Bolandiol

{{Short description|Chemical compound}}

{{Drugbox

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| IUPAC_name = (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

| image = Bolandiol.svg

| image_class = skin-invert-image

| width = 250

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| CAS_number_Ref =

| CAS_number = 19793-20-5

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| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 49SD6G16U5

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| PubChem = 9835303

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| ChemSpiderID_Ref =

| ChemSpiderID = 8011024

| ChEBI = 145661

| ChEMBL = 2106664

| C=18 | H=28 | O=2

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| smiles = 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

| StdInChI_Ref =

| StdInChI = 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

| StdInChIKey_Ref =

| StdInChIKey = CMXKUJNZWYTFJN-XFUVECHXSA-N

| synonyms = 19-Norandrostenediol; 19-Nor-4-androstene-3β,17β-diol; Estr-4-ene-3β,17β-diol; 3β-Dihydronandrolone

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Bolandiol (INN, also known as 19-nor-4-androstenediol, estr-4-ene-3β,17β-diol, or 3β-dihydronandrolone) is an anabolic-androgenic steroid (AAS) that was never marketed.{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA899|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=899–}} However, a dipropionate ester derivative, bolandiol dipropionate, has been marketed.{{cite book| vauthors = Hyde TE, Gengenbach MS |title=Conservative Management of Sports Injuries|url=https://books.google.com/books?id=uzPwfNYyjjUC&pg=PA1100|year=2007|publisher=Jones & Bartlett Learning|isbn=978-0-7637-3252-3|pages=1100–}} Bolandiol and its dipropionate ester are unique among AASs in that they reportedly also possesses estrogenic and progestogenic activity.{{cite book | veditors = Action QA |title=Hormones: Advances in Research and Application | edition = 2011 |url=https://books.google.com/books?id=zhzrlLrsI4AC&pg=PT59|date=9 January 2012|publisher=ScholarlyEditions|isbn=978-1-4649-2242-8 |pages=59–}}{{cite journal | vauthors = Attardi BJ, Page ST, Hild SA, Coss CC, Matsumoto AM | title = Mechanism of action of bolandiol (19-nortestosterone-3beta,17beta-diol), a unique anabolic steroid with androgenic, estrogenic, and progestational activities | journal = The Journal of Steroid Biochemistry and Molecular Biology | volume = 118 | issue = 3 | pages = 151–61 | date = February 2010 | pmid = 19941958 | pmc = 2831543 | doi = 10.1016/j.jsbmb.2009.11.008 }}

Bolandiol is on the World Anti-Doping Agency's list of prohibited substances,{{cite web | url=http://www.wada-ama.org/Documents/World_Anti-Doping_Program/WADP-Prohibited-list/2012/WADA_Prohibited_List_2012_EN.pdf | title=The World Anti-Doping Code: The 2012 Prohibited List | publisher=World Anti-Doping Agency | access-date=2012-07-17 | url-status=dead | archive-url=https://web.archive.org/web/20120513020202/http://www.wada-ama.org/Documents/World_Anti-Doping_Program/WADP-Prohibited-list/2012/WADA_Prohibited_List_2012_EN.pdf | archive-date=2012-05-13 }} and is therefore banned from use in most major sports. It is a potential metabolic precursor to nandrolone.{{cite journal | vauthors = Dehennin L, Bonnaire Y, Plou P | title = 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 = Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences | volume = 766 | issue = 2 | pages = 257–263 | date = January 2002 | pmid = 11824814 | doi = 10.1016/S0378-4347(01)00506-0 }} However, several clinical studies have concluded that bolandiol does not alter strength, body composition, or exercise performance.{{cite journal | vauthors = Van Gammeren D, Falk D, Antonio J | title = 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 | journal = European Journal of Applied Physiology | volume = 84 | issue = 5 | pages = 426–431 | date = May 2001 | pmid = 11417430 | doi = 10.1007/s004210100395 | s2cid = 13129479 }}{{cite journal | vauthors = van Gammeren D, Falk D, Antonio J | title = Effects of norandrostenedione and norandrostenediol in resistance-trained men | journal = Nutrition | volume = 18 | issue = 9 | pages = 734–737 | date = September 2002 | pmid = 12297208 | doi = 10.1016/s0899-9007(02)00834-1 }}