Bolandiol

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Bolandiol
Bolandiol.svg
Names
Systematic IUPAC name
(3β,17β)-Estr-4-ene-3,17-diol
Other names
19-Norandrostenediol; 19-Nor-4-androstene-3β,17β-diol; (3β,17β)-Dihydroxyestr-4-ene; Estr-4-ene-3β,17β-diol
Identifiers
19793-20-5 YesY
ChEMBL ChEMBL2106664
ChemSpider 8011024
Jmol 3D model Interactive image
PubChem 9835303
Properties
C18H28O2
Molar mass 276.42 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Bolandiol (INN), also known as 19-norandrostenediol, is an anabolic-androgenic steroid (AAS) that was never marketed.[1] A dipropionate ester, bolandiol dipropionate (brand names Anabiol, Storinal; former developmental code name SC-7525), has been marketed.[1][2] Bolandiol (and its dipropionate ester) is unique among AAS in that it also possesses estrogenic and progestogenic activity.[3][4]

Bolandiol is on the World Anti-Doping Agency's list of prohibited substances,[5] and is therefore banned from use in most major sports. It is a potential metabolic precursor to nandrolone.[6] However, several clinical studies have concluded that bolandiol does not alter strength, body composition, or exercise performance.[7][8]

References[edit]

  1. ^ a b J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 899–. ISBN 978-1-4757-2085-3. 
  2. ^ Thomas E. Hyde; Marianne S. Gengenbach (2007). Conservative Management of Sports Injuries. Jones & Bartlett Learning. pp. 1100–. ISBN 978-0-7637-3252-3. 
  3. ^ Hormones: Advances in Research and Application: 2011 Edition. ScholarlyEditions. 9 January 2012. pp. 59–. ISBN 978-1-4649-2242-8. 
  4. ^ Attardi, BJ; Page, ST; Hild, SA; Coss, CC; Matsumoto, AM (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. Retrieved 2012-07-17. 
  6. ^ Dehennin, L.; Bonnaire, Y.; Plou, Ph. (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 766 (2): 257–263. doi:10.1016/S0378-4347(01)00506-0. 
  7. ^ Van Gammeren, D; Falk, D; Antonio, J (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): 426–31. doi:10.1007/s004210100395. PMID 11417430. 
  8. ^ Van Gammeren, D; Falk, D; Antonio, J (2002). "Effects of norandrostenedione and norandrostenediol in resistance-trained men". Nutrition 18 (9): 734–7. doi:10.1016/s0899-9007(02)00834-1. PMID 12297208.