC[C@H]34)C)OC(=O)C
  • InChI=1S/C22H28O4/c1-13(23)22(26-14(2)24)11-9-20-19-6-4-15-12-16(25)5-7-17(15)18(19)8-10-21(20,22)3/h4,6,12,17-20H,5,7-11H2,1-3H3/t17-,18+,19+,20-,21-,22-/m0/s1
  • Key:TUFRQQROGGMVOC-ZCPXKWAGSA-N

Gestadienol acetate(developmental code nameCIBA-31458-BaorCIBA-31458) anorally activeprogestinwhich was described in the literature in 1967 and was never marketed.[3][1][2][4][5]It has noandrogenicorestrogeniceffects.[6]The effects of gestadienol acetate on theendometriumand its generalpharmacologywere studied in aclinical trialin women.[2][5]It has also been studied in a clinical trial forbenign prostatic hyperplasiain men, but was ineffective.[6]

Chemistry

[edit]
See also:List of progestogens,List of progestogen esters,andProgestogen ester

Gestadienol acetate, also known as norhydroxy-δ6-progesterone acetate, 6-dehydro-17α-hydroxy-19-norprogesterone 17α-acetate, or 17α-hydroxy-19-norpregn-4,6-diene-3,20-dione 17α-acetate, is asyntheticnorpregnanesteroidand aderivativeofprogesterone.[3]It is specifically a combined derivative of17α-hydroxyprogesteroneand19-norprogesterone,or ofgestronol(17α-hydroxy-19-norprogesterone), with anacetateesterat the C17α position and adouble bondbetween the C6 and C7 positions.[3]Gestadienol acetate is the C17αacetateesterofgestadienol.[3]Analoguesof gestadienol acetate includealgestone acetophenide(dihydroxyprogesterone acetophenide),demegestone,gestonorone caproate(norhydroxyprogesterone caproate),hydroxyprogesterone acetate,hydroxyprogesterone caproate,nomegestrol acetate,norgestomet,andsegesterone acetate(nestorone).[3]

References

[edit]
  1. ^abDesaulles PA, Krähenbühl C (1967). "Biological Properties of a New Progesterone Analogue".European Journal of Endocrinology.56(1 Suppl): S143.doi:10.1530/acta.0.056S143.ISSN0804-4643.
  2. ^abcGupta A (January 1967)."Effect of the new progestogen, CIBA 31458 on the human endometrium"(PDF).Journal of Reproduction and Fertility.14(3). Cambridge, England: 530.
  3. ^abcdeElks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies.Springer. p. 659.ISBN978-1-4757-2085-3.
  4. ^Petrow V (December 1970). "The contraceptive progestagens".Chemical Reviews.70(6): 713–726.doi:10.1021/cr60268a004.PMID4098492.
  5. ^abHeusler K, Kalvoda J (August 1996). "Between basic and applied research: Ciba's involvement in steroids in the 1950s and 1960s".Steroids.61(8): 492–503.doi:10.1016/0039-128x(96)00040-2.PMID8870170.S2CID37228396.
  6. ^abHald T, From A (1972). "Benign prostatic hypertrophy treated with a gestagen. A double-blind clinical trial with randomized allocation".Scandinavian Journal of Urology and Nephrology.6(Suppl 157): 157–163.doi:10.3109/00365597209133659.PMID4118753.
Stub icon

Thisdrugarticle relating to thegenito-urinary systemis astub.You can help Wikipedia byexpanding it.

Stub icon

This article about asteroidis astub.You can help Wikipedia byexpanding it.

Retrieved from "https://en.wikipedia.org/w/index.php?title=Gestadienol_acetate&oldid=1169778917"