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Bolandiol

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Bolandiol
Clinical data
Other names19-Norandrostenediol; 19-Nor-4-androstene-3β,17β-diol; Estr-4-ene-3β,17β-diol; 3β-Dihydronandrolone
Identifiers
  • (3S,8R,9S,10R,13S,14S,17S)-13-methyl-1,2,3,6,7,8,9,10,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,17-diol
CAS Number
PubChemCID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC18H28O2
Molar mass276.420 g·mol−1
3D model (JSmol)
  • O[C@@H]4/C=C2\[C@@H]([C@H]1CC[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)CC4
  • InChI=1S/C18H28O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,12-17,19-20H,2-9H2,1H3/t12-,13-,14+,15+,16-,17-,18-/m0/s1
  • Key:CMXKUJNZWYTFJN-XFUVECHXSA-N

Bolandiol (INN, also known as19-nor-4-androstenediol,estr-4-ene-3β,17β-diol, or3β-dihydronandrolone) is ananabolic-androgenic steroid (AAS) that was never marketed.[1] However, adipropionateesterderivative,bolandiol dipropionate, has been marketed.[1][2] Bolandiol and its dipropionate ester are unique among AASs in that they reportedly also possessesestrogenic andprogestogenic activity.[3][4]

Bolandiol is on theWorld Anti-Doping Agency's list of prohibited substances,[5] and is therefore banned from use in most major sports. It is a potentialmetabolic precursor (via 3β-HSD) tonandrolone or a derivative ofnandrolone (via 3β-hydroxy-steroid:NADP+ 3-oxidoreductase).[6] However, several clinical studies have concluded that bolandiol does not alter strength, body composition, or exercise performance.[7][8]

See also

[edit]

References

[edit]
  1. ^abElks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 899–.ISBN 978-1-4757-2085-3.
  2. ^Hyde TE, Gengenbach MS (2007).Conservative Management of Sports Injuries. Jones & Bartlett Learning. pp. 1100–.ISBN 978-0-7637-3252-3.
  3. ^Action QA, ed. (9 January 2012).Hormones: Advances in Research and Application (2011 ed.). ScholarlyEditions. pp. 59–.ISBN 978-1-4649-2242-8.
  4. ^Attardi BJ, Page ST, Hild SA, Coss CC, Matsumoto AM (February 2010)."Mechanism of action of bolandiol (19-nortestosterone-3beta,17beta-diol), a unique anabolic steroid with androgenic, estrogenic, and progestational activities".The Journal of Steroid Biochemistry and Molecular Biology.118 (3):151–61.doi:10.1016/j.jsbmb.2009.11.008.PMC 2831543.PMID 19941958.
  5. ^"The World Anti-Doping Code: The 2012 Prohibited List"(PDF).World Anti-Doping Agency. Archived fromthe original(PDF) on 2012-05-13. Retrieved2012-07-17.
  6. ^Dehennin L, Bonnaire Y, Plou P (January 2002). "Human nutritional supplements in the horse: comparative effects of 19-norandrostenedione and 19-norandrostenediol on the 19-norsteroid profile and consequences for doping control".Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences.766 (2):257–263.doi:10.1016/S0378-4347(01)00506-0.PMID 11824814.
  7. ^Van Gammeren D, Falk D, Antonio J (May 2001). "The effects of supplementation with 19-nor-4-androstene-3,17-dione and 19-nor-4-androstene-3,17-diol on body composition and athletic performance in previously weight-trained male athletes".European Journal of Applied Physiology.84 (5):426–431.doi:10.1007/s004210100395.PMID 11417430.S2CID 13129479.
  8. ^van Gammeren D, Falk D, Antonio J (September 2002). "Effects of norandrostenedione and norandrostenediol in resistance-trained men".Nutrition.18 (9):734–737.doi:10.1016/s0899-9007(02)00834-1.PMID 12297208.
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